MiMeDB: Showing metabocard for Cytidine 5'-monophosphate-N-acetylneuraminic acid (MMDBc0047922)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:15:36 UTC

Update Date

2024-04-30 20:32:37 UTC

Metabolite ID

MMDBc0047922

Metabolite Identification

Common Name

Cytidine 5'-monophosphate-N-acetylneuraminic acid

Description

Cytidine 5'-monophosphate-N-acetylneuraminic acid (CMP-Neu5Ac), also known as CMP-N-acetyl-β-neuraminic acid, belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. CMP-Neu5Ac is an extremely weak basic (essentially neutral) compound (based on its pKa). CMP-Neu5Ac donates N-acetylneuraminic acid to the terminal sugar of a ganglioside or glycoprotein.

Structure

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


  Mrv1652304202019252D          

 42 44  0  0  1  0            999 V2000
   -0.7145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4290    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001   -1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433    0.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8251    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    0.4126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4288    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5722    0.4127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    1.2374    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.6199   -1.0431    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2874   -0.5582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8749   -1.8277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9548   -1.0431    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6999   -1.8277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3900   -2.4952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7394   -0.7882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1848   -2.4952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9109    0.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3525   -1.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6956    0.2738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2979    0.5709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1372   -1.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3087   -0.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0933   -0.0233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8353   -0.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -2.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 17  1  1  0  0  0
  1  2  1  0  0  0  0
  2 18  1  1  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  8  1  6  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  5  1  0  0  0  0
  6  7  1  0  0  0  0
  6 20  1  1  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  1  0  0  0
 12 14  1  0  0  0  0
 12 15  1  6  0  0  0
 14 16  1  0  0  0  0
 18 19  1  0  0  0  0
 19 41  2  0  0  0  0
 19 42  1  0  0  0  0
 20 23  1  0  0  0  0
 23 21  2  0  0  0  0
 23 22  1  0  0  0  0
 23 39  1  0  0  0  0
 24 40  1  1  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  6  0  0  0
 27 30  1  1  0  0  0
 27 28  1  0  0  0  0
 28 31  1  6  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  2  0  0  0  0
 33 36  2  0  0  0  0
 34 37  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 40 39  1  0  0  0  0
M  END

HMDB0001176
     RDKit          3D
Cytidine 5'-monophosphate-N-acetylneuraminic acid
 72 74  0  0  0  0  0  0  0  0999 V2000
   -7.9558    1.8617    0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9911    1.5620   -0.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5083    1.6806   -1.8940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7169    1.2142   -0.4525 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4442    0.8668   -0.1461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2991    1.6939   -0.7201 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2967    2.9823   -0.1972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9843    1.0058   -0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8235   -0.1922    0.1272 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9737   -1.1444   -0.4487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5554   -0.6406   -0.8013 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.6472    0.7409   -1.4051 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1721   -1.6958   -2.0127 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6666   -0.7070    0.4605 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9552   -0.9427    0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9510   -1.0012    1.1480 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1886   -1.2590    0.5867 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0803   -0.2891    0.9477 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1331   -0.0922   -0.0080 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4289    0.0328    0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4614    0.2204   -0.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1740    0.2861   -1.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2066    0.4841   -2.8535 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8886    0.1630   -2.2454 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9199   -0.0185   -1.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7451   -0.1269   -1.7452 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2160    0.9667    1.1402 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8498    1.8828    1.9499 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0435    0.2992    1.8826 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4554    0.0898    3.1881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3183    0.1623    1.4623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204   -0.4174    2.0117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8910    1.1621    2.2314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0128   -0.9038    0.3355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0326   -0.5691   -0.5010 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1881   -1.5219   -0.4516 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1567   -1.0490   -1.3273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7637   -1.7087    0.9293 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7329   -2.2091    1.7247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8450   -2.7627    0.8546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9130   -2.2778    0.0621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8712    1.0474    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9543    1.9666    0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5842    2.8173    0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4033    1.1014   -1.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2440    0.9317    0.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5958    1.8334   -1.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2128    3.6737   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327    1.7880   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6450    0.7466   -1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8223   -1.2303   -2.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9557   -1.8132   -0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484   -0.0665   -0.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6652   -1.8337    1.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5531   -0.5002    1.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6735   -0.0181    1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4961    0.3212   -0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0063    0.5414   -3.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1820    0.5699   -2.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8676    1.3565    0.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2813    2.6740    2.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1254    0.8811    1.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2411   -0.8368    3.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629    2.1084    2.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7198   -0.5207   -1.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8403   -2.4850   -0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9387   -1.1929   -2.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1676   -0.7564    1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1685   -2.8376    1.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4129   -3.6319    0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1703   -3.1485    1.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9644   -1.3150    0.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  6
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 18 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
  9 31  1  0
 31 32  2  0
 31 33  1  0
  9 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 35  5  1  0
 29 16  1  0
 25 19  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  4 45  1  0
  5 46  1  1
  6 47  1  6
  7 48  1  0
  8 49  1  0
  8 50  1  0
 13 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  1
 18 55  1  1
 20 56  1  0
 21 57  1  0
 23 58  1  0
 23 59  1  0
 27 60  1  6
 28 61  1  0
 29 62  1  1
 30 63  1  0
 33 64  1  0
 35 65  1  6
 36 66  1  6
 37 67  1  0
 38 68  1  1
 39 69  1  0
 40 70  1  0
 40 71  1  0
 41 72  1  0
M  END


