MiMeDB: Showing metabocard for PS(14:1(9Z)/14:1(9Z)) (MMDBc0047244)

Microbial

Human

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:15:57 UTC

Update Date

2024-04-30 20:24:51 UTC

Metabolite ID

MMDBc0047244

Metabolite Identification

Common Name

PS(14:1(9Z)/14:1(9Z))

Description

PS(14:1(9Z)/14:1(9Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PS(14:1(9Z)/14:1(9Z)), in particular, consists of one chain of myristoleic acid at the C-1 position and one chain of myristoleic acid at the C-2 position. The myristoleic acid moiety is derived from milk fats, while the myristoleic acid moiety is derived from milk fats. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241203572D          

 48 47  0  0  1  0            999 V2000
   21.1271   -3.1271    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.2283   -4.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5532   -4.5893    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.8780   -4.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9034   -4.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2028   -4.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0263   -5.3689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5785   -4.1995    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.1887   -3.5243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9683   -4.8746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2536   -3.8097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9287   -4.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6038   -3.8097    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.1409   -5.3986    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.2999   -3.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0972   -3.6581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2999   -2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1074   -4.4924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2001   -4.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9146   -4.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6291   -4.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3436   -4.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0581   -4.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7726   -4.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4870   -4.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2015   -4.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9160   -4.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6304   -4.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3449   -4.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0594   -4.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7739   -4.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4884   -4.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4884   -3.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0236   -5.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7381   -5.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4525   -5.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1670   -5.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8815   -5.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5960   -5.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3105   -5.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0249   -5.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7394   -5.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4539   -5.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1684   -5.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8828   -5.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5974   -5.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3118   -5.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3118   -6.6064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  3  7  1  6  0  0  0
  8  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 11  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
  3 14  1  1  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 13  1  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32  6  1  0  0  0  0
 32 33  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47  7  1  0  0  0  0
 47 48  2  0  0  0  0
M  END

HMDB0012342
     RDKit          3D
PS(14:1(9Z)/14:1(9Z))
108107  0  0  0  0  0  0  0  0999 V2000
   13.8138    3.1237   -0.5470 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2767    3.0579   -0.6248 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7069    3.0566    0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2595    2.9305    0.8311 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2593    3.8529    0.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4523    3.6452   -0.6009 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3973    2.5064   -1.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1359    1.5915   -1.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4431    0.8628    0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4883   -0.0327    0.6292 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8951   -1.1734   -0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0339   -1.9460    0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9068   -1.2198    1.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9116   -0.7724    0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3153   -0.0494   -0.4615 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6344   -1.1783    0.4946 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5446   -0.9026   -0.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6105   -1.7614    0.2953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3421   -3.1982   -0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5400   -3.8150   -0.3472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8894   -5.1122   -1.2080 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.3211   -4.6028   -2.6440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5016   -5.7010   -0.6671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0340   -6.4412   -1.4251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1384   -6.9233   -0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7123   -8.3095   -0.2060 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9514   -8.1127    0.5509 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0765   -9.3672    0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3071   -9.5541    0.1379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6043  -10.4246    0.9848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7745   -1.4699   -0.3435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -0.9526    0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2203   -0.5267    1.1263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0008   -0.9775   -1.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1191   -0.0645   -0.8480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6458    1.3936   -0.9427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7920    2.2851   -0.5320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9563    2.1296    0.9821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2303    2.7191    1.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5295    4.1313    1.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8777    4.3749    1.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9133    4.5924    0.9435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8923    4.6234   -0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6135    3.5176   -1.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0105    3.2337   -0.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1360    2.7657    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0718    3.0493    0.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1770    4.0402   -1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.2777    2.2043   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9932    2.1251   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8809    3.9488   -1.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1486    2.1413    1.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0872    3.9210    1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9506    2.6937    1.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0518    1.8583    0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1591    4.8130    0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7083    4.4781   -0.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2590    1.7964   -1.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4266    2.8530   -2.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1283    0.9715   -2.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2624    2.2287   -1.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4645    0.3439   -0.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6839    1.6837    0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1157   -0.5582    1.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7661    0.5598    1.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6597   -1.8849   -0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3332   -0.8717   -1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7144   -2.3139    1.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6907   -2.8935    0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2318   -0.2413    1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3796   -1.7736    2.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7415   -1.3471   -1.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2561    0.1255   -0.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5530   -1.7458    1.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2375   -3.0907   -1.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2952   -3.7276    0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8603   -5.0760   -0.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0109   -6.3428    0.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8495   -7.1119   -0.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1110   -8.6774   -1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9008   -7.4307    1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7682   -8.5806    0.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4945  -10.6619    0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3742   -2.0442   -1.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5218   -0.8523   -2.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9356   -0.2027   -1.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6567   -0.3022    0.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4066    1.5902   -2.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7550    1.5117   -0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5201    3.3212   -0.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7160    1.9149   -1.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8738    1.1081    1.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1189    2.7515    1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2265    2.6418    2.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1117    2.0456    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3066    4.5051    0.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8304    4.7494    1.8298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9516    4.3705    2.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8859    4.8109    1.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8814    4.6805   -0.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3864    5.5877   -0.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0378    2.5541   -1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6585    3.8238   -2.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7164    4.0618   -1.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02241203572D          

