MiMeDB: Showing metabocard for Guanosine diphosphate mannose (MMDBc0029575)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:32:52 UTC

Update Date

2024-04-30 19:38:13 UTC

Metabolite ID

MMDBc0029575

Metabolite Identification

Common Name

Guanosine diphosphate mannose

Description

GDP-mannose is a nucleoside diphosphate sugar that is important in the production of fucosylated oligosaccharides. GDP-mannose is transformed to GDP-fucose via three enzymatic reactions carried out by two proteins, GDP-mannose 4,6-dehydratase (GMD) and a second enzyme, GDP-keto-6-deoxymannose 3,5-epimerase, 4-reductase. GDP-mannose 4,6-dehydratase (EC 4.2.1.47) catalyzes the chemical reaction: GDP-mannose <--> GDP-4-dehydro-6-deoxy-D-mannose + H2O. The epimerase converts the GDP-4-dehydro-6-deoxy-D-mannose to GDP-fucose. (PMID: 12651883 ). GDP-mannose is also synthesized from mannose 1-phosphate via the enzyme ATP-mannose-1-phosphate-guanyltransferase and GTP.

Structure

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


  Mrv1652309042000182D          

 39 42  0  0  1  0            999 V2000
    3.7694    1.4268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9784    1.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7656   -0.2119    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2538    2.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9784    2.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2593    1.2564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0843    0.2801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5158   -0.9878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7731    2.7665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2593    2.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5441    1.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4221   -0.2006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6908   -0.9878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0041   -1.6501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5441    2.5091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2556    3.7467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8288    1.2716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6387    0.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2177   -1.6576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9234   -0.3557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0984   -0.3557    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228   -0.3557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0909   -1.2678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1060    0.4655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5478   -0.3557    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3691   -0.3595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5554   -1.2073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5402    0.4655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0843   -0.7683    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7997   -0.3595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0843   -1.5895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5149   -0.7683    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7997   -2.0058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3691   -2.0058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5149   -1.5895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2189   -0.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7997   -2.8271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2189   -2.0058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8508   -0.8893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  1  1  1  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  6  0  0  0
 10 15  1  0  0  0  0
 10 16  2  0  0  0  0
 11 17  1  0  0  0  0
 12 18  1  1  0  0  0
 13 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  2  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  2  0  0  0  0
 29 26  1  6  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  1  0  0  0
 32 35  1  0  0  0  0
 32 36  1  1  0  0  0
 33 37  1  1  0  0  0
 35 38  1  6  0  0  0
 36 39  1  0  0  0  0
  5  9  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 33 35  1  0  0  0  0
M  END

HMDB0001163
     RDKit          3D
Guanosine diphosphate mannose
 64 67  0  0  0  0  0  0  0  0999 V2000
    7.3990    4.1261    0.0313 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3519    2.8567    0.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4716    1.9250    0.2478 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4051    0.7139    0.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2692    0.4509    1.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9868   -0.8224    2.2559 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929   -1.2921    1.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6227   -0.3621    0.5919 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6077   -0.3998   -0.4424 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4020    0.1533   -0.0327 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5636   -0.1426   -1.1091 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1184    0.1157   -0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7304   -0.6750    0.2887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8684   -0.4524    0.7139 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.8839    0.0903    2.1458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6260    0.7290   -0.2391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7700   -1.8666    0.6941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7671   -1.9635   -0.6699 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.2214   -3.3828   -0.8829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7997   -1.5424   -2.0118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0095   -0.8715   -0.5606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1431   -1.3567    0.0819 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2836   -0.5470    1.2306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5036    0.7438    0.7524 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9452    1.7943    1.6779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5097    1.7412    2.9419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9925    0.8941    0.5474 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3020    1.8380   -0.4279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4951   -0.4741    0.0692 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8680   -1.1898    1.1940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3963   -1.1881   -0.7216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9532   -2.4029   -1.1280 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8001   -1.6229   -1.2985 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6432   -1.9691   -2.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2486   -1.7990   -0.8247 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0472   -2.2940   -1.8759 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1652    1.4048    2.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9543    1.1789    3.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2085    2.6049    1.6877 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5550    4.7676    0.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2291    4.4899   -0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5730   -2.2740    1.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9926    0.1037   -1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8890    0.4483   -1.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5236   -0.1018   -1.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9787    1.1982   -0.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0384    1.0093   -0.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0709   -0.6666   -2.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0198   -2.4092    0.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0321    0.9067   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8426    1.6834    1.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1744    2.7975    1.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3402    2.2828    2.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4929    1.1851    1.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7767    1.6881   -1.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3600   -0.3851   -0.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5678   -2.1301    1.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2056   -0.5627   -1.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4334   -3.1787   -0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0988   -2.1579   -0.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7950   -2.4782   -2.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3023   -2.5310   -0.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8903   -1.7865   -2.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8775    3.3573    1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  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
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 11 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
  5 37  1  0
 37 38  2  0
 37 39  1  0
 39  2  1  0
  8  4  1  0
 35  9  1  0
 31 22  1  0
  1 40  1  0
  1 41  1  0
  7 42  1  0
  9 43  1  6
 11 44  1  6
 12 45  1  0
 12 46  1  0
 16 47  1  0
 20 48  1  0
 22 49  1  1
 24 50  1  6
 25 51  1  0
 25 52  1  0
 26 53  1  0
 27 54  1  1
 28 55  1  0
 29 56  1  6
 30 57  1  0
 31 58  1  6
 32 59  1  0
 33 60  1  1
 34 61  1  0
 35 62  1  1
 36 63  1  0
 39 64  1  0
M  END