  Mrv1652304202019252D          

 42 44  0  0  1  0            999 V2000
   -0.7145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4290    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001   -1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433    0.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8251    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    0.4126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4288    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5722    0.4127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    1.2374    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.6199   -1.0431    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2874   -0.5582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8749   -1.8277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9548   -1.0431    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6999   -1.8277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3900   -2.4952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7394   -0.7882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1848   -2.4952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9109    0.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3525   -1.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6956    0.2738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2979    0.5709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1372   -1.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3087   -0.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0933   -0.0233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8353   -0.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -2.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 17  1  1  0  0  0
  1  2  1  0  0  0  0
  2 18  1  1  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  8  1  6  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  5  1  0  0  0  0
  6  7  1  0  0  0  0
  6 20  1  1  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  1  0  0  0
 12 14  1  0  0  0  0
 12 15  1  6  0  0  0
 14 16  1  0  0  0  0
 18 19  1  0  0  0  0
 19 41  2  0  0  0  0
 19 42  1  0  0  0  0
 20 23  1  0  0  0  0
 23 21  2  0  0  0  0
 23 22  1  0  0  0  0
 23 39  1  0  0  0  0
 24 40  1  1  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  6  0  0  0
 27 30  1  1  0  0  0
 27 28  1  0  0  0  0
 28 31  1  6  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  2  0  0  0  0
 33 36  2  0  0  0  0
 34 37  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 40 39  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047922

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(O[C@](C[C@H](O)[C@H]1NC(C)=O)(OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O)C(O)=O)[C@H](O)[C@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C20H31N4O16P/c1-7(26)22-12-8(27)4-20(18(32)33,39-16(12)13(29)9(28)5-25)40-41(35,36)37-6-10-14(30)15(31)17(38-10)24-3-2-11(21)23-19(24)34/h2-3,8-10,12-17,25,27-31H,4-6H2,1H3,(H,22,26)(H,32,33)(H,35,36)(H2,21,23,34)/t8-,9+,10+,12+,13+,14+,15+,16+,17+,20+/m0/s1

> <INCHI_KEY>
TXCIAUNLDRJGJZ-BILDWYJOSA-N

> <FORMULA>
C20H31N4O16P

> <MOLECULAR_WEIGHT>
614.4511

> <EXACT_MASS>
614.147267476

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.80805383702998

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4S,5R,6R)-2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

> <ALOGPS_LOGP>
-2.70

> <JCHEM_LOGP>
-5.740562122522781

> <ALOGPS_LOGS>
-1.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.95934847850933