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   18.1409   -5.3986    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.2999   -3.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0972   -3.6581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   22.1074   -4.4924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
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 47 48  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047244

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCC)OC(=O)CCCCCCC\C=C/CCCC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C34H62NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-32(36)42-27-30(28-43-46(40,41)44-29-31(35)34(38)39)45-33(37)26-24-22-20-18-16-14-12-10-8-6-4-2/h9-12,30-31H,3-8,13-29,35H2,1-2H3,(H,38,39)(H,40,41)/b11-9-,12-10-/t30-,31+/m1/s1

> <INCHI_KEY>
BPFJDFFAZFFCBH-QPBIGPORSA-N

> <FORMULA>
C34H62NO10P

> <MOLECULAR_WEIGHT>
675.8305

> <EXACT_MASS>
675.411133721

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
76.94190650553288

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-({[(2R)-2,3-bis[(9Z)-tetradec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoic acid

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
6.991388792232607

> <ALOGPS_LOGS>
-6.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.178396015655446

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4680339991787528

> <JCHEM_PKA_STRONGEST_BASIC>
9.376604467850061

> <JCHEM_POLAR_SURFACE_AREA>
171.68

> <JCHEM_REFRACTIVITY>
180.66300000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
34

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.02e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-3-{[(2R)-2,3-bis[(9Z)-tetradec-9-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012342
     RDKit          3D
PS(14:1(9Z)/14:1(9Z))
108107  0  0  0  0  0  0  0  0999 V2000
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   11.7069    3.0566    0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2595    2.9305    0.8311 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2593    3.8529    0.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9068   -1.2198    1.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5446   -0.9026   -0.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6105   -1.7614    0.2953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3421   -3.1982   -0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5400   -3.8150   -0.3472 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3211   -4.6028   -2.6440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5016   -5.7010   -0.6671 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1384   -6.9233   -0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7123   -8.3095   -0.2060 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.0765   -9.3672    0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.9563    2.1296    0.9821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2303    2.7191    1.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5295    4.1313    1.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8777    4.3749    1.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9133    4.5924    0.9435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8923    4.6234   -0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6135    3.5176   -1.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0105    3.2337   -0.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1360    2.7657    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0718    3.0493    0.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1770    4.0402   -1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7083    4.4781   -0.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7661    0.5598    1.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6907   -2.8935    0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2318   -0.2413    1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3796   -1.7736    2.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2375   -3.0907   -1.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2952   -3.7276    0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8603   -5.0760   -0.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0109   -6.3428    0.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8495   -7.1119   -0.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1110   -8.6774   -1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9008   -7.4307    1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7682   -8.5806    0.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4945  -10.6619    0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3742   -2.0442   -1.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5218   -0.8523   -2.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9356   -0.2027   -1.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6567   -0.3022    0.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4066    1.5902   -2.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7550    1.5117   -0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5201    3.3212   -0.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7160    1.9149   -1.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8738    1.1081    1.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1189    2.7515    1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2265    2.6418    2.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1117    2.0456    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3066    4.5051    0.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8304    4.7494    1.8298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9516    4.3705    2.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8859    4.8109    1.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8814    4.6805   -0.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3864    5.5877   -0.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0378    2.5541   -1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6585    3.8238   -2.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7164    4.0618   -1.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3658    2.3712   -1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8039    3.4072    1.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1529    2.5352    1.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6619    1.7481    0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
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 12 13  1  0
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 14 16  1  0
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 17 18  1  0
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 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
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 26 28  1  0
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 31 32  1  0
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 34 35  1  0
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 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
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 41 42  2  0
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  1 47  1  0
  1 48  1  0
  1 49  1  0
  2 50  1  0
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  3 52  1  0
  3 53  1  0
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  4 55  1  0
  5 56  1  0
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 46106  1  0
 46107  1  0
 46108  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  H   UNK     0      39.437  -5.837   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      34.026  -7.839   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.766  -8.567   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.506  -7.839   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      35.286  -8.567   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      30.245  -8.567   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      31.782 -10.022   0.000  0.00  0.00           O+0
HETATM    8  P   UNK     0      36.547  -7.839   0.000  0.00  0.00           P+0
HETATM    9  O   UNK     0      35.819  -6.579   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      37.274  -9.099   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      37.807  -7.111   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      39.067  -7.839   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      40.327  -7.111   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0      33.863 -10.077   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      41.626  -5.967   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      43.115  -6.828   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      41.626  -4.390   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      41.267  -8.386   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      11.574  -7.797   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.907  -8.567   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.241  -7.797   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.575  -8.567   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.908  -7.797   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.242  -7.797   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.576  -8.567   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.909  -7.797   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.243  -8.567   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      23.577  -7.797   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      24.910  -8.567   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      26.244  -7.797   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      27.578  -8.567   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      28.912  -7.797   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      28.912  -6.257   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      13.111 -10.792   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.444 -10.022   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      15.778 -10.792   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      17.112 -10.022   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      18.445 -10.792   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      19.779 -10.792   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      21.113 -10.022   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      22.446 -10.792   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      23.780 -10.022   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      25.114 -10.792   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      26.448 -10.022   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      27.781 -10.792   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      29.115 -10.022   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      30.449 -10.792   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      30.449 -12.332   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2    3    5                                                       
CONECT    3    2    4    7   14                                             
CONECT    4    3    6                                                       
CONECT    5    2    8                                                       
CONECT    6    4   32                                                       
CONECT    7    3   47                                                       
CONECT    8    5    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   15   18    1                                             
CONECT   14    3                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13                                                            
CONECT   19   20                                                            
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31    6   33                                                  
CONECT   33   32                                                            
CONECT   34   35                                                            
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46    7   48                                                  
CONECT   48   47                                                            
MASTER        0    0    0    0    0    0    0    0   48    0   94    0
END