  Mrv1652309042000182D          

 39 42  0  0  1  0            999 V2000
    3.7694    1.4268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9784    1.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7656   -0.2119    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2538    2.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9784    2.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2593    1.2564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0843    0.2801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5158   -0.9878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7731    2.7665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2593    2.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5441    1.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4221   -0.2006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6908   -0.9878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0041   -1.6501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5441    2.5091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2556    3.7467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8288    1.2716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6387    0.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2177   -1.6576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9234   -0.3557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0984   -0.3557    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228   -0.3557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0909   -1.2678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1060    0.4655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5478   -0.3557    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3691   -0.3595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5554   -1.2073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5402    0.4655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0843   -0.7683    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7997   -0.3595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0843   -1.5895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5149   -0.7683    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7997   -2.0058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3691   -2.0058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5149   -1.5895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2189   -0.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7997   -2.8271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2189   -2.0058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8508   -0.8893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  1  1  1  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  6  0  0  0
 10 15  1  0  0  0  0
 10 16  2  0  0  0  0
 11 17  1  0  0  0  0
 12 18  1  1  0  0  0
 13 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  2  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  2  0  0  0  0
 29 26  1  6  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  1  0  0  0
 32 35  1  0  0  0  0
 32 36  1  1  0  0  0
 33 37  1  1  0  0  0
 35 38  1  6  0  0  0
 36 39  1  0  0  0  0
  5  9  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029575

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C16H25N5O16P2/c17-16-19-12-6(13(28)20-16)18-3-21(12)14-10(26)8(24)5(34-14)2-33-38(29,30)37-39(31,32)36-15-11(27)9(25)7(23)4(1-22)35-15/h3-5,7-11,14-15,22-27H,1-2H2,(H,29,30)(H,31,32)(H3,17,19,20,28)/t4-,5-,7-,8-,9+,10-,11+,14-,15-/m1/s1

> <INCHI_KEY>
MVMSCBBUIHUTGJ-GDJBGNAASA-N

> <FORMULA>
C16H25N5O16P2

> <MOLECULAR_WEIGHT>
605.3411

> <EXACT_MASS>
605.077152801

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.721178469097254

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

> <ALOGPS_LOGP>
-1.76

> <JCHEM_LOGP>
-5.287584132999999

> <ALOGPS_LOGS>
-1.89

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.176324364365109

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7325998238285534

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6484093801081894

> <JCHEM_POLAR_SURFACE_AREA>
327.43

> <JCHEM_REFRACTIVITY>
118.51129999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
guanosine diphosphomannose