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4845894703438178

> <JCHEM_PKA_STRONGEST_BASIC>
-0.21961406785414483

> <JCHEM_POLAR_SURFACE_AREA>
320.69

> <JCHEM_REFRACTIVITY>
125.42009999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.63e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cmp-sialic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001176
     RDKit          3D
Cytidine 5'-monophosphate-N-acetylneuraminic acid
 72 74  0  0  0  0  0  0  0  0999 V2000
   -7.9558    1.8617    0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9911    1.5620   -0.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5083    1.6806   -1.8940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7169    1.2142   -0.4525 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4442    0.8668   -0.1461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2991    1.6939   -0.7201 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2967    2.9823   -0.1972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9843    1.0058   -0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8235   -0.1922    0.1272 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9737   -1.1444   -0.4487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5554   -0.6406   -0.8013 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.6472    0.7409   -1.4051 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1721   -1.6958   -2.0127 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6666   -0.7070    0.4605 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9552   -0.9427    0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9510   -1.0012    1.1480 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1886   -1.2590    0.5867 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0803   -0.2891    0.9477 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1331   -0.0922   -0.0080 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4289    0.0328    0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4614    0.2204   -0.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1740    0.2861   -1.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2066    0.4841   -2.8535 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8886    0.1630   -2.2454 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9199   -0.0185   -1.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7451   -0.1269   -1.7452 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2160    0.9667    1.1402 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8498    1.8828    1.9499 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0435    0.2992    1.8826 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4554    0.0898    3.1881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3183    0.1623    1.4623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204   -0.4174    2.0117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8910    1.1621    2.2314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0128   -0.9038    0.3355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0326   -0.5691   -0.5010 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1881   -1.5219   -0.4516 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1567   -1.0490   -1.3273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7637   -1.7087    0.9293 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7329   -2.2091    1.7247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8450   -2.7627    0.8546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9130   -2.2778    0.0621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8712    1.0474    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9543    1.9666    0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5842    2.8173    0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4033    1.1014   -1.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2440    0.9317    0.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5958    1.8334   -1.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2128    3.6737   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327    1.7880   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6450    0.7466   -1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8223   -1.2303   -2.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9557   -1.8132   -0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484   -0.0665   -0.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6652   -1.8337    1.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5531   -0.5002    1.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6735   -0.0181    1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4961    0.3212   -0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0063    0.5414   -3.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1820    0.5699   -2.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8676    1.3565    0.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2813    2.6740    2.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1254    0.8811    1.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2411   -0.8368    3.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629    2.1084    2.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7198   -0.5207   -1.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8403   -2.4850   -0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9387   -1.1929   -2.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1676   -0.7564    1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1685   -2.8376    1.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4129   -3.6319    0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1703   -3.1485    1.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9644   -1.3150    0.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  6
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 18 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
  9 31  1  0
 31 32  2  0
 31 33  1  0
  9 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 35  5  1  0
 29 16  1  0
 25 19  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  4 45  1  0
  5 46  1  1
  6 47  1  6
  7 48  1  0
  8 49  1  0
  8 50  1  0
 13 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  1
 18 55  1  1
 20 56  1  0
 21 57  1  0
 23 58  1  0
 23 59  1  0
 27 60  1  6
 28 61  1  0
 29 62  1  1
 30 63  1  0
 33 64  1  0
 35 65  1  6
 36 66  1  6
 37 67  1  0
 38 68  1  1
 39 69  1  0
 40 70  1  0
 40 71  1  0
 41 72  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667   3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -6.668   0.770   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0      -1.334   2.310   0.000  0.00  0.00           H+0
HETATM   18  N   UNK     0      -2.667  -1.540   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   23  P   UNK     0       2.667  -1.540   0.000  0.00  0.00           P+0
HETATM   24  C   UNK     0       6.757  -1.947   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.003  -1.042   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.233  -3.412   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.249  -1.947   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.773  -3.412   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.328  -4.658   0.000  0.00  0.00           O+0
HETATM   30  N   UNK     0      10.714  -1.471   0.000  0.00  0.00           N+0
HETATM   31  O   UNK     0       9.678  -4.658   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      11.034   0.035   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.858  -2.502   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      12.498   0.511   0.000  0.00  0.00           N+0
HETATM   35  O   UNK     0       9.889   1.066   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      13.323  -2.026   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.643  -0.519   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      15.107  -0.043   0.000  0.00  0.00           N+0
HETATM   39  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.293  -1.471   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
CONECT    1   11   17    2    3                                             
CONECT    2    1   18    4                                                  
CONECT    3    1    6                                                       
CONECT    4    2    8    5                                                  
CONECT    5    4    6                                                       
CONECT    6    3    5    7   20                                             
CONECT    7    6    9   10                                                  
CONECT    8    4                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    1   12   13                                                  
CONECT   12   11   14   15                                                  
CONECT   13   11                                                            
CONECT   14   12   16                                                       
CONECT   15   12                                                            
CONECT   16   14                                                            
CONECT   17    1                                                            
CONECT   18    2   19                                                       
CONECT   19   18   41   42                                                  
CONECT   20    6   23                                                       
CONECT   21   23                                                            
CONECT   22   23                                                            
CONECT   23   20   21   22   39                                             
CONECT   24   40   25   26                                                  
CONECT   25   24   27                                                       
CONECT   26   24   28   29                                                  
CONECT   27   25   30   28                                                  
CONECT   28   26   27   31                                                  
CONECT   29   26                                                            
CONECT   30   27   32   33                                                  
CONECT   31   28                                                            
CONECT   32   30   34   35                                                  
CONECT   33   30   36                                                       
CONECT   34   32   37                                                       
CONECT   35   32                                                            
CONECT   36   33   37                                                       
CONECT   37   34   36   38                                                  
CONECT   38   37                                                            
CONECT   39   23   40                                                       
CONECT   40   24   39                                                       
CONECT   41   19                                                            
CONECT   42   19                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   88    0
END