COMPND    HMDB0012342
HETATM    1  C1  UNL     1      13.814   3.124  -0.547  1.00  0.00           C  
HETATM    2  C2  UNL     1      12.277   3.058  -0.625  1.00  0.00           C  
HETATM    3  C3  UNL     1      11.707   3.057   0.783  1.00  0.00           C  
HETATM    4  C4  UNL     1      10.260   2.930   0.831  1.00  0.00           C  
HETATM    5  C5  UNL     1       9.259   3.853   0.404  1.00  0.00           C  
HETATM    6  C6  UNL     1       8.452   3.645  -0.601  1.00  0.00           C  
HETATM    7  C7  UNL     1       8.397   2.506  -1.474  1.00  0.00           C  
HETATM    8  C8  UNL     1       7.136   1.591  -1.281  1.00  0.00           C  
HETATM    9  C9  UNL     1       7.443   0.863   0.007  1.00  0.00           C  
HETATM   10  C10 UNL     1       6.488  -0.033   0.629  1.00  0.00           C  
HETATM   11  C11 UNL     1       5.895  -1.173  -0.100  1.00  0.00           C  
HETATM   12  C12 UNL     1       5.034  -1.946   0.877  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.907  -1.220   1.501  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.912  -0.772   0.438  1.00  0.00           C  
HETATM   15  O1  UNL     1       3.315  -0.049  -0.462  1.00  0.00           O  
HETATM   16  O2  UNL     1       1.634  -1.178   0.495  1.00  0.00           O  
HETATM   17  C15 UNL     1       0.545  -0.903  -0.327  1.00  0.00           C  
HETATM   18  C16 UNL     1      -0.610  -1.761   0.295  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.342  -3.198  -0.333  1.00  0.00           C  
HETATM   20  O3  UNL     1      -1.540  -3.815  -0.347  1.00  0.00           O  
HETATM   21  P1  UNL     1      -1.889  -5.112  -1.208  1.00  0.00           P  
HETATM   22  O4  UNL     1      -2.321  -4.603  -2.644  1.00  0.00           O  
HETATM   23  O5  UNL     1      -3.502  -5.701  -0.667  1.00  0.00           O  
HETATM   24  O6  UNL     1      -1.034  -6.441  -1.425  1.00  0.00           O  
HETATM   25  C18 UNL     1      -0.138  -6.923  -0.470  1.00  0.00           C  
HETATM   26  C19 UNL     1      -0.712  -8.309  -0.206  1.00  0.00           C  
HETATM   27  N1  UNL     1      -1.951  -8.113   0.551  1.00  0.00           N  
HETATM   28  C20 UNL     1       0.077  -9.367   0.261  1.00  0.00           C  
HETATM   29  O7  UNL     1       1.307  -9.554   0.138  1.00  0.00           O  
HETATM   30  O8  UNL     1      -0.604 -10.425   0.985  1.00  0.00           O  
HETATM   31  O9  UNL     1      -1.774  -1.470  -0.344  1.00  0.00           O  
HETATM   32  C21 UNL     1      -2.971  -0.953   0.008  1.00  0.00           C  
HETATM   33  O10 UNL     1      -3.220  -0.527   1.126  1.00  0.00           O  
HETATM   34  C22 UNL     1      -4.001  -0.977  -1.126  1.00  0.00           C  
HETATM   35  C23 UNL     1      -5.119  -0.064  -0.848  1.00  0.00           C  
HETATM   36  C24 UNL     1      -4.646   1.394  -0.943  1.00  0.00           C  
HETATM   37  C25 UNL     1      -5.792   2.285  -0.532  1.00  0.00           C  
HETATM   38  C26 UNL     1      -5.956   2.130   0.982  1.00  0.00           C  
HETATM   39  C27 UNL     1      -7.230   2.719   1.459  1.00  0.00           C  
HETATM   40  C28 UNL     1      -7.529   4.131   1.150  1.00  0.00           C  
HETATM   41  C29 UNL     1      -8.878   4.375   1.684  1.00  0.00           C  
HETATM   42  C30 UNL     1      -9.913   4.592   0.943  1.00  0.00           C  
HETATM   43  C31 UNL     1      -9.892   4.623  -0.511  1.00  0.00           C  
HETATM   44  C32 UNL     1     -10.613   3.518  -1.183  1.00  0.00           C  
HETATM   45  C33 UNL     1     -12.010   3.234  -0.793  1.00  0.00           C  
HETATM   46  C34 UNL     1     -12.136   2.766   0.641  1.00  0.00           C  
HETATM   47  H1  UNL     1      14.072   3.049   0.545  1.00  0.00           H  
HETATM   48  H2  UNL     1      14.177   4.040  -1.015  1.00  0.00           H  
HETATM   49  H3  UNL     1      14.278   2.204  -0.989  1.00  0.00           H  
HETATM   50  H4  UNL     1      11.993   2.125  -1.147  1.00  0.00           H  
HETATM   51  H5  UNL     1      11.881   3.949  -1.157  1.00  0.00           H  
HETATM   52  H6  UNL     1      12.149   2.141   1.305  1.00  0.00           H  
HETATM   53  H7  UNL     1      12.087   3.921   1.370  1.00  0.00           H  
HETATM   54  H8  UNL     1       9.951   2.694   1.965  1.00  0.00           H  
HETATM   55  H9  UNL     1      10.052   1.858   0.445  1.00  0.00           H  
HETATM   56  H10 UNL     1       9.159   4.813   0.983  1.00  0.00           H  
HETATM   57  H11 UNL     1       7.708   4.478  -0.799  1.00  0.00           H  
HETATM   58  H12 UNL     1       9.259   1.796  -1.388  1.00  0.00           H  
HETATM   59  H13 UNL     1       8.427   2.853  -2.520  1.00  0.00           H  
HETATM   60  H14 UNL     1       7.128   0.971  -2.178  1.00  0.00           H  
HETATM   61  H15 UNL     1       6.262   2.229  -1.239  1.00  0.00           H  
