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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 09:14:49 UTC

Update Date

2021-09-24 09:14:49 UTC

HMDB ID

HMDB0304367

Secondary Accession Numbers

None

Metabolite Identification

Common Name

GDP-alpha-D-glucose

Description

9-[3,4-dihydroxy-5-({[hydroxy({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl phosphonato]oxy}methyl)oxolan-2-yl]-2-imino-3,9-dihydro-2H-purin-6-olate 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. Based on a literature review very few articles have been published on 9-[3,4-dihydroxy-5-({[hydroxy({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl phosphonato]oxy}methyl)oxolan-2-yl]-2-imino-3,9-dihydro-2H-purin-6-olate.

Structure

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


  Mrv1533005141513002D          

 39 42  0  0  0  0            999 V2000
   -5.7689    6.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4363    6.5339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0152    6.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9290    7.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5964    7.6900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1753    7.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0891    8.3611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5079    7.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7542    7.3912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5941    6.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478    5.8996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9267    5.7503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0129    4.9298    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8334    5.0160    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.1924    4.8436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0991    4.1093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4317    3.6244    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9166    2.9569    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.9468    4.2918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643    3.1395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505    2.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831    1.8341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    2.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.8736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0865    1.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9115    1.4216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831    1.0091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 29 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 32 38  1  0  0  0  0
M  CHG  2  14  -1  18  -1
M  END

HMDB0304367
     RDKit          3D
GDP-alpha-D-glucose
 62 65  0  0  0  0  0  0  0  0999 V2000
    5.6246    3.3133   -0.6634 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9537    2.1008    0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3305    0.9422   -0.2488 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6465   -0.1729    0.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6205   -0.1284    1.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7387   -1.3651    1.8368 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8723   -2.1471    1.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1711   -1.4141    0.2950 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1635   -1.9859   -0.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9583   -2.2193    0.0742 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9427   -1.9822   -0.8136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3137   -0.6314   -0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8141   -0.6858    0.8629 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1381    0.8168    1.2120 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.1178    1.6810    1.9967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2779    1.6642   -0.1940 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.3033    0.6182    2.1114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2063   -0.6509    1.5075 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.3916   -1.5369    0.5943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7369   -1.6031    2.7966 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.5744   -0.1337    0.6633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6167    0.1889    1.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7424   -0.5408    1.1541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7651   -0.6148   -0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9966   -1.4020   -0.6233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9026   -2.6717   -0.0567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6674    0.6989   -0.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8075    0.8425   -1.7330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6312    1.8836   -0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9218    2.4329    0.1644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9523    1.6481    1.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8172    2.4154    1.4920 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5491   -1.8021   -2.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8006   -0.9386   -2.9771 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8884   -1.2080   -1.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8546   -1.4323   -2.7728 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2868    1.0555    1.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1827    1.0741    2.5437 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9163    2.1471    0.9666 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042    3.3565   -1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3994    4.1752   -0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7549   -3.1990    1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5508   -2.9907   -0.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1662   -2.7772   -0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4928   -0.3600   -1.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661    0.1715   -0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3174    0.0345    2.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8869   -1.2386   -0.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9262   -0.8798   -0.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9843   -1.5625   -1.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4263   -2.5506    0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8014    0.7384   -1.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9551    1.8126   -1.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0541    2.6936   -0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4377    1.8484    0.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6692    1.9265    2.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6746    2.6159    2.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6743   -2.7987   -2.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0338   -1.4641   -3.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7155   -0.1311   -1.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6996   -0.7258   -3.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4020    3.0487    1.1802 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  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 22 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
 26 51  1  0
 27 52  1  0
 28 53  1  0
 29 54  1  0
 30 55  1  0
 31 56  1  0
 32 57  1  0
 33 58  1  0
 34 59  1  0
 35 60  1  0
 36 61  1  0
 39 62  1  0
M  CHG  2  16  -1  20  -1
M  END


  Mrv1533005141513002D          

 39 42  0  0  0  0            999 V2000
   -5.7689    6.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4363    6.5339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0152    6.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9290    7.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5964    7.6900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1753    7.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0891    8.3611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5079    7.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7542    7.3912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5941    6.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478    5.8996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9267    5.7503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0129    4.9298    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8334    5.0160    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.1924    4.8436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0991    4.1093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4317    3.6244    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9166    2.9569    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.9468    4.2918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643    3.1395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505    2.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831    1.8341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    2.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.8736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0865    1.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9115    1.4216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831    1.0091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 29 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 32 38  1  0  0  0  0
M  CHG  2  14  -1  18  -1
M  END
> <DATABASE_ID>
HMDB0304367

