MiMeDB: Showing metabocard for PI(12:0/22:1(9Z)) (MMDBc0047068)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:07:17 UTC

Update Date

2022-09-01 01:41:04 UTC

Metabolite ID

MMDBc0047068

Metabolite Identification

Common Name

PI(12:0/22:1(9Z))

Description

PI(12:0/22:1(9Z))is a phosphatidylinositol. Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols 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 18 and 20 carbons are the most common.PI(12:0/22:1(9Z)), in particular, consists of one dodecanoyl chain to the C-1 atom, and one 9Z-docosenoyl to the C-2 atom. In most organisms, the stereochemical form of the last is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes. 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. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol.

Structure

MOL SDF PDB SMILES InChI

PI(12:0/22:1(9Z))
  Mrv1652306231617122D          

 58 58  0  0  1  0            999 V2000
   -2.6340    0.3607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3442    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0543    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2236   -0.3496    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0444   -0.3496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9236    0.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2134    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7241    0.3394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0236    0.6438    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3853    0.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0236    1.3916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4847    0.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1813    1.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043   -0.1685    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8093    0.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1162   -0.1685    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7899    1.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3891    0.7974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8053    1.2227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9631    1.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0243    0.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4745    0.8368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7645    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7645    1.5409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4787    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1928    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9070    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6211    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3353    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0494    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7635    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4776    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1918    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9060    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6201    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7884   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7884   -1.5407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5026   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2167   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9308   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6450   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3591   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0733   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7874   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5016   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3266   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0407   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7548   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4689   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1831   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8972   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6114   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3255   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.0397   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.7538   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.4679   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.1821   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.8962   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  4  1  1  0  0  0
  2  3  1  0  0  0  0
  3 23  1  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  7  9  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 12 20  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 14  8  1  1  0  0  0
 15 19  1  0  0  0  0
 16 17  1  0  0  0  0
 16 15  1  0  0  0  0
 16 21  1  1  0  0  0
 17 22  1  0  0  0  0
 23 24  2  0  0  0  0
 23 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 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 36  5  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  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  2  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
M  END

PI(12:0/22:1(9Z))
  Mrv1652306231617122D          

 58 58  0  0  1  0            999 V2000
   -2.6340    0.3607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3442    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0543    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2236   -0.3496    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0444   -0.3496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9236    0.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2134    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7241    0.3394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0236    0.6438    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3853    0.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0236    1.3916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4847    0.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1813    1.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043   -0.1685    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8093    0.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1162   -0.1685    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7899    1.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3891    0.7974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8053    1.2227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9631    1.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0243    0.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4745    0.8368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7645    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7645    1.5409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4787    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1928    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9070    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6211    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3353    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0494    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7635    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4776    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1918    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9060    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6201    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7884   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7884   -1.5407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5026   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2167   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9308   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6450   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3591   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0733   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7874   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5016   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3266   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0407   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7548   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4689   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1831   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8972   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6114   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3255   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.0397   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.7538   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.4679   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.1821   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.8962   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  4  1  1  0  0  0
  2  3  1  0  0  0  0
  3 23  1  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  7  9  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 12 20  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 14  8  1  1  0  0  0
 15 19  1  0  0  0  0
 16 17  1  0  0  0  0
 16 15  1  0  0  0  0
 16 21  1  1  0  0  0
 17 22  1  0  0  0  0
 23 24  2  0  0  0  0
 23 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 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 36  5  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  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  2  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047068

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](COC(=O)CCCCCCCCCCC)(COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](O)C1O)OC(=O)CCCCCCC\C=C/CCCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C43H81O13P/c1-3-5-7-9-11-13-14-15-16-17-18-19-20-21-22-24-26-28-30-32-37(45)55-35(33-53-36(44)31-29-27-25-23-12-10-8-6-4-2)34-54-57(51,52)56-43-41(49)39(47)38(46)40(48)42(43)50/h19-20,35,38-43,46-50H,3-18,21-34H2,1-2H3,(H,51,52)/b20-19-/t35-,38?,39-,40?,41?,42?,43-/m1/s1

> <INCHI_KEY>
KTDYKOPDRWFIOD-NCBQTMLFSA-N

> <FORMULA>
C43H81O13P

> <MOLECULAR_WEIGHT>
837.082

> <EXACT_MASS>
836.541479666

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
138

> <JCHEM_AVERAGE_POLARIZABILITY>
98.91329653845588

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-2-[(9Z)-docos-9-enoyloxy]-3-(dodecanoyloxy)propoxy]({[(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid

> <ALOGPS_LOGP>
7.30

> <JCHEM_LOGP>
9.521271563333336

> <ALOGPS_LOGS>
-5.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.360530531715522

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8332552462032856

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6458130204247565

> <JCHEM_POLAR_SURFACE_AREA>
209.50999999999996

> <JCHEM_REFRACTIVITY>
220.88639999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
39