COMPND    HMDB0001176
HETATM    1  C1  UNL     1      -7.956   1.862   0.419  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.991   1.562  -0.759  1.00  0.00           C  
HETATM    3  O1  UNL     1      -7.508   1.681  -1.894  1.00  0.00           O  
HETATM    4  N1  UNL     1      -5.717   1.214  -0.452  1.00  0.00           N  
HETATM    5  C3  UNL     1      -4.444   0.867  -0.146  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.299   1.694  -0.720  1.00  0.00           C  
HETATM    7  O2  UNL     1      -3.297   2.982  -0.197  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.984   1.006  -0.720  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.824  -0.192   0.127  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.974  -1.144  -0.449  1.00  0.00           O  
HETATM   11  P1  UNL     1       0.555  -0.641  -0.801  1.00  0.00           P  
HETATM   12  O4  UNL     1       0.647   0.741  -1.405  1.00  0.00           O  
HETATM   13  O5  UNL     1       1.172  -1.696  -2.013  1.00  0.00           O  
HETATM   14  O6  UNL     1       1.667  -0.707   0.460  1.00  0.00           O  
HETATM   15  C7  UNL     1       2.955  -0.943   0.030  1.00  0.00           C  
HETATM   16  C8  UNL     1       3.951  -1.001   1.148  1.00  0.00           C  
HETATM   17  O7  UNL     1       5.189  -1.259   0.587  1.00  0.00           O  
HETATM   18  C9  UNL     1       6.080  -0.289   0.948  1.00  0.00           C  
HETATM   19  N2  UNL     1       7.133  -0.092  -0.008  1.00  0.00           N  
HETATM   20  C10 UNL     1       8.429   0.033   0.368  1.00  0.00           C  
HETATM   21  C11 UNL     1       9.461   0.220  -0.527  1.00  0.00           C  
HETATM   22  C12 UNL     1       9.174   0.286  -1.872  1.00  0.00           C  
HETATM   23  N3  UNL     1      10.207   0.484  -2.853  1.00  0.00           N  
HETATM   24  N4  UNL     1       7.889   0.163  -2.245  1.00  0.00           N  
HETATM   25  C13 UNL     1       6.920  -0.019  -1.332  1.00  0.00           C  
HETATM   26  O8  UNL     1       5.745  -0.127  -1.745  1.00  0.00           O  
HETATM   27  C14 UNL     1       5.216   0.967   1.140  1.00  0.00           C  
HETATM   28  O9  UNL     1       5.850   1.883   1.950  1.00  0.00           O  
HETATM   29  C15 UNL     1       4.044   0.299   1.883  1.00  0.00           C  
HETATM   30  O10 UNL     1       4.455   0.090   3.188  1.00  0.00           O  
HETATM   31  C16 UNL     1      -1.318   0.162   1.462  1.00  0.00           C  
HETATM   32  O11 UNL     1      -0.320  -0.417   2.012  1.00  0.00           O  
HETATM   33  O12 UNL     1      -1.891   1.162   2.231  1.00  0.00           O  
HETATM   34  O13 UNL     1      -3.013  -0.904   0.335  1.00  0.00           O  
HETATM   35  C17 UNL     1      -4.033  -0.569  -0.501  1.00  0.00           C  
HETATM   36  C18 UNL     1      -5.188  -1.522  -0.452  1.00  0.00           C  
HETATM   37  O14 UNL     1      -6.157  -1.049  -1.327  1.00  0.00           O  
HETATM   38  C19 UNL     1      -5.764  -1.709   0.929  1.00  0.00           C  
HETATM   39  O15 UNL     1      -4.733  -2.209   1.725  1.00  0.00           O  
HETATM   40  C20 UNL     1      -6.845  -2.763   0.855  1.00  0.00           C  
HETATM   41  O16 UNL     1      -7.913  -2.278   0.062  1.00  0.00           O  