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC2=C(N=CN2C2OC(COP([O-])(=O)OP([O-])(=O)OC3OC(CO)C(O)C(O)C3O)C(O)C2O)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)/p-2

> <INCHI_KEY>
MVMSCBBUIHUTGJ-UHFFFAOYSA-L

> <FORMULA>
C16H23N5O16P2

> <MOLECULAR_WEIGHT>
603.328

> <EXACT_MASS>
603.062600836

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
50.77044957395208

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl phosphonato]oxy}phosphonate

> <ALOGPS_LOGP>
-1.73

> <JCHEM_LOGP>
-5.287584132999999

> <ALOGPS_LOGS>
-1.78

> <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>
333.0899999999999

> <JCHEM_REFRACTIVITY>
116.2679

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.06e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl phosphonato]oxyphosphonate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304367
     RDKit          3D
GDP-alpha-D-glucose
 62 65  0  0  0  0  0  0  0  0999 V2000
    5.6246    3.3133   -0.6634 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9537    2.1008    0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3305    0.9422   -0.2488 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6465   -0.1729    0.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6205   -0.1284    1.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7387   -1.3651    1.8368 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8723   -2.1471    1.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1711   -1.4141    0.2950 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1635   -1.9859   -0.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9583   -2.2193    0.0742 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9427   -1.9822   -0.8136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3137   -0.6314   -0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8141   -0.6858    0.8629 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1381    0.8168    1.2120 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.1178    1.6810    1.9967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2779    1.6642   -0.1940 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.3033    0.6182    2.1114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2063   -0.6509    1.5075 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.3916   -1.5369    0.5943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7369   -1.6031    2.7966 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.5744   -0.1337    0.6633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6167    0.1889    1.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7424   -0.5408    1.1541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7651   -0.6148   -0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9966   -1.4020   -0.6233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9026   -2.6717   -0.0567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6674    0.6989   -0.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8075    0.8425   -1.7330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6312    1.8836   -0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9218    2.4329    0.1644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9523    1.6481    1.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8172    2.4154    1.4920 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5491   -1.8021   -2.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8006   -0.9386   -2.9771 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8884   -1.2080   -1.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8546   -1.4323   -2.7728 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2868    1.0555    1.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1827    1.0741    2.5437 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9163    2.1471    0.9666 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042    3.3565   -1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3994    4.1752   -0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7549   -3.1990    1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5508   -2.9907   -0.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1662   -2.7772   -0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4928   -0.3600   -1.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661    0.1715   -0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3174    0.0345    2.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8869   -1.2386   -0.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9262   -0.8798   -0.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9843   -1.5625   -1.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4263   -2.5506    0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8014    0.7384   -1.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9551    1.8126   -1.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0541    2.6936   -0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4377    1.8484    0.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6692    1.9265    2.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6746    2.6159    2.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6743   -2.7987   -2.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0338   -1.4641   -3.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7155   -0.1311   -1.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6996   -0.7258   -3.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4020    3.0487    1.1802 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  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 22 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
 26 51  1  0
 27 52  1  0
 28 53  1  0
 29 54  1  0
 30 55  1  0
 31 56  1  0
 32 57  1  0
 33 58  1  0
 34 59  1  0
 35 60  1  0
 36 61  1  0
 39 62  1  0
M  CHG  2  16  -1  20  -1
M  END

HEADER    PROTEIN                                 14-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-15         0                                  
HETATM    1  C   UNK     0     -10.769  11.291   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -12.015  12.197   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -9.362  11.918   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.201  13.449   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0     -10.447  14.355   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -7.794  14.076   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.633  15.607   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -6.548  13.171   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.141  13.797   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -6.709  11.639   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -8.116  11.013   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -5.463  10.734   0.000  0.00  0.00           O+0
HETATM   13  P   UNK     0      -5.624   9.202   0.000  0.00  0.00           P+0
HETATM   14  O   UNK     0      -7.156   9.363   0.000  0.00  0.00           O-1
HETATM   15  O   UNK     0      -4.093   9.041   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -5.785   7.671   0.000  0.00  0.00           O+0
HETATM   17  P   UNK     0      -4.539   6.766   0.000  0.00  0.00           P+0
HETATM   18  O   UNK     0      -5.444   5.520   0.000  0.00  0.00           O-1
HETATM   19  O   UNK     0      -3.634   8.011   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.293   5.860   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.454   4.329   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.208   3.424   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.744   3.899   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.268   5.364   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.161   2.654   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.701   2.654   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.208   1.884   0.000  0.00  0.00           O+0
HETATM   29  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       2.530   0.237   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       5.198   0.237   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0       3.864  -2.073   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.530  -4.383   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1                                                            
CONECT    3    1    4   11                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10    3                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27   22                                                       
CONECT   29   27   30   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   38                                                  
CONECT   33   32   29   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39   32                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