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.90e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(9Z)-docos-9-enoyloxy]-3-(dodecanoyloxy)propoxy([(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-JUN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PI(12:0/22:1(9Z))                                 
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JUN-16         0                                  
HETATM    1  C   UNK     0      -4.917   0.673   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.242   1.436   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -7.568   0.673   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0      -4.151  -0.653   0.000  0.00  0.00           H+0
HETATM    5  O   UNK     0      -5.683  -0.653   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.591   1.439   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.265   0.673   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.352   0.634   0.000  0.00  0.00           O+0
HETATM    9  P   UNK     0      -0.044   1.202   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0      -0.719   0.031   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.044   2.598   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.505   1.235   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.072   1.885   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.808  -0.315   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.244   0.342   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.684  -0.315   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.941   1.885   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.593   1.488   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.237   2.282   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.398   2.342   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.379   0.241   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.219   1.562   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -8.894   1.436   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -8.894   2.876   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0     -10.227   0.665   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -11.560   1.436   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -12.893   0.665   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -14.226   1.436   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -15.559   0.665   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -16.892   1.436   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -18.225   0.665   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -19.558   1.436   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -20.891   0.665   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -22.224   1.436   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -23.557   0.665   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -7.072  -1.436   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -7.072  -2.876   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -8.405  -0.665   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -9.738  -1.436   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -11.071  -0.665   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -12.404  -1.436   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -13.737  -0.665   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -15.070  -1.436   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -16.403  -0.665   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -17.736  -1.436   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -19.276  -1.436   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -20.609  -0.665   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -21.942  -1.436   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -23.275  -0.665   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -24.609  -1.436   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -25.942  -0.665   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     -27.275  -1.436   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0     -28.608  -0.665   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0     -29.941  -1.436   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0     -31.274  -0.665   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0     -32.607  -1.436   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0     -33.940  -0.665   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0     -35.273  -1.436   0.000  0.00  0.00           C+0
CONECT    1    2    5    4    6                                             
CONECT    2    1    3                                                       
CONECT    3    2   23                                                       
CONECT    4    1                                                            
CONECT    5    1   36                                                       
CONECT    6    1    7                                                       
CONECT    7    6    9                                                       
CONECT    8    9   14                                                       
CONECT    9    7    8   10   11                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12   13   17   20                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15    8                                                  
CONECT   15   14   19   16                                                  
CONECT   16   17   15   21                                                  
CONECT   17   12   16   22                                                  
CONECT   18   13                                                            
CONECT   19   15                                                            
CONECT   20   12                                                            
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23    3   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   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   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36    5   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   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   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  116    0
END

Synonyms

Value	Source
[(2R)-2-[(9Z)-Docos-9-enoyloxy]-3-(dodecanoyloxy)propoxy]({[(1S,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinate	Generator

Molecular Formula

C₄₃H₈₁O₁₃P

Average Mass

837.082

Monoisotopic Mass

836.541479666

IUPAC Name

[(2R)-2-[(9Z)-docos-9-enoyloxy]-3-(dodecanoyloxy)propoxy]({[(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid

Traditional Name

(2R)-2-[(9Z)-docos-9-enoyloxy]-3-(dodecanoyloxy)propoxy([(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCCCCCCCCCC)(COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](O)C1O)OC(=O)CCCCCCC\C=C/CCCCCCCCCCCC

InChI Identifier

InChI=1S/C43H81O13P/c1-3-5-7-9-11-13-14-15-16-17-18-19-20-21-22-24-26-28-30-32-37(45)55-35(33-53-36(44)31-29-27-25-23-12-10-8-6-4-2)34-54-57(51,52)56-43-41(49)39(47)38(46)40(48)42(43)50/h19-20,35,38-43,46-50H,3-18,21-34H2,1-2H3,(H,51,52)/b20-19-/t35-,38?,39-,40?,41?,42?,43-/m1/s1

InChI Key

KTDYKOPDRWFIOD-NCBQTMLFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylinositols. These are glycerophosphoinositols where the glycerol is esterified with two fatty acids.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoinositols

Direct Parent

Phosphatidylinositols

Alternative Parents

Substituents

Diacylglycerophosphoinositol
Inositol phosphate
Dialkyl phosphate
Fatty acid ester
Cyclohexanol
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Dicarboxylic acid or derivatives
Cyclitol or derivatives
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00089 g/L	ALOGPS
logP	7.3	ALOGPS
logP	9.52	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	1.83	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	209.51 Å²	ChemAxon
Rotatable Bond Count	39	ChemAxon
Refractivity	220.89 m³·mol⁻¹	ChemAxon
Polarizability	98.91 Å³	ChemAxon
Number of Rings	1	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0frj-0609367000-bc685c340e0d34da277a	2016-09-19	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

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	Activity	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Rattray JB, Schibeci A, Kidby DK: Lipids of yeasts. Bacteriol Rev. 1975 Sep;39(3):197-231. doi: 10.1128/br.39.3.197-231.1975. [PubMed:240350 ]

Showing metabocard for PI(12:0/22:1(9Z)) (MMDBc0047068)

MOL for #<Metabolite:0x00007fca69eb5c18>

3D MOL for #<Metabolite:0x00007fca69eb5c18>

3D SDF for #<Metabolite:0x00007fca69eb5c18>

3D-SDF for #<Metabolite:0x00007fca69eb5c18>

PDB for #<Metabolite:0x00007fca69eb5c18>

3D PDB for #<Metabolite:0x00007fca69eb5c18>

SMILES for #<Metabolite:0x00007fca69eb5c18>

INCHI for #<Metabolite:0x00007fca69eb5c18>

Structure for #<Metabolite:0x00007fca69eb5c18>

3D Structure for #<Metabolite:0x00007fca69eb5c18>