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001163
     RDKit          3D
Guanosine diphosphate mannose
 64 67  0  0  0  0  0  0  0  0999 V2000
    7.3990    4.1261    0.0313 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3519    2.8567    0.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4716    1.9250    0.2478 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4051    0.7139    0.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2692    0.4509    1.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9868   -0.8224    2.2559 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929   -1.2921    1.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6227   -0.3621    0.5919 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6077   -0.3998   -0.4424 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4020    0.1533   -0.0327 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5636   -0.1426   -1.1091 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1184    0.1157   -0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7304   -0.6750    0.2887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8684   -0.4524    0.7139 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.8839    0.0903    2.1458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6260    0.7290   -0.2391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7700   -1.8666    0.6941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7671   -1.9635   -0.6699 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.2214   -3.3828   -0.8829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7997   -1.5424   -2.0118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0095   -0.8715   -0.5606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1431   -1.3567    0.0819 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2836   -0.5470    1.2306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5036    0.7438    0.7524 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9452    1.7943    1.6779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5097    1.7412    2.9419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9925    0.8941    0.5474 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3020    1.8380   -0.4279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4951   -0.4741    0.0692 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8680   -1.1898    1.1940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3963   -1.1881   -0.7216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9532   -2.4029   -1.1280 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8001   -1.6229   -1.2985 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6432   -1.9691   -2.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2486   -1.7990   -0.8247 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0472   -2.2940   -1.8759 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1652    1.4048    2.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9543    1.1789    3.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2085    2.6049    1.6877 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5550    4.7676    0.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2291    4.4899   -0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5730   -2.2740    1.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9926    0.1037   -1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8890    0.4483   -1.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5236   -0.1018   -1.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9787    1.1982   -0.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0384    1.0093   -0.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0709   -0.6666   -2.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0198   -2.4092    0.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0321    0.9067   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8426    1.6834    1.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1744    2.7975    1.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3402    2.2828    2.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4929    1.1851    1.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7767    1.6881   -1.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3600   -0.3851   -0.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5678   -2.1301    1.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2056   -0.5627   -1.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4334   -3.1787   -0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0988   -2.1579   -0.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7950   -2.4782   -2.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3023   -2.5310   -0.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8903   -1.7865   -2.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8775    3.3573    1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  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
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 11 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
  5 37  1  0
 37 38  2  0
 37 39  1  0
 39  2  1  0
  8  4  1  0
 35  9  1  0
 31 22  1  0
  1 40  1  0
  1 41  1  0
  7 42  1  0
  9 43  1  6
 11 44  1  6
 12 45  1  0
 12 46  1  0
 16 47  1  0
 20 48  1  0
 22 49  1  1
 24 50  1  6
 25 51  1  0
 25 52  1  0
 26 53  1  0
 27 54  1  1
 28 55  1  0
 29 56  1  6
 30 57  1  0
 31 58  1  6
 32 59  1  0
 33 60  1  1
 34 61  1  0
 35 62  1  1
 36 63  1  0
 39 64  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  N   UNK     0       7.036   2.663   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       5.560   3.137   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.029  -0.396   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.940   3.900   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.560   4.684   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       4.217   2.345   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       5.757   0.523   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.563  -1.844   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       7.043   5.164   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       4.217   5.454   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.882   3.137   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.521  -0.374   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.023  -1.844   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.474  -3.080   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       2.882   4.684   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       4.210   6.994   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       1.547   2.374   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       3.059   0.092   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.140  -3.094   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.724  -0.664   0.000  0.00  0.00           O+0
HETATM   21  P   UNK     0       0.184  -0.664   0.000  0.00  0.00           P+0
HETATM   22  O   UNK     0      -1.349  -0.664   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.170  -2.367   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.198   0.869   0.000  0.00  0.00           O+0
HETATM   25  P   UNK     0      -2.889  -0.664   0.000  0.00  0.00           P+0
HETATM   26  O   UNK     0      -4.422  -0.671   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -2.903  -2.254   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.875   0.869   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -5.757  -1.434   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -7.093  -0.671   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.757  -2.967   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.428  -1.434   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -7.093  -3.744   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.422  -3.744   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -8.428  -2.967   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -9.742  -0.671   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -7.093  -5.277   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -9.742  -3.744   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0     -10.921  -1.660   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10    9                                                  
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    3   13   14                                                  
CONECT    9    4    5                                                       
CONECT   10    5   15   16                                                  
CONECT   11    6   17   15                                                  
CONECT   12    7   18   13                                                  
CONECT   13    8   19   12                                                  
CONECT   14    8                                                            
CONECT   15   10   11                                                       
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   12   20                                                       
CONECT   19   13                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21   25                                                       
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25   22   26   27   28                                             
CONECT   26   25   29                                                       
CONECT   27   25                                                            
CONECT   28   25                                                            
CONECT   29   26   30   31                                                  
CONECT   30   29   32                                                       
CONECT   31   29   33   34                                                  
CONECT   32   30   35   36                                                  
CONECT   33   31   37   35                                                  
CONECT   34   31                                                            
CONECT   35   32   38   33                                                  
CONECT   36   32   39                                                       
CONECT   37   33                                                            
CONECT   38   35                                                            
CONECT   39   36                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