HETATM   62  H16 UNL     1       8.465   0.344  -0.149  1.00  0.00           H  
HETATM   63  H17 UNL     1       7.684   1.684   0.738  1.00  0.00           H  
HETATM   64  H18 UNL     1       7.116  -0.558   1.475  1.00  0.00           H  
HETATM   65  H19 UNL     1       5.766   0.560   1.263  1.00  0.00           H  
HETATM   66  H20 UNL     1       6.660  -1.885  -0.470  1.00  0.00           H  
HETATM   67  H21 UNL     1       5.333  -0.872  -1.017  1.00  0.00           H  
HETATM   68  H22 UNL     1       5.714  -2.314   1.709  1.00  0.00           H  
HETATM   69  H23 UNL     1       4.691  -2.894   0.365  1.00  0.00           H  
HETATM   70  H24 UNL     1       4.232  -0.241   1.984  1.00  0.00           H  
HETATM   71  H25 UNL     1       3.380  -1.774   2.294  1.00  0.00           H  
HETATM   72  H26 UNL     1       0.742  -1.347  -1.341  1.00  0.00           H  
HETATM   73  H27 UNL     1       0.256   0.125  -0.500  1.00  0.00           H  
HETATM   74  H28 UNL     1      -0.553  -1.746   1.330  1.00  0.00           H  
HETATM   75  H29 UNL     1       0.238  -3.091  -1.219  1.00  0.00           H  
HETATM   76  H30 UNL     1       0.295  -3.728   0.441  1.00  0.00           H  
HETATM   77  H31 UNL     1      -3.860  -5.076  -0.067  1.00  0.00           H  
HETATM   78  H32 UNL     1       0.011  -6.343   0.400  1.00  0.00           H  
HETATM   79  H33 UNL     1       0.849  -7.112  -0.990  1.00  0.00           H  
HETATM   80  H34 UNL     1      -1.111  -8.677  -1.260  1.00  0.00           H  
HETATM   81  H35 UNL     1      -1.901  -7.431   1.300  1.00  0.00           H  
HETATM   82  H36 UNL     1      -2.768  -8.581   0.278  1.00  0.00           H  
HETATM   83  H37 UNL     1      -1.495 -10.662   0.484  1.00  0.00           H  
HETATM   84  H38 UNL     1      -4.374  -2.044  -1.118  1.00  0.00           H  
HETATM   85  H39 UNL     1      -3.522  -0.852  -2.081  1.00  0.00           H  
HETATM   86  H40 UNL     1      -5.936  -0.203  -1.664  1.00  0.00           H  
HETATM   87  H41 UNL     1      -5.657  -0.302   0.064  1.00  0.00           H  
HETATM   88  H42 UNL     1      -4.407   1.590  -2.030  1.00  0.00           H  
HETATM   89  H43 UNL     1      -3.755   1.512  -0.356  1.00  0.00           H  
HETATM   90  H44 UNL     1      -5.520   3.321  -0.827  1.00  0.00           H  
HETATM   91  H45 UNL     1      -6.716   1.915  -1.043  1.00  0.00           H  
HETATM   92  H46 UNL     1      -5.874   1.108   1.306  1.00  0.00           H  
HETATM   93  H47 UNL     1      -5.119   2.751   1.410  1.00  0.00           H  
HETATM   94  H48 UNL     1      -7.227   2.642   2.598  1.00  0.00           H  
HETATM   95  H49 UNL     1      -8.112   2.046   1.203  1.00  0.00           H  
HETATM   96  H50 UNL     1      -7.307   4.505   0.161  1.00  0.00           H  
HETATM   97  H51 UNL     1      -6.830   4.749   1.830  1.00  0.00           H  
HETATM   98  H52 UNL     1      -8.952   4.371   2.797  1.00  0.00           H  
HETATM   99  H53 UNL     1     -10.886   4.811   1.420  1.00  0.00           H  
HETATM  100  H54 UNL     1      -8.881   4.681  -0.974  1.00  0.00           H  
HETATM  101  H55 UNL     1     -10.386   5.588  -0.902  1.00  0.00           H  
HETATM  102  H56 UNL     1     -10.038   2.554  -1.246  1.00  0.00           H  
HETATM  103  H57 UNL     1     -10.658   3.824  -2.285  1.00  0.00           H  
HETATM  104  H58 UNL     1     -12.716   4.062  -1.006  1.00  0.00           H  
HETATM  105  H59 UNL     1     -12.366   2.371  -1.441  1.00  0.00           H  
HETATM  106  H60 UNL     1     -12.804   3.407   1.201  1.00  0.00           H  
HETATM  107  H61 UNL     1     -11.153   2.535   1.082  1.00  0.00           H  
HETATM  108  H62 UNL     1     -12.662   1.748   0.656  1.00  0.00           H  
CONECT    1    2   47   48   49
CONECT    2    3   50   51
CONECT    3    4   52   53
CONECT    4    5   54   55
CONECT    5    6    6   56
CONECT    6    7   57
CONECT    7    8   58   59
CONECT    8    9   60   61
CONECT    9   10   62   63
CONECT   10   11   64   65
CONECT   11   12   66   67
CONECT   12   13   68   69
CONECT   13   14   70   71
CONECT   14   15   15   16
CONECT   16   17
CONECT   17   18   72   73
CONECT   18   19   31   74
CONECT   19   20   75   76
CONECT   20   21
CONECT   21   22   22   23   24
CONECT   23   77
CONECT   24   25
CONECT   25   26   78   79
CONECT   26   27   28   80
CONECT   27   81   82
CONECT   28   29   29   30
CONECT   30   83
CONECT   31   32
CONECT   32   33   33   34
CONECT   34   35   84   85
CONECT   35   36   86   87
CONECT   36   37   88   89
CONECT   37   38   90   91
CONECT   38   39   92   93
CONECT   39   40   94   95
CONECT   40   41   96   97
CONECT   41   42   42   98
CONECT   42   43   99
CONECT   43   44  100  101
CONECT   44   45  102  103
CONECT   45   46  104  105
CONECT   46  106  107  108
END