HETATM   42  H1  UNL     1      -7.871   1.047   1.167  1.00  0.00           H  
HETATM   43  H2  UNL     1      -8.954   1.967   0.017  1.00  0.00           H  
HETATM   44  H3  UNL     1      -7.584   2.817   0.848  1.00  0.00           H  
HETATM   45  H4  UNL     1      -5.403   1.101  -1.789  1.00  0.00           H  
HETATM   46  H5  UNL     1      -4.244   0.932   0.989  1.00  0.00           H  
HETATM   47  H6  UNL     1      -3.596   1.833  -1.805  1.00  0.00           H  
HETATM   48  H7  UNL     1      -3.213   3.674  -0.906  1.00  0.00           H  
HETATM   49  H8  UNL     1      -1.233   1.788  -0.395  1.00  0.00           H  
HETATM   50  H9  UNL     1      -1.645   0.747  -1.767  1.00  0.00           H  
HETATM   51  H10 UNL     1       1.822  -1.230  -2.569  1.00  0.00           H  
HETATM   52  H11 UNL     1       2.956  -1.813  -0.638  1.00  0.00           H  
HETATM   53  H12 UNL     1       3.248  -0.066  -0.596  1.00  0.00           H  
HETATM   54  H13 UNL     1       3.665  -1.834   1.804  1.00  0.00           H  
HETATM   55  H14 UNL     1       6.553  -0.500   1.947  1.00  0.00           H  
HETATM   56  H15 UNL     1       8.674  -0.018   1.441  1.00  0.00           H  
HETATM   57  H16 UNL     1      10.496   0.321  -0.226  1.00  0.00           H  
HETATM   58  H17 UNL     1      10.006   0.541  -3.861  1.00  0.00           H  
HETATM   59  H18 UNL     1      11.182   0.570  -2.518  1.00  0.00           H  
HETATM   60  H19 UNL     1       4.868   1.356   0.169  1.00  0.00           H  
HETATM   61  H20 UNL     1       5.281   2.674   2.023  1.00  0.00           H  
HETATM   62  H21 UNL     1       3.125   0.881   1.815  1.00  0.00           H  
HETATM   63  H22 UNL     1       4.241  -0.837   3.492  1.00  0.00           H  
HETATM   64  H23 UNL     1      -1.563   2.108   2.146  1.00  0.00           H  
HETATM   65  H24 UNL     1      -3.720  -0.521  -1.576  1.00  0.00           H  
HETATM   66  H25 UNL     1      -4.840  -2.485  -0.865  1.00  0.00           H  
HETATM   67  H26 UNL     1      -5.939  -1.193  -2.264  1.00  0.00           H  
HETATM   68  H27 UNL     1      -6.168  -0.756   1.333  1.00  0.00           H  
HETATM   69  H28 UNL     1      -4.169  -2.838   1.237  1.00  0.00           H  
HETATM   70  H29 UNL     1      -6.413  -3.632   0.289  1.00  0.00           H  
HETATM   71  H30 UNL     1      -7.170  -3.149   1.823  1.00  0.00           H  
HETATM   72  H31 UNL     1      -7.964  -1.315   0.226  1.00  0.00           H  
CONECT    1    2   42   43   44
CONECT    2    3    3    4
CONECT    4    5   45
CONECT    5    6   35   46
CONECT    6    7    8   47
CONECT    7   48
CONECT    8    9   49   50
CONECT    9   10   31   34
CONECT   10   11
CONECT   11   12   12   13   14
CONECT   13   51
CONECT   14   15
CONECT   15   16   52   53
CONECT   16   17   29   54
CONECT   17   18
CONECT   18   19   27   55
CONECT   19   20   25
CONECT   20   21   21   56
CONECT   21   22   57
CONECT   22   23   24   24
CONECT   23   58   59
CONECT   24   25
CONECT   25   26   26
CONECT   27   28   29   60
CONECT   28   61
CONECT   29   30   62
CONECT   30   63
CONECT   31   32   32   33
CONECT   33   64
CONECT   34   35
CONECT   35   36   65
CONECT   36   37   38   66
CONECT   37   67
CONECT   38   39   40   68
CONECT   39   69
CONECT   40   41   70   71
CONECT   41   72
END