COMPND    HMDB0001163
HETATM    1  N1  UNL     1       7.399   4.126   0.031  1.00  0.00           N  
HETATM    2  C1  UNL     1       7.352   2.857   0.663  1.00  0.00           C  
HETATM    3  N2  UNL     1       6.472   1.925   0.248  1.00  0.00           N  
HETATM    4  C2  UNL     1       6.405   0.714   0.828  1.00  0.00           C  
HETATM    5  C3  UNL     1       7.269   0.451   1.867  1.00  0.00           C  
HETATM    6  N3  UNL     1       6.987  -0.822   2.256  1.00  0.00           N  
HETATM    7  C4  UNL     1       5.993  -1.292   1.475  1.00  0.00           C  
HETATM    8  N4  UNL     1       5.623  -0.362   0.592  1.00  0.00           N  
HETATM    9  C5  UNL     1       4.608  -0.400  -0.442  1.00  0.00           C  
HETATM   10  O1  UNL     1       3.402   0.153  -0.033  1.00  0.00           O  
HETATM   11  C6  UNL     1       2.564  -0.143  -1.109  1.00  0.00           C  
HETATM   12  C7  UNL     1       1.118   0.116  -0.791  1.00  0.00           C  
HETATM   13  O2  UNL     1       0.730  -0.675   0.289  1.00  0.00           O  
HETATM   14  P1  UNL     1      -0.868  -0.452   0.714  1.00  0.00           P  
HETATM   15  O3  UNL     1      -0.884   0.090   2.146  1.00  0.00           O  
HETATM   16  O4  UNL     1      -1.626   0.729  -0.239  1.00  0.00           O  
HETATM   17  O5  UNL     1      -1.770  -1.867   0.694  1.00  0.00           O  
HETATM   18  P2  UNL     1      -2.767  -1.964  -0.670  1.00  0.00           P  
HETATM   19  O6  UNL     1      -3.221  -3.383  -0.883  1.00  0.00           O  
HETATM   20  O7  UNL     1      -1.800  -1.542  -2.012  1.00  0.00           O  
HETATM   21  O8  UNL     1      -4.009  -0.871  -0.561  1.00  0.00           O  
HETATM   22  C8  UNL     1      -5.143  -1.357   0.082  1.00  0.00           C  
HETATM   23  O9  UNL     1      -5.284  -0.547   1.231  1.00  0.00           O  
HETATM   24  C9  UNL     1      -5.504   0.744   0.752  1.00  0.00           C  
HETATM   25  C10 UNL     1      -4.945   1.794   1.678  1.00  0.00           C  
HETATM   26  O10 UNL     1      -5.510   1.741   2.942  1.00  0.00           O  
HETATM   27  C11 UNL     1      -6.993   0.894   0.547  1.00  0.00           C  
HETATM   28  O11 UNL     1      -7.302   1.838  -0.428  1.00  0.00           O  
HETATM   29  C12 UNL     1      -7.495  -0.474   0.069  1.00  0.00           C  
HETATM   30  O12 UNL     1      -7.868  -1.190   1.194  1.00  0.00           O  
HETATM   31  C13 UNL     1      -6.396  -1.188  -0.722  1.00  0.00           C  
HETATM   32  O13 UNL     1      -6.953  -2.403  -1.128  1.00  0.00           O  
HETATM   33  C14 UNL     1       2.800  -1.623  -1.298  1.00  0.00           C  
HETATM   34  O14 UNL     1       2.643  -1.969  -2.619  1.00  0.00           O  
HETATM   35  C15 UNL     1       4.249  -1.799  -0.825  1.00  0.00           C  
HETATM   36  O15 UNL     1       5.047  -2.294  -1.876  1.00  0.00           O  
HETATM   37  C16 UNL     1       8.165   1.405   2.286  1.00  0.00           C  
HETATM   38  O16 UNL     1       8.954   1.179   3.227  1.00  0.00           O  
HETATM   39  N5  UNL     1       8.208   2.605   1.688  1.00  0.00           N  
HETATM   40  H1  UNL     1       6.555   4.768   0.068  1.00  0.00           H  
HETATM   41  H2  UNL     1       8.229   4.490  -0.484  1.00  0.00           H  
HETATM   42  H3  UNL     1       5.573  -2.274   1.565  1.00  0.00           H  
HETATM   43  H4  UNL     1       4.993   0.104  -1.373  1.00  0.00           H  
HETATM   44  H5  UNL     1       2.889   0.448  -1.981  1.00  0.00           H  
HETATM   45  H6  UNL     1       0.524  -0.102  -1.689  1.00  0.00           H  
HETATM   46  H7  UNL     1       0.979   1.198  -0.573  1.00  0.00           H  
HETATM   47  H8  UNL     1      -1.038   1.009  -0.977  1.00  0.00           H  
HETATM   48  H9  UNL     1      -2.071  -0.667  -2.383  1.00  0.00           H  
HETATM   49  H10 UNL     1      -5.020  -2.409   0.417  1.00  0.00           H  
HETATM   50  H11 UNL     1      -5.032   0.907  -0.246  1.00  0.00           H  
HETATM   51  H12 UNL     1      -3.843   1.683   1.681  1.00  0.00           H  
HETATM   52  H13 UNL     1      -5.174   2.797   1.264  1.00  0.00           H  
HETATM   53  H14 UNL     1      -6.340   2.283   2.942  1.00  0.00           H  
HETATM   54  H15 UNL     1      -7.493   1.185   1.490  1.00  0.00           H  
HETATM   55  H16 UNL     1      -6.777   1.688  -1.255  1.00  0.00           H  
HETATM   56  H17 UNL     1      -8.360  -0.385  -0.590  1.00  0.00           H  
HETATM   57  H18 UNL     1      -7.568  -2.130   1.189  1.00  0.00           H  
HETATM   58  H19 UNL     1      -6.206  -0.563  -1.606  1.00  0.00           H  
HETATM   59  H20 UNL     1      -6.433  -3.179  -0.834  1.00  0.00           H  
HETATM   60  H21 UNL     1       2.099  -2.158  -0.623  1.00  0.00           H  
HETATM   61  H22 UNL     1       1.795  -2.478  -2.695  1.00  0.00           H  
HETATM   62  H23 UNL     1       4.302  -2.531  -0.008  1.00  0.00           H  
HETATM   63  H24 UNL     1       4.890  -1.786  -2.699  1.00  0.00           H  
HETATM   64  H25 UNL     1       8.877   3.357   1.979  1.00  0.00           H  
CONECT    1    2   40   41
CONECT    2    3    3   39
CONECT    3    4
CONECT    4    5    5    8
CONECT    5    6   37
CONECT    6    7    7
CONECT    7    8   42
CONECT    8    9
CONECT    9   10   35   43
CONECT   10   11
CONECT   11   12   33   44
CONECT   12   13   45   46
CONECT   13   14
CONECT   14   15   15   16   17
CONECT   16   47
CONECT   17   18
CONECT   18   19   19   20   21
CONECT   20   48
CONECT   21   22
CONECT   22   23   31   49
CONECT   23   24
CONECT   24   25   27   50
CONECT   25   26   51   52
CONECT   26   53
CONECT   27   28   29   54
CONECT   28   55
CONECT   29   30   31   56
CONECT   30   57
CONECT   31   32   58
CONECT   32   59
CONECT   33   34   35   60
CONECT   34   61
CONECT   35   36   62
CONECT   36   63
CONECT   37   38   38   39
CONECT   39   64
END