HMDB0012342
     RDKit          3D
PS(14:1(9Z)/14:1(9Z))
108107  0  0  0  0  0  0  0  0999 V2000
   13.8138    3.1237   -0.5470 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2767    3.0579   -0.6248 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7069    3.0566    0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2595    2.9305    0.8311 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2593    3.8529    0.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4523    3.6452   -0.6009 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3973    2.5064   -1.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1359    1.5915   -1.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4431    0.8628    0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4883   -0.0327    0.6292 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8951   -1.1734   -0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0339   -1.9460    0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9068   -1.2198    1.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9116   -0.7724    0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3153   -0.0494   -0.4615 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6344   -1.1783    0.4946 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5446   -0.9026   -0.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6105   -1.7614    0.2953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3421   -3.1982   -0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5400   -3.8150   -0.3472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8894   -5.1122   -1.2080 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.3211   -4.6028   -2.6440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5016   -5.7010   -0.6671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0340   -6.4412   -1.4251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1384   -6.9233   -0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7123   -8.3095   -0.2060 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9514   -8.1127    0.5509 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0765   -9.3672    0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3071   -9.5541    0.1379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6043  -10.4246    0.9848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7745   -1.4699   -0.3435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -0.9526    0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2203   -0.5267    1.1263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0008   -0.9775   -1.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1191   -0.0645   -0.8480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6458    1.3936   -0.9427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7920    2.2851   -0.5320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9563    2.1296    0.9821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2303    2.7191    1.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5295    4.1313    1.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8777    4.3749    1.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9133    4.5924    0.9435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8923    4.6234   -0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6135    3.5176   -1.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0105    3.2337   -0.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1360    2.7657    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0718    3.0493    0.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1770    4.0402   -1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.2777    2.2043   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9932    2.1251   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8809    3.9488   -1.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1486    2.1413    1.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0872    3.9210    1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9506    2.6937    1.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0518    1.8583    0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1591    4.8130    0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7083    4.4781   -0.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2590    1.7964   -1.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4266    2.8530   -2.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1283    0.9715   -2.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2624    2.2287   -1.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4645    0.3439   -0.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6839    1.6837    0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1157   -0.5582    1.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7661    0.5598    1.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6597   -1.8849   -0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3332   -0.8717   -1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7144   -2.3139    1.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6907   -2.8935    0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2318   -0.2413    1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3796   -1.7736    2.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7415   -1.3471   -1.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2561    0.1255   -0.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5530   -1.7458    1.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2375   -3.0907   -1.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2952   -3.7276    0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8603   -5.0760   -0.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0109   -6.3428    0.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8495   -7.1119   -0.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1110   -8.6774   -1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9008   -7.4307    1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7682   -8.5806    0.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4945  -10.6619    0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3742   -2.0442   -1.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5218   -0.8523   -2.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9356   -0.2027   -1.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6567   -0.3022    0.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4066    1.5902   -2.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7550    1.5117   -0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5201    3.3212   -0.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7160    1.9149   -1.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8738    1.1081    1.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1189    2.7515    1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2265    2.6418    2.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1117    2.0456    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3066    4.5051    0.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8304    4.7494    1.8298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9516    4.3705    2.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8859    4.8109    1.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8814    4.6805   -0.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3864    5.5877   -0.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0378    2.5541   -1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6585    3.8238   -2.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7164    4.0618   -1.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3658    2.3712   -1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8039    3.4072    1.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1529    2.5352    1.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6619    1.7481    0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 28 30  1  0
 18 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 43 44  1  0
 44 45  1  0
 45 46  1  0
  1 47  1  0
  1 48  1  0
  1 49  1  0
  2 50  1  0
  2 51  1  0
  3 52  1  0
  3 53  1  0
  4 54  1  0
  4 55  1  0
  5 56  1  0
  6 57  1  0
  7 58  1  0
  7 59  1  0
  8 60  1  0
  8 61  1  0
  9 62  1  0
  9 63  1  0
 10 64  1  0
 10 65  1  0
 11 66  1  0
 11 67  1  0
 12 68  1  0
 12 69  1  0
 13 70  1  0
 13 71  1  0
 17 72  1  0
 17 73  1  0
 18 74  1  1
 19 75  1  0
 19 76  1  0
 23 77  1  0
 25 78  1  0
 25 79  1  0
 26 80  1  6
 27 81  1  0
 27 82  1  0
 30 83  1  0
 34 84  1  0
 34 85  1  0
 35 86  1  0
 35 87  1  0
 36 88  1  0
 36 89  1  0
 37 90  1  0
 37 91  1  0
 38 92  1  0
 38 93  1  0
 39 94  1  0
 39 95  1  0
 40 96  1  0
 40 97  1  0
 41 98  1  0
 42 99  1  0
 43100  1  0
 43101  1  0
 44102  1  0
 44103  1  0
 45104  1  0
 45105  1  0
 46106  1  0
 46107  1  0
 46108  1  0
M  END