COMPND    HMDB0304367
HETATM    1  N1  UNL     1       5.625   3.313  -0.663  1.00  0.00           N  
HETATM    2  C1  UNL     1       5.954   2.101   0.025  1.00  0.00           C  
HETATM    3  N2  UNL     1       5.331   0.942  -0.249  1.00  0.00           N  
HETATM    4  C2  UNL     1       5.646  -0.173   0.397  1.00  0.00           C  
HETATM    5  C3  UNL     1       6.621  -0.128   1.351  1.00  0.00           C  
HETATM    6  N3  UNL     1       6.739  -1.365   1.837  1.00  0.00           N  
HETATM    7  C4  UNL     1       5.872  -2.147   1.210  1.00  0.00           C  
HETATM    8  N4  UNL     1       5.171  -1.414   0.295  1.00  0.00           N  
HETATM    9  C5  UNL     1       4.164  -1.986  -0.535  1.00  0.00           C  
HETATM   10  O1  UNL     1       2.958  -2.219   0.074  1.00  0.00           O  
HETATM   11  C6  UNL     1       1.943  -1.982  -0.814  1.00  0.00           C  
HETATM   12  C7  UNL     1       1.314  -0.631  -0.446  1.00  0.00           C  
HETATM   13  O2  UNL     1       0.814  -0.686   0.863  1.00  0.00           O  
HETATM   14  P1  UNL     1       0.138   0.817   1.212  1.00  0.00           P  
HETATM   15  O3  UNL     1       1.118   1.681   1.997  1.00  0.00           O  
HETATM   16  O4  UNL     1      -0.278   1.664  -0.194  1.00  0.00           O1-
HETATM   17  O5  UNL     1      -1.303   0.618   2.111  1.00  0.00           O  
HETATM   18  P2  UNL     1      -2.206  -0.651   1.507  1.00  0.00           P  
HETATM   19  O6  UNL     1      -1.392  -1.537   0.594  1.00  0.00           O  
HETATM   20  O7  UNL     1      -2.737  -1.603   2.797  1.00  0.00           O1-
HETATM   21  O8  UNL     1      -3.574  -0.134   0.663  1.00  0.00           O  
HETATM   22  C8  UNL     1      -4.617   0.189   1.522  1.00  0.00           C  
HETATM   23  O9  UNL     1      -5.742  -0.541   1.154  1.00  0.00           O  
HETATM   24  C9  UNL     1      -5.765  -0.615  -0.227  1.00  0.00           C  
HETATM   25  C10 UNL     1      -6.997  -1.402  -0.623  1.00  0.00           C  
HETATM   26  O10 UNL     1      -6.903  -2.672  -0.057  1.00  0.00           O  
HETATM   27  C11 UNL     1      -5.667   0.699  -0.912  1.00  0.00           C  
HETATM   28  O11 UNL     1      -6.807   0.842  -1.733  1.00  0.00           O  
HETATM   29  C12 UNL     1      -5.631   1.884  -0.002  1.00  0.00           C  
HETATM   30  O12 UNL     1      -6.922   2.433   0.164  1.00  0.00           O  
HETATM   31  C13 UNL     1      -4.952   1.648   1.302  1.00  0.00           C  
HETATM   32  O13 UNL     1      -3.817   2.415   1.492  1.00  0.00           O  
HETATM   33  C14 UNL     1       2.549  -1.802  -2.188  1.00  0.00           C  
HETATM   34  O14 UNL     1       1.801  -0.939  -2.977  1.00  0.00           O  
HETATM   35  C15 UNL     1       3.888  -1.208  -1.800  1.00  0.00           C  
HETATM   36  O15 UNL     1       4.855  -1.432  -2.773  1.00  0.00           O  
HETATM   37  C16 UNL     1       7.287   1.055   1.660  1.00  0.00           C  
HETATM   38  O16 UNL     1       8.183   1.074   2.544  1.00  0.00           O  
HETATM   39  N5  UNL     1       6.916   2.147   0.967  1.00  0.00           N  
HETATM   40  H1  UNL     1       5.604   3.356  -1.706  1.00  0.00           H  
HETATM   41  H2  UNL     1       5.399   4.175  -0.134  1.00  0.00           H  
HETATM   42  H3  UNL     1       5.755  -3.199   1.406  1.00  0.00           H  
HETATM   43  H4  UNL     1       4.551  -2.991  -0.877  1.00  0.00           H  
HETATM   44  H5  UNL     1       1.166  -2.777  -0.818  1.00  0.00           H  
HETATM   45  H6  UNL     1       0.493  -0.360  -1.117  1.00  0.00           H  
HETATM   46  H7  UNL     1       2.066   0.171  -0.472  1.00  0.00           H  
HETATM   47  H8  UNL     1      -4.317   0.034   2.571  1.00  0.00           H  
HETATM   48  H9  UNL     1      -4.887  -1.239  -0.532  1.00  0.00           H  
HETATM   49  H10 UNL     1      -7.926  -0.880  -0.318  1.00  0.00           H  
HETATM   50  H11 UNL     1      -6.984  -1.563  -1.732  1.00  0.00           H  
HETATM   51  H12 UNL     1      -6.426  -2.551   0.808  1.00  0.00           H  
HETATM   52  H13 UNL     1      -4.801   0.738  -1.632  1.00  0.00           H  
HETATM   53  H14 UNL     1      -6.955   1.813  -1.899  1.00  0.00           H  
HETATM   54  H15 UNL     1      -5.054   2.694  -0.537  1.00  0.00           H  
HETATM   55  H16 UNL     1      -7.438   1.848   0.764  1.00  0.00           H  
HETATM   56  H17 UNL     1      -5.669   1.927   2.121  1.00  0.00           H  
HETATM   57  H18 UNL     1      -3.675   2.616   2.460  1.00  0.00           H  
HETATM   58  H19 UNL     1       2.674  -2.799  -2.652  1.00  0.00           H  
HETATM   59  H20 UNL     1       1.034  -1.464  -3.326  1.00  0.00           H  
HETATM   60  H21 UNL     1       3.716  -0.131  -1.623  1.00  0.00           H  
HETATM   61  H22 UNL     1       4.700  -0.726  -3.478  1.00  0.00           H  
HETATM   62  H23 UNL     1       7.402   3.049   1.180  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   17   18
CONECT   18   19   19   20   21
CONECT   21   22
CONECT   22   23   31   47
CONECT   23   24
CONECT   24   25   27   48
CONECT   25   26   49   50
CONECT   26   51
CONECT   27   28   29   52
CONECT   28   53
CONECT   29   30   31   54
CONECT   30   55
CONECT   31   32   56
CONECT   32   57
CONECT   33   34   35   58
CONECT   34   59
CONECT   35   36   60
CONECT   36   61
CONECT   37   38   38   39
CONECT   39   62
END