HMDB0001163
     RDKit          3D
Guanosine diphosphate mannose
 64 67  0  0  0  0  0  0  0  0999 V2000
    7.3990    4.1261    0.0313 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3519    2.8567    0.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4716    1.9250    0.2478 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4051    0.7139    0.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2692    0.4509    1.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9868   -0.8224    2.2559 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9929   -1.2921    1.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6227   -0.3621    0.5919 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6077   -0.3998   -0.4424 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4020    0.1533   -0.0327 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5636   -0.1426   -1.1091 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1184    0.1157   -0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7304   -0.6750    0.2887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8684   -0.4524    0.7139 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.8839    0.0903    2.1458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6260    0.7290   -0.2391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7700   -1.8666    0.6941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7671   -1.9635   -0.6699 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.2214   -3.3828   -0.8829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7997   -1.5424   -2.0118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0095   -0.8715   -0.5606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1431   -1.3567    0.0819 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2836   -0.5470    1.2306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5036    0.7438    0.7524 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9452    1.7943    1.6779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5097    1.7412    2.9419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9925    0.8941    0.5474 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3020    1.8380   -0.4279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4951   -0.4741    0.0692 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8680   -1.1898    1.1940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3963   -1.1881   -0.7216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9532   -2.4029   -1.1280 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8001   -1.6229   -1.2985 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6432   -1.9691   -2.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2486   -1.7990   -0.8247 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0472   -2.2940   -1.8759 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1652    1.4048    2.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9543    1.1789    3.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2085    2.6049    1.6877 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5550    4.7676    0.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2291    4.4899   -0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5730   -2.2740    1.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9926    0.1037   -1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8890    0.4483   -1.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5236   -0.1018   -1.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9787    1.1982   -0.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0384    1.0093   -0.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0709   -0.6666   -2.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0198   -2.4092    0.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0321    0.9067   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8426    1.6834    1.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1744    2.7975    1.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3402    2.2828    2.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4929    1.1851    1.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7767    1.6881   -1.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3600   -0.3851   -0.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5678   -2.1301    1.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2056   -0.5627   -1.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4334   -3.1787   -0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0988   -2.1579   -0.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7950   -2.4782   -2.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3023   -2.5310   -0.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8903   -1.7865   -2.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8775    3.3573    1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  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
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 11 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
  5 37  1  0
 37 38  2  0
 37 39  1  0
 39  2  1  0
  8  4  1  0
 35  9  1  0
 31 22  1  0
  1 40  1  0
  1 41  1  0
  7 42  1  0
  9 43  1  6
 11 44  1  6
 12 45  1  0
 12 46  1  0
 16 47  1  0
 20 48  1  0
 22 49  1  1
 24 50  1  6
 25 51  1  0
 25 52  1  0
 26 53  1  0
 27 54  1  1
 28 55  1  0
 29 56  1  6
 30 57  1  0
 31 58  1  6
 32 59  1  0
 33 60  1  1
 34 61  1  0
 35 62  1  1
 36 63  1  0
 39 64  1  0
M  END