Synonyms

Value	Source
1,2-Dimyristoleoyl-rac-glycero-3-phosphoserine	HMDB
Phosphatidylserine(14:1/14:1)	HMDB
Phosphatidylserine(14:1n5/14:1n5)	HMDB
Phosphatidylserine(14:1W5/14:1W5)	HMDB
Phosphatidylserine(28:2)	HMDB
PS(14:1/14:1)	HMDB
PS(14:1N5/14:1N5)	HMDB
PS(14:1W5/14:1W5)	HMDB
PS(28:2)	HMDB
pSer(14:1/14:1)	HMDB
pSer(14:1n5/14:1n5)	HMDB
pSer(14:1W5/14:1W5)	HMDB
pSer(28:2)	HMDB
1,2-Di(9Z-tetradecenoyl)-rac-glycero-3-phosphoserine	HMDB
PS(14:1(9Z)/14:1(9Z))	Lipid Annotator

Molecular Formula

C₃₄H₆₂NO₁₀P

Average Mass

675.8305

Monoisotopic Mass

675.411133721

IUPAC Name

(2S)-2-amino-3-({[(2R)-2,3-bis[(9Z)-tetradec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)propanoic acid

Traditional Name

(2S)-2-amino-3-{[(2R)-2,3-bis[(9Z)-tetradec-9-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}propanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCC)OC(=O)CCCCCCC\C=C/CCCC)C(O)=O

InChI Identifier

InChI=1S/C34H62NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-32(36)42-27-30(28-43-46(40,41)44-29-31(35)34(38)39)45-33(37)26-24-22-20-18-16-14-12-10-8-6-4-2/h9-12,30-31H,3-8,13-29,35H2,1-2H3,(H,38,39)(H,40,41)/b11-9-,12-10-/t30-,31+/m1/s1

InChI Key

BPFJDFFAZFFCBH-QPBIGPORSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylserines. These are glycerophosphoserines in which two fatty acids are bonded to the glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoserines

Direct Parent

Phosphatidylserines

Alternative Parents

Substituents

Diacyl-glycerol-3-phosphoserine
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Tricarboxylic acid or derivatives
Phosphoethanolamine
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Amino acid
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Carbonyl group
Organic oxide
Primary amine
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Diacylglycerophosphoserines (LMGP03010919 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0003 g/L	ALOGPS
logP	3.44	ALOGPS
logP	6.99	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	1.47	ChemAxon
pKa (Strongest Basic)	9.38	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	171.68 Å²	ChemAxon
Rotatable Bond Count	34	ChemAxon
Refractivity	180.66 m³·mol⁻¹	ChemAxon
Polarizability	76.94 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-18	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000920000-6613d814991675f212dc	2016-09-19	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000009000-f2840c6edb1d5b372031	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0000019000-5f495bf957b982c381c8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01y9-0167096000-96838934f72212758f4c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000109000-60545931fb9edc58d8b8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002f-0010914000-faffdbc738fd75072742	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0010911000-f4a890904471cd2dc58e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ot-0000009000-a38bbe95841941b46489	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0000009000-70016144bb9c684c75b3	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0090114000-3e4c8b26be6971dd0948	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001q-0000999000-cc353d7f87d6e44ea856	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000y-0900999000-7791de48e3ca3d1bcb43	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000y-0900999000-7791de48e3ca3d1bcb43	2021-09-23	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (retained)	2025-10-24	368.8
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	92.6
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	911.1
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	805.4
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	1130.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	201.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	3921.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	536.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	322.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	749.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	223.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	191.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	268.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	8.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	294.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	760.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	558.1
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1990.8
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	2197.3

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_1	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](N)C(=O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	standard non polar	2025-10-24	1848.33
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_2	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N)C(=O)O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	standard non polar	2025-10-24	2031.87
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_3	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O)OC(=O)CCCCCCC/C=C\CCCC	standard non polar	2025-10-24	1801.98
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_4	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	standard non polar	2025-10-24	2540.13
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_5	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	standard non polar	2025-10-24	2478.47
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_6	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	standard non polar	2025-10-24	1834.14
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_7	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	standard non polar	2025-10-24	1655.97
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_8	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	standard non polar	2025-10-24	1685.15
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_9	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	standard non polar	2025-10-24	2259.92
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_10	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	standard non polar	2025-10-24	2828.0
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_1	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](N)C(=O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	standard polar	2025-10-24	2172.15
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_2	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N)C(=O)O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	standard polar	2025-10-24	1324.62
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_3	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O)OC(=O)CCCCCCC/C=C\CCCC	standard polar	2025-10-24	2268.04
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_4	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	standard polar	2025-10-24	3139.0
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_5	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	standard polar	2025-10-24	2403.21
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_6	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	standard polar	2025-10-24	1677.46
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_7	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	standard polar	2025-10-24	2608.85
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_8	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	standard polar	2025-10-24	1990.0
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_9	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	standard polar	2025-10-24	2429.01
Gas Chromatography	PS(14:1(9Z)/14:1(9Z))_TMS_10	CCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	standard polar	2025-10-24	1727.9