HMDB0001176
     RDKit          3D
Cytidine 5'-monophosphate-N-acetylneuraminic acid
 72 74  0  0  0  0  0  0  0  0999 V2000
   -7.9558    1.8617    0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9911    1.5620   -0.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5083    1.6806   -1.8940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7169    1.2142   -0.4525 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4442    0.8668   -0.1461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2991    1.6939   -0.7201 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2967    2.9823   -0.1972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9843    1.0058   -0.7195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8235   -0.1922    0.1272 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9737   -1.1444   -0.4487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5554   -0.6406   -0.8013 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.6472    0.7409   -1.4051 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1721   -1.6958   -2.0127 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6666   -0.7070    0.4605 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9552   -0.9427    0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9510   -1.0012    1.1480 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1886   -1.2590    0.5867 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0803   -0.2891    0.9477 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1331   -0.0922   -0.0080 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4289    0.0328    0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4614    0.2204   -0.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1740    0.2861   -1.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2066    0.4841   -2.8535 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8886    0.1630   -2.2454 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9199   -0.0185   -1.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7451   -0.1269   -1.7452 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2160    0.9667    1.1402 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8498    1.8828    1.9499 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0435    0.2992    1.8826 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4554    0.0898    3.1881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3183    0.1623    1.4623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204   -0.4174    2.0117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8910    1.1621    2.2314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0128   -0.9038    0.3355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0326   -0.5691   -0.5010 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1881   -1.5219   -0.4516 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1567   -1.0490   -1.3273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7637   -1.7087    0.9293 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7329   -2.2091    1.7247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8450   -2.7627    0.8546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9130   -2.2778    0.0621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8712    1.0474    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9543    1.9666    0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5842    2.8173    0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4033    1.1014   -1.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2440    0.9317    0.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5958    1.8334   -1.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2128    3.6737   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327    1.7880   -0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6450    0.7466   -1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8223   -1.2303   -2.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9557   -1.8132   -0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484   -0.0665   -0.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6652   -1.8337    1.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5531   -0.5002    1.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6735   -0.0181    1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4961    0.3212   -0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0063    0.5414   -3.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1820    0.5699   -2.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8676    1.3565    0.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2813    2.6740    2.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1254    0.8811    1.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2411   -0.8368    3.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629    2.1084    2.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7198   -0.5207   -1.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8403   -2.4850   -0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9387   -1.1929   -2.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1676   -0.7564    1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1685   -2.8376    1.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4129   -3.6319    0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1703   -3.1485    1.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9644   -1.3150    0.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  6
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 18 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
  9 31  1  0
 31 32  2  0
 31 33  1  0
  9 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 35  5  1  0
 29 16  1  0
 25 19  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  4 45  1  0
  5 46  1  1
  6 47  1  6
  7 48  1  0
  8 49  1  0
  8 50  1  0
 13 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  1
 18 55  1  1
 20 56  1  0
 21 57  1  0
 23 58  1  0
 23 59  1  0
 27 60  1  6
 28 61  1  0
 29 62  1  1
 30 63  1  0
 33 64  1  0
 35 65  1  6
 36 66  1  6
 37 67  1  0
 38 68  1  1
 39 69  1  0
 40 70  1  0
 40 71  1  0
 41 72  1  0
M  END