Synonyms

Value	Source
GDP-D-Mannose	ChEBI
GDPmannose	ChEBI
Guanosine 5'-(trihydrogen diphosphate), mono-alpha-D-mannopyranosyl ester	ChEBI
Guanosine diphosphomannose	ChEBI
Guanosine pyrophosphate mannose	ChEBI
GDP-alpha-D-Mannose	Kegg
Guanosine 5'-(trihydrogen diphosphate), mono-a-D-mannopyranosyl ester	Generator
Guanosine 5'-(trihydrogen diphosphate), mono-α-D-mannopyranosyl ester	Generator
Guanosine 5'-(trihydrogen diphosphoric acid), mono-a-D-mannopyranosyl ester	Generator
Guanosine 5'-(trihydrogen diphosphoric acid), mono-alpha-D-mannopyranosyl ester	Generator
Guanosine 5'-(trihydrogen diphosphoric acid), mono-α-D-mannopyranosyl ester	Generator
Guanosine pyrophosphoric acid mannose	Generator
GDP-a-D-Mannose	Generator
GDP-Α-D-mannose	Generator
Guanosine diphosphoric acid mannose	Generator
GDP Mannose	HMDB
GDP-Glucose	HMDB
GDP-Mannose	HMDB
Pyrophosphate mannose, guanosine	HMDB
Diphosphomannose, guanosine	HMDB
Mannose, guanosine diphosphate	HMDB
Diphosphate mannose, guanosine	HMDB
Mannose, guanosine pyrophosphate	HMDB
Mannose, GDP	HMDB
Guanosine 5'-(trihydrogen diphosphate) p'-mannosyl ester	HMDB
Guanosine 5'-(trihydrogen pyrophosphate) mono-D-mannosyl ester	HMDB
Guanosine 5'-(trihydrogen pyrophosphate) monomannopyranosyl ester	HMDB
Guanosine 5'-(trihydrogen pyrophosphate) monomannosyl ester	HMDB
Guanosine 5'-diphosphate D-mannose	HMDB
Guanosine 5'-pyrophosphate D-mannosyl ester	HMDB
Guanosine 5'-pyrophosphate alpha-D-mannosyl ester	HMDB
Guanosine 5'-pyrophosphate α-D-mannosyl ester	HMDB
Guanosine 5’-(trihydrogen diphosphate) p’-mannosyl ester	HMDB
Guanosine 5’-(trihydrogen pyrophosphate) mono-D-mannosyl ester	HMDB
Guanosine 5’-(trihydrogen pyrophosphate) monomannopyranosyl ester	HMDB
Guanosine 5’-(trihydrogen pyrophosphate) monomannosyl ester	HMDB
Guanosine 5’-diphosphate D-mannose	HMDB
Guanosine 5’-pyrophosphate D-mannosyl ester	HMDB
Guanosine 5’-pyrophosphate α-D-mannosyl ester	HMDB
Guanosine diphosphate mannose	HMDB

Molecular Formula

C₁₆H₂₅N₅O₁₆P₂

Average Mass

605.3411

Monoisotopic Mass

605.077152801

IUPAC Name

[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

Traditional Name

guanosine diphosphomannose

CAS Registry Number

3123-67-9

SMILES

NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C(=O)N1

InChI Identifier

InChI=1S/C16H25N5O16P2/c17-16-19-12-6(13(28)20-16)18-3-21(12)14-10(26)8(24)5(34-14)2-33-38(29,30)37-39(31,32)36-15-11(27)9(25)7(23)4(1-22)35-15/h3-5,7-11,14-15,22-27H,1-2H2,(H,29,30)(H,31,32)(H3,17,19,20,28)/t4-,5-,7-,8-,9+,10-,11+,14-,15-/m1/s1