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

All Tissues
Brain
Heart
Kidney
Liver

Tissue Locations

All Tissues
Brain
Heart
Kidney
Liver

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191737	Group 10 secretory phospholipase A2	Unknown	O15496	Homo sapiens
MMDBp0191895	Diacylglycerol kinase gamma	Unknown	P49619	Homo sapiens
MMDBp0191903	Diacylglycerol kinase alpha	Unknown	P23743	Homo sapiens
MMDBp0191904	Diacylglycerol kinase delta	Unknown	Q16760	Homo sapiens
MMDBp0191908	Diacylglycerol kinase beta	Unknown	Q9Y6T7	Homo sapiens
MMDBp0192779	Protein kinase C alpha type	Unknown	P17252	Homo sapiens
MMDBp0192939	Probable phospholipid-transporting ATPase IA	Unknown	Q9Y2Q0	Homo sapiens
MMDBp0193358	Phospholipid scramblase 1	Unknown	O15162	Homo sapiens
MMDBp0193448	Phosphatidylserine synthase 1	Enzyme	P48651	Homo sapiens
MMDBp0193462	Scavenger receptor class B member 1	Enzyme	Q8WTV0	Homo sapiens
MMDBp0193468	C-X-C motif chemokine 16	Unknown	Q9H2A7	Homo sapiens
MMDBp0193473	Phosphatidylserine decarboxylase proenzyme	Enzyme	Q9UG56	Homo sapiens
MMDBp0193622	Bifunctional arginine demethylase and lysyl-hydroxylase JMJD6	Unknown	Q6NYC1	Homo sapiens
MMDBp0193745	Phosphatidylserine synthase 2	Enzyme	Q9BVG9	Homo sapiens
MMDBp0193807	2-acylglycerol O-acyltransferase 2	Enzyme	Q3SYC2	Homo sapiens
MMDBp0193826	Phosphatidylinositol-4-phosphate 3-kinase C2 domain-containing subunit alpha	Unknown	O00443	Homo sapiens
MMDBp0193888	Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2	Enzyme	O15357	Homo sapiens
MMDBp0193977	1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-3	Unknown	Q8N3E9	Homo sapiens
MMDBp0194037	Sphingomyelin phosphodiesterase 3	Unknown	Q9NY59	Homo sapiens
MMDBp0194090	Phospholipid scramblase 2	Unknown	Q9NRY7	Homo sapiens
MMDBp0194091	Phospholipid scramblase 3	Unknown	Q9NRY6	Homo sapiens
MMDBp0194092	Phospholipid scramblase 4	Unknown	Q9NRQ2	Homo sapiens
MMDBp0194093	Phospholipid scramblase family member 5	Unknown	A0PG75	Homo sapiens
MMDBp0194102	Phospholipase A1 member A	Enzyme	Q53H76	Homo sapiens
MMDBp0194103	Serum deprivation-response protein	Unknown	O95810	Homo sapiens
MMDBp0194236	Transcriptional regulator ATRX	Unknown	P46100	Homo sapiens
MMDBp0194392	Copine-1	Unknown	Q99829	Homo sapiens
MMDBp0194396	Copine-6	Unknown	O95741	Homo sapiens
MMDBp0195099	Cdc42-interacting protein 4	Unknown	Q15642	Homo sapiens
MMDBp0195159	Formin-binding protein 1-like	Unknown	Q5T0N5	Homo sapiens
MMDBp0195167	Formin-binding protein 1	Unknown	Q96RU3	Homo sapiens
MMDBp0195538	Sphingomyelin phosphodiesterase 4	Unknown	Q9NXE4	Homo sapiens
MMDBp0196314	Serine incorporator 1	Unknown	Q9NRX5	Homo sapiens
MMDBp0196463	Protein kinase C delta-binding protein	Enzyme	Q969G5	Homo sapiens
MMDBp0196504	Annexin A9	Unknown	O76027	Homo sapiens
MMDBp0196505	Phosphatidylserine receptor transcript variant 2	Unknown	B2WTI4	Homo sapiens
MMDBp0196506	Serine incorporator 5	Unknown	Q86VE9	Homo sapiens
MMDBp0196507	Adseverin	Unknown	Q9Y6U3	Homo sapiens
MMDBp0196508	Serine incorporator 4	Unknown	A6NH21	Homo sapiens
MMDBp0196509	Phosphatidylserine receptor transcript variant 1	Unknown	B2WTI3	Homo sapiens
MMDBp0196666	Lactadherin	Enzyme	Q08431	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

This table shows at most 5 pathways. For the full list of associated pathways:

See All Associated Bacterial Pathways

Name	SMPDB/PathBank	Species
Phosphatidylcholine Biosynthesis PC(14:1(9Z)/14:1(9Z))
Phospholipid Biosynthesis CL(14:1(9Z)/14:1(9Z)/14:1(11Z)/18:0)
Phospholipid Biosynthesis CL(14:1(9Z)/14:1(9Z)/14:1(11Z)/18:1(11Z))
Phospholipid Biosynthesis CL(14:1(9Z)/14:1(9Z)/14:1(11Z)/18:1(9Z))
Phospholipid Biosynthesis CL(14:1(9Z)/14:1(9Z)/14:1(11Z)/20:0)

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human All tissues	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Brain	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Heart	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0012342

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028961

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52926026

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. doi: 10.1016/0092-8674(95)90409-3. [PubMed:7834746 ]
van Engeland M, Nieland LJ, Ramaekers FC, Schutte B, Reutelingsperger CP: Annexin V-affinity assay: a review on an apoptosis detection system based on phosphatidylserine exposure. Cytometry. 1998 Jan 1;31(1):1-9. doi: 10.1002/(sici)1097-0320(19980101)31:1<1::aid-cyto1>3.0.co;2-r. [PubMed:9450519 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Vance JE, Tasseva G: Formation and function of phosphatidylserine and phosphatidylethanolamine in mammalian cells. Biochim Biophys Acta. 2013 Mar;1831(3):543-54. doi: 10.1016/j.bbalip.2012.08.016. Epub 2012 Aug 29. [PubMed:22960354 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
Jean E. Vance (2008). Thematic Review Series: Glycerolipids. Phosphatidylserine and phosphatidylethanolamine in mammalian cells: two metabolically related aminophospholipids. The Journal of Lipid Research, 49, 1377-1387..

Showing metabocard for PS(14:1(9Z)/14:1(9Z)) (MMDBc0047244)

MOL for #<Metabolite:0x00007f9abcecea88>

3D MOL for #<Metabolite:0x00007f9abcecea88>

3D SDF for #<Metabolite:0x00007f9abcecea88>

3D-SDF for #<Metabolite:0x00007f9abcecea88>

PDB for #<Metabolite:0x00007f9abcecea88>

3D PDB for #<Metabolite:0x00007f9abcecea88>

SMILES for #<Metabolite:0x00007f9abcecea88>

INCHI for #<Metabolite:0x00007f9abcecea88>

Structure for #<Metabolite:0x00007f9abcecea88>

3D Structure for #<Metabolite:0x00007f9abcecea88>