Synonyms

Value	Source
CMP Acetylneuraminic acid	ChEBI
CMP-beta-Neu5ac	ChEBI
CMP-N-Acetylneuraminate	ChEBI
CMP-Nana	ChEBI
CMP-Neu5ac	ChEBI
CMP-NeuNAc	ChEBI
CMP-Sialic acid	ChEBI
Cytidine monophosphate N-acetylneuraminic acid	ChEBI
CYTIDINE-5'-monophosphATE-5-N-acetylneuraminIC ACID	ChEBI
Cytidine-5'-monophospho-N-acetylneuraminic acid	ChEBI
Cytidine-5'-monophosphono-N-acetylneuraminic acid	ChEBI
CMP-N-Acetyl-beta-neuraminate	Kegg
CMP Acetylneuraminate	Generator
CMP-b-Neu5ac	Generator
CMP-Β-neu5ac	Generator
CMP-N-Acetylneuraminic acid	Generator
CMP-Sialate	Generator
Cytidine monophosphate N-acetylneuraminate	Generator
Cytidine monophosphoric acid N-acetylneuraminic acid	Generator
CYTIDINE-5'-monophosphate-5-N-acetylneuraminate	Generator
CYTIDINE-5'-monophosphoric acid-5-N-acetylneuraminic acid	Generator
Cytidine-5'-monophospho-N-acetylneuraminate	Generator
Cytidine-5'-monophosphono-N-acetylneuraminate	Generator
CMP-N-Acetyl-b-neuraminate	Generator
CMP-N-Acetyl-b-neuraminic acid	Generator
CMP-N-Acetyl-beta-neuraminic acid	Generator
CMP-N-Acetyl-β-neuraminate	Generator
CMP-N-Acetyl-β-neuraminic acid	Generator
Cytidine 5'-monophosphate-N-acetylneuraminate	Generator
Cytidine 5'-monophosphoric acid-N-acetylneuraminic acid	Generator
CMP-N-Acylneuraminate	HMDB
Cytidine 5'-monophosphate N-acetylneuraminic acid	HMDB
Acetylneuraminic acid, CMP	HMDB
Acid, CMP acetylneuraminic	HMDB
Acid, CMP-sialic	HMDB
CMP Sialic acid	HMDB
Cytidine monophosphate N acetylneuraminic acid	HMDB
CMP-NeuAc	HMDB
Cytidine 5'-monophosphic acid-N-acetylneuraminic acid	HMDB
Cytidine 5'-monophospho-N-acetylneuraminate	HMDB
Cytidine 5'-monophospho-N-acetylneuraminic acid	HMDB
Cytidine 5’-monophosphate-N-acetylneuraminate	HMDB
Cytidine 5’-monophosphate-N-acetylneuraminic acid	HMDB
Cytidine 5’-monophosphic acid-N-acetylneuraminic acid	HMDB
Cytidine 5’-monophospho-N-acetylneuraminate	HMDB
Cytidine 5’-monophospho-N-acetylneuraminic acid	HMDB
Cytidine monophosphic acid N-acetylneuraminic acid	HMDB
Cytidine 5'-monophosphate-N-acetylneuraminic acid	HMDB

Molecular Formula

C₂₀H₃₁N₄O₁₆P

Average Mass

614.4511

Monoisotopic Mass

614.147267476

IUPAC Name

(2R,4S,5R,6R)-2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

Traditional Name

cmp-sialic acid

CAS Registry Number

3063-71-6

SMILES

[H][C@]1(O[C@](C[C@H](O)[C@H]1NC(C)=O)(OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O)C(O)=O)[C@H](O)[C@H](O)CO

InChI Identifier

InChI=1S/C20H31N4O16P/c1-7(26)22-12-8(27)4-20(18(32)33,39-16(12)13(29)9(28)5-25)40-41(35,36)37-6-10-14(30)15(31)17(38-10)24-3-2-11(21)23-19(24)34/h2-3,8-10,12-17,25,27-31H,4-6H2,1H3,(H,22,26)(H,32,33)(H,35,36)(H2,21,23,34)/t8-,9+,10+,12+,13+,14+,15+,16+,17+,20+/m0/s1

InChI Key

TXCIAUNLDRJGJZ-BILDWYJOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine nucleotide sugars