InChI Key

MVMSCBBUIHUTGJ-GDJBGNAASA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine nucleotide sugars

Direct Parent

Purine nucleotide sugars

Alternative Parents

Substituents

Purine nucleotide sugar
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Hydroxypyrimidine
Monoalkyl phosphate
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Pyrimidine
Heteroaromatic compound
Tetrahydrofuran
Imidazole
Azole
Secondary alcohol
Polyol
Oxacycle
Organoheterocyclic compound
Azacycle
Organic oxygen compound
Alcohol
Organic oxide
Primary alcohol
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

GDP-D-mannose (CHEBI:15820 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	7.77 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-5.3	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	327.43 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	118.51 m³·mol⁻¹	ChemAxon
Polarizability	48.72 Å³	ChemAxon
Number of Rings	4	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

Biospecimen Locations

Feces

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
MMDBp0192050	Alpha-1,3/1,6-mannosyltransferase ALG2	Enzyme	Q9H553	Homo sapiens
MMDBp0192051	Dolichol-phosphate mannosyltransferase	Enzyme	O60762	Homo sapiens
MMDBp0192052	GDP-mannose 4,6 dehydratase	Enzyme	O60547	Homo sapiens
MMDBp0193507	Chitobiosyldiphosphodolichol beta-mannosyltransferase	Enzyme	Q9BT22	Homo sapiens
MMDBp0193929	Mannose-1-phosphate guanyltransferase beta	Unknown	Q9Y5P6	Homo sapiens
MMDBp0193930	Mannose-1-phosphate guanyltransferase alpha	Unknown	Q96IJ6	Homo sapiens
MMDBp0196683	GDP-Man:Man(3)GlcNAc(2)-PP-Dol alpha-1,2-mannosyltransferase	Unknown	Q2TAA5
MMDBp0196786	Dolichol phosphate-mannose biosynthesis regulatory protein	Unknown	O94777
MMDBp0196787	Dolichol-phosphate mannosyltransferase subunit 3	Unknown	Q9P2X0