HMDB0304367
     RDKit          3D
GDP-alpha-D-glucose
 62 65  0  0  0  0  0  0  0  0999 V2000
    5.6246    3.3133   -0.6634 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9537    2.1008    0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3305    0.9422   -0.2488 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6465   -0.1729    0.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6205   -0.1284    1.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7387   -1.3651    1.8368 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8723   -2.1471    1.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1711   -1.4141    0.2950 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1635   -1.9859   -0.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9583   -2.2193    0.0742 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9427   -1.9822   -0.8136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3137   -0.6314   -0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8141   -0.6858    0.8629 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1381    0.8168    1.2120 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.1178    1.6810    1.9967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2779    1.6642   -0.1940 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.3033    0.6182    2.1114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2063   -0.6509    1.5075 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.3916   -1.5369    0.5943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7369   -1.6031    2.7966 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.5744   -0.1337    0.6633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6167    0.1889    1.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7424   -0.5408    1.1541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7651   -0.6148   -0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9966   -1.4020   -0.6233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9026   -2.6717   -0.0567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6674    0.6989   -0.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8075    0.8425   -1.7330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6312    1.8836   -0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9218    2.4329    0.1644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9523    1.6481    1.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8172    2.4154    1.4920 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5491   -1.8021   -2.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8006   -0.9386   -2.9771 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8884   -1.2080   -1.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8546   -1.4323   -2.7728 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2868    1.0555    1.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1827    1.0741    2.5437 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9163    2.1471    0.9666 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042    3.3565   -1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3994    4.1752   -0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7549   -3.1990    1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5508   -2.9907   -0.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1662   -2.7772   -0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4928   -0.3600   -1.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661    0.1715   -0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3174    0.0345    2.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8869   -1.2386   -0.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9262   -0.8798   -0.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9843   -1.5625   -1.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4263   -2.5506    0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8014    0.7384   -1.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9551    1.8126   -1.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0541    2.6936   -0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4377    1.8484    0.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6692    1.9265    2.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6746    2.6159    2.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6743   -2.7987   -2.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0338   -1.4641   -3.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7155   -0.1311   -1.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6996   -0.7258   -3.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4020    3.0487    1.1802 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  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 22 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
 26 51  1  0
 27 52  1  0
 28 53  1  0
 29 54  1  0
 30 55  1  0
 31 56  1  0
 32 57  1  0
 33 58  1  0
 34 59  1  0
 35 60  1  0
 36 61  1  0
 39 62  1  0
M  CHG  2  16  -1  20  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9-[3,4-Dihydroxy-5-({[hydroxy({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl phosphonato]oxy}methyl)oxolan-2-yl]-2-imino-3,9-dihydro-2H-purin-6-olic acid	Generator