Direct Parent

Pyrimidine nucleotide sugars

Alternative Parents

Substituents

Pyrimidine nucleotide sugar
Pyrimidine ribonucleoside monophosphate
N-acylneuraminic acid
N-acylneuraminic acid or derivatives
Neuraminic acid
Pentose phosphate
Pentose-5-phosphate
C-glucuronide
C-glycosyl compound
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Aminopyrimidine
Pyrimidone
Dialkyl phosphate
Hydropyrimidine
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Pyran
Pyrimidine
Imidolactam
Alkyl phosphate
Tetrahydrofuran
Acetamide
Heteroaromatic compound
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Amino acid
Amino acid or derivatives
Polyol
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Primary amine
Alcohol
Primary alcohol
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

CMP-N-acyl-beta-neuraminic acid (CHEBI:16556 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	36.3 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-5.7	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.48	ChemAxon
pKa (Strongest Basic)	-0.22	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	320.69 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	125.42 m³·mol⁻¹	ChemAxon
Polarizability	53.81 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Golgi apparatus
Nucleus

Biospecimen Locations

Feces
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191878	CMP-N-acetylneuraminate-beta-1,4-galactoside alpha-2,3-sialyltransferase	Enzyme	Q11203	Homo sapiens
MMDBp0191941	Alpha-N-acetylneuraminide alpha-2,8-sialyltransferase	Enzyme	Q92185	Homo sapiens
MMDBp0192066	N-acylneuraminate cytidylyltransferase	Enzyme	Q8NFW8	Homo sapiens
MMDBp0192393	Lactosylceramide alpha-2,3-sialyltransferase	Enzyme	Q9UNP4	Homo sapiens
MMDBp0192394	Type 2 lactosamine alpha-2,3-sialyltransferase	Enzyme	Q9Y274	Homo sapiens
MMDBp0193454	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	Enzyme	Q11201	Homo sapiens
MMDBp0193825	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 4	Enzyme	Q11206	Homo sapiens
MMDBp0196030	Alpha-N-acetyl-neuraminyl-2,3-beta-galactosyl-1,3-N-acetyl-galactosaminide alpha-2,6-sialyltransferase	Enzyme	Q9H4F1	Homo sapiens
MMDBp0196968	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 2	Unknown	Q16842
MMDBp0196969	Alpha-N-acetylgalactosaminide alpha-2,6-sialyltransferase 1	Unknown	Q9NSC7
MMDBp0196970	Alpha-N-acetylgalactosaminide alpha-2,6-sialyltransferase 2	Unknown	Q9UJ37
MMDBp0196971	Alpha-N-acetylgalactosaminide alpha-2,6-sialyltransferase 3	Unknown	Q8NDV1
MMDBp0196972	Beta-galactoside alpha-2,6-sialyltransferase 1	Unknown	P15907
MMDBp0196973	Beta-galactoside alpha-2,6-sialyltransferase 2	Unknown	Q96JF0

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
Bacteria/Eubacteria	Firmicutes	75	Human feces; Human pleural fluid plaque; Human ; Human stool	Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	47	Human feces; Human sputum; Pig ; Human ; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	17	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human ; Human mucosa; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	50	Human feces; Human ; Human stool; Human saliva	Metabolic reconstruction
Bacteria	Proteobacteria	1	Human feces; Human sputum; Pig ; Human ; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria	Actinobacteria	3	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human ; Human mucosa; Human saliva	Metabolic reconstruction
Bacteria	Firmicutes	8	Human feces; Human pleural fluid plaque; Human ; Human stool	Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	8	Human feces	Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0001176

DrugBank ID

DB02485

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022466

KNApSAcK ID

Not Available

Chemspider ID

395082

KEGG Compound ID

C00128

BioCyc ID

Not Available

BiGG ID

33954

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

448209

PDB ID

Not Available

ChEBI ID

16556

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Hurh S, Kang B, Choi I, Cho B, Lee EM, Kim H, Kim YJ, Chung YS, Jeong JC, Hwang JI, Kim JY, Lee BC, Surh CD, Yang J, Ahn C: Human antibody reactivity against xenogeneic N-glycolylneuraminic acid and galactose-alpha-1,3-galactose antigen. Xenotransplantation. 2016 Jul;23(4):279-92. doi: 10.1111/xen.12239. Epub 2016 Jul 4. [PubMed:27373998 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Cytidine 5'-monophosphate-N-acetylneuraminic acid (MMDBc0047922)

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