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018330	D-Mannose 1-phosphate	Guanosine diphosphate mannose	Mannose-1-phosphate guanylyltransferase	Transfer of a GMP	PathBank	31602464
MMDBr0018331	Guanosine diphosphate mannose	GDP-4-Dehydro-6-deoxy-D-mannose	GDP-mannose 4,6-dehydratase	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0018479	Guanosine triphosphate	Guanosine diphosphate mannose	Mannose-1-phosphate guanylyltransferase	Transfer of a GMP	PathBank	31602464
MMDBr0018480	Guanosine diphosphate mannose	GDP-4-dehydro-6-deoxy-Œ±-D-mannose	GDP-mannose 4,6-dehydratase	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0018855	Guanosine diphosphate mannose	GDP-4-Dehydro-6-L-deoxygalactose	GDP-mannose 4,6-dehydratase	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0019560	D-Mannose 1-phosphate	Guanosine diphosphate mannose	Mannose-1-phosphate guanyltransferase		PathBank	31602464
MMDBr0020032	Guanosine diphosphate mannose	Guanosine diphosphate	Chitobiosyldiphosphodolichol beta-mannosyltransferase	Transfer of a mannosyl group	PathBank	31602464
MMDBr0020033	Guanosine diphosphate mannose	Guanosine diphosphate	Alpha-1,3/1,6-mannosyltransferase ALG2	Transfer of a mannosyl group	PathBank	31602464
MMDBr0020034	Guanosine diphosphate mannose	Guanosine diphosphate	Alpha-1,3/1,6-mannosyltransferase ALG2	Transfer of a mannosyl group	PathBank	31602464
MMDBr0020035	Guanosine diphosphate mannose	Guanosine diphosphate	GDP-Man:Man(3)GlcNAc(2)-PP-Dol alpha-1,2-mannosyltransferase	Transfer of a mannosyl group	PathBank	31602464
MMDBr0020036	Guanosine diphosphate mannose	Guanosine diphosphate	Dolichol-phosphate mannosyltransferase	Transfer of a mannosyl group	PathBank	31602464
MMDBr0024464	N,N'-diacetylchitobiosyldiphosphodolichol	Guanosine diphosphate	Chitobiosyldiphosphodolichol beta-mannosyltransferase	Transfer of a mannosyl group	RHEA	34755880
MMDBr0024675	Guanosine diphosphate mannose	Guanosine diphosphate	Bifunctional apolipoprotein N-acyltransferase/polyprenol monophosphomannose synthase	Synthesis	RHEA	34755880
MMDBr0024676	Guanosine diphosphate mannose	Guanosine diphosphate	Dolichol-phosphate mannosyltransferase	Transfer of a mannosyl group	RHEA	34755880
MMDBr0024846	Guanosine diphosphate mannose	Guanosine diphosphate	Alpha-1,3/1,6-mannosyltransferase ALG2	Transfer of a mannosyl group	RHEA	34755880
MMDBr0024847	Guanosine diphosphate mannose	Guanosine diphosphate	Alpha-1,3/1,6-mannosyltransferase ALG2	Transfer of a mannosyl group	RHEA	34755880
MMDBr0024848	Guanosine diphosphate mannose	Guanosine diphosphate	GDP-Man:Man(3)GlcNAc(2)-PP-Dol alpha-1,2-mannosyltransferase	Transfer of a mannosyl group	RHEA	34755880
MMDBr0025265	Guanosine diphosphate mannose	Guanosine diphosphate	Phosphatidyl-myo-inositol mannosyltransferase	Transfer of a mannosyl group	RHEA	34755880
MMDBr0025420	Guanosine diphosphate mannose	Guanosine diphosphate	GDP-mannose-dependent alpha-(1-6)-phosphatidylinositol monomannoside mannosyltransferase	Transfer of a mannosyl group	RHEA	34755880
MMDBr0025421	Guanosine diphosphate mannose	Guanosine diphosphate	GDP-mannose-dependent alpha-(1-6)-phosphatidylinositol monomannoside mannosyltransferase	Transfer of a mannosyl group	RHEA	34755880
MMDBr0025870	Guanosine diphosphate mannose	Guanosine diphosphate	Mannosyl phosphorylinositol ceramide synthase SUR1	Synthesis	RHEA	34755880
MMDBr0025871	Guanosine diphosphate mannose	Guanosine diphosphate	Mannosyl phosphorylinositol ceramide synthase SUR1	Synthesis	RHEA	34755880
MMDBr0025926	Guanosine diphosphate mannose	Guanosine diphosphate	D-rhamnosyltransferase WbpZ	Transfer of a rhamnosyl group	RHEA	34755880

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	Proteobacteria	14	Human feces; Human sputum; Human ; Human pleural fluid plaque; Human stool; Human feces; pleural fluid plaque; bal; Human subgingival plaque; Human saliva	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	138	Human feces; Human sputum; Human ; Human pleural fluid plaque; Human stool; Human feces; pleural fluid plaque; bal; Human subgingival plaque; Human saliva	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	10	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	62	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	127	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	82	Human feces; Human ; Human stool	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	4	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	7	Human feces; Human ; Human stool	Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	4		Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Archaea/Archaea	Crenarchaeota	2		Metabolic reconstruction
Archaea/Archaea	Euryarchaeota	3		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	17	Human feces; Human saliva	Unknown
Eukaryota/Fungi	Basidiomycota	2
Bacteria/Eubacteria	Thermotogae	2
Bacteria/Eubacteria	Aquificae	1

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

External Links

HMDB ID

HMDB0001163

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Guanosine diphosphate mannose

METLIN ID

6045

PubChem Compound

18396

PDB ID

Not Available

ChEBI ID

15820

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Becker DJ, Lowe JB: Fucose: biosynthesis and biological function in mammals. Glycobiology. 2003 Jul;13(7):41R-53R. doi: 10.1093/glycob/cwg054. Epub 2003 Mar 19. [PubMed:12651883 ]

Showing metabocard for Guanosine diphosphate mannose (MMDBc0029575)

MOL for #<Metabolite:0x00005645ca28e5e0>

3D MOL for #<Metabolite:0x00005645ca28e5e0>

3D SDF for #<Metabolite:0x00005645ca28e5e0>

3D-SDF for #<Metabolite:0x00005645ca28e5e0>

PDB for #<Metabolite:0x00005645ca28e5e0>

3D PDB for #<Metabolite:0x00005645ca28e5e0>

SMILES for #<Metabolite:0x00005645ca28e5e0>

INCHI for #<Metabolite:0x00005645ca28e5e0>

Structure for #<Metabolite:0x00005645ca28e5e0>

3D Structure for #<Metabolite:0x00005645ca28e5e0>