Chemical Formula

C₁₆H₂₃N₅O₁₆P₂

Average Molecular Weight

603.328

Monoisotopic Molecular Weight

603.062600836

IUPAC Name

[5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl phosphonato]oxy}phosphonate

Traditional Name

[5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl phosphonato]oxyphosphonate

CAS Registry Number

Not Available

SMILES

NC1=NC2=C(N=CN2C2OC(COP([O-])(=O)OP([O-])(=O)OC3OC(CO)C(O)C(O)C3O)C(O)C2O)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)/p-2

InChI Key

MVMSCBBUIHUTGJ-UHFFFAOYSA-L

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
6-oxopurine
Hypoxanthine
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Aminopyrimidine
Pyrimidone
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Pyrimidine
Vinylogous amide
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Polyol
Organoheterocyclic compound
Azacycle
Oxacycle
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Amine
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Primary alcohol
Primary amine
Organooxygen compound
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a GDP-sugar (GDP-MANNOSE )

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1.7	ALOGPS
logP	-5.3	ChemAxon
logS	-1.8	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	8	ChemAxon
Polar Surface Area	333.09 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	116.27 m³·mol⁻¹	ChemAxon
Polarizability	50.77 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	220.855	32859911
AllCCS	[M+H-H2O]+	219.553	32859911
AllCCS	[M+Na]+	222.353	32859911
AllCCS	[M+NH4]+	222.024	32859911
AllCCS	[M-H]-	208.331	32859911
AllCCS	[M+Na-2H]-	208.722	32859911
AllCCS	[M+HCOO]-	209.307	32859911
DeepCCS	[M+H]+	214.127	30932474
DeepCCS	[M-H]-	211.731	30932474
DeepCCS	[M-2H]-	244.616	30932474
DeepCCS	[M+Na]+	220.04	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.9616 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	10.13 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	924.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	211.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	53.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	64.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	348.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	334.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	833.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	613.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	129.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1097.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	222.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	267.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	715.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	405.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	522.5 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030880

KNApSAcK ID

Not Available

Chemspider ID

19501249

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20705993

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for GDP-alpha-D-glucose (HMDB0304367)

MOL for HMDB0304367 (GDP-alpha-D-glucose)

3D MOL for HMDB0304367 (GDP-alpha-D-glucose)

3D SDF for HMDB0304367 (GDP-alpha-D-glucose)

3D-SDF for HMDB0304367 (GDP-alpha-D-glucose)

PDB for HMDB0304367 (GDP-alpha-D-glucose)

3D PDB for HMDB0304367 (GDP-alpha-D-glucose)

SMILES for HMDB0304367 (GDP-alpha-D-glucose)

INCHI for HMDB0304367 (GDP-alpha-D-glucose)

Structure for HMDB0304367 (GDP-alpha-D-glucose)

3D Structure for HMDB0304367 (GDP-alpha-D-glucose)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices