MiMeDB: Showing metabocard for GDP-L-Fucose (MMDBc0029554)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:32:05 UTC

Update Date

2024-04-30 19:37:50 UTC

Metabolite ID

MMDBc0029554

Metabolite Identification

Common Name

GDP-L-Fucose

Description

GDP-L-fucose is a sugar nucleotide and a readily available source of fucose. The monosaccharide plays several important metabolic roles in complex carbohydrates and in glycoproteins. Fucosylated oligosaccharides are involved in cell-cell recognition, selectin-mediated leukocyte-endothelial adhesion, and mouse embryogenesis. Fucose is made available during the synthesis of fucosylated glycolipids, oligosaccharides, and glycoproteins via a sugar nucleotide intermediate, specifically GDP-L-fucose. GTP-L-fucose pyrophosphorylase (GFPP, E. C. 2.7.7.30) catalyzes the reversible condensation of guanosine triphosphate and beta-L-fucose-1-phosphate to form the nucleotide-sugar GDP-L-fucose.

Structure

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


  Mrv1652309042000182D          

 38 41  0  0  1  0            999 V2000
    3.6062    1.4009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8194    1.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6027   -0.2364    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0897    2.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8194    2.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0995    1.2279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9252    0.2505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3557   -1.0092    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6132    2.7382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0995    2.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3868    1.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -0.2223    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5300   -1.0092    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8426   -1.6690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3868    2.4805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0960    3.7121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6739    1.2421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4820    0.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0607   -1.6760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7692   -0.3776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0529   -0.3776    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8786   -0.3776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0494    0.4410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0635   -1.2879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6937   -0.3776    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6902    0.4410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7043   -1.2245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2287   -1.6090    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9450   -0.3811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9450   -2.0254    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5194   -2.0254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6613   -0.7904    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6613   -1.6090    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -5.3635   -0.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3635   -2.0254    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
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 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
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 34 37  1  6  0  0  0
 35 38  1  6  0  0  0
  5  9  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 34 35  1  0  0  0  0
M  END

HMDB0001095
     RDKit          3D
GDP-L-fucose
 63 66  0  0  0  0  0  0  0  0999 V2000
    7.3952    1.6877   -0.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5063    0.4487   -0.7118 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3870    0.9014   -0.0659 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4822   -0.1527    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656   -0.6055   -0.8668 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9423    0.5659   -1.6377 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.5956    1.7218   -0.7501 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8565    1.0578   -2.9908 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4807   -0.0756   -2.3057 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218   -0.8539   -1.0654 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.4601   -2.0942   -0.5997 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9209    0.2893    0.2924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8952   -1.1290   -1.0934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6031    0.0640   -1.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3968    0.2924   -0.2258 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4234    1.1239   -0.1507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1323    0.7231    1.0165 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4679    1.2040    1.0299 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8672    2.2565    1.7489 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.5784    1.5500    0.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8440    1.3110    0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.9320   -0.5423   -0.9462 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9025   -0.8530    1.7829 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1336   -1.2352    1.0409 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1584   -2.4125    0.2731 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5878   -0.9391    1.3884 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6987    0.0043    2.4037 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2975   -0.5400    0.1237 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5387   -0.0321    0.4596 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7475    2.5569   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1723    1.4594   -1.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8570    1.8662    0.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7638    0.4042    0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2824    1.9098   -2.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6332   -0.0028    0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.9489    0.0839   -1.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6558    0.2530    2.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2783   -0.6388    0.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
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 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 17 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
  4 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37  2  1  0
 31 15  1  0
 28 18  1  0
 28 21  2  0
  1 39  1  0
  1 40  1  0
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  2 42  1  6
  4 43  1  0
  8 44  1  0
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 35 60  1  1
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 37 62  1  6
 38 63  1  0
M  END


  Mrv1652309042000182D          

 38 41  0  0  1  0            999 V2000
    3.6062    1.4009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8194    1.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6027   -0.2364    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0897    2.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8194    2.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0995    1.2279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9252    0.2505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3557   -1.0092    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6132    2.7382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0995    2.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3868    1.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -0.2223    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5300   -1.0092    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8426   -1.6690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3868    2.4805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0960    3.7121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6739    1.2421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3635   -2.0254    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
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  3  7  1  0  0  0  0
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  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
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 13 19  1  6  0  0  0
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 30 32  1  0  0  0  0
 30 33  1  1  0  0  0
 31 34  1  0  0  0  0
 32 35  1  0  0  0  0
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 35 38  1  6  0  0  0
  5  9  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029554

> <DATABASE_NAME>
MIME

> <SMILES>
C[C@@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=C(N)NC3=O)[C@@H](O)[C@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H25N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,7-11,14-15,22-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5+,7+,8+,9+,10+,11-,14+,15?/m0/s1

> <INCHI_KEY>
LQEBEXMHBLQMDB-QIXZNPMTSA-N

> <FORMULA>
C16H25N5O15P2

> <MOLECULAR_WEIGHT>
589.3417

> <EXACT_MASS>
589.082238179

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
48.2224639920485

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <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]({[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid

> <ALOGPS_LOGP>
-1.69

> <JCHEM_LOGP>
-4.240674166333333

> <ALOGPS_LOGS>
-1.92

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.1763296428152783

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7326083975660058

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6122141796192597

> <JCHEM_POLAR_SURFACE_AREA>
307.2

> <JCHEM_REFRACTIVITY>
116.96759999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gdp-L-fucose

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001095
     RDKit          3D
GDP-L-fucose
 63 66  0  0  0  0  0  0  0  0999 V2000
    7.3952    1.6877   -0.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5063    0.4487   -0.7118 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3870    0.9014   -0.0659 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4822   -0.1527    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656   -0.6055   -0.8668 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9423    0.5659   -1.6377 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.5956    1.7218   -0.7501 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8565    1.0578   -2.9908 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4807   -0.0756   -2.3057 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218   -0.8539   -1.0654 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.4601   -2.0942   -0.5997 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9209    0.2893    0.2924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8952   -1.1290   -1.0934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6031    0.0640   -1.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3968    0.2924   -0.2258 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4234    1.1239   -0.1507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1323    0.7231    1.0165 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4679    1.2040    1.0299 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8672    2.2565    1.7489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1856    2.4925    1.5396 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5784    1.5500    0.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8440    1.3110    0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7866    2.0613    0.4774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0127    0.2590   -0.6448 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9320   -0.5423   -0.9462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2965   -1.7060   -1.7023 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7269   -0.3143   -0.4700 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5247    0.7197    0.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0803   -0.8024    0.9063 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3778   -1.4109    2.0944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5738   -0.9473    0.5807 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9025   -0.8530    1.7829 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1336   -1.2352    1.0409 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1584   -2.4125    0.2731 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5878   -0.9391    1.3884 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6987    0.0043    2.4037 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2975   -0.5400    0.1237 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5387   -0.0321    0.4596 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7475    2.5569   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1723    1.4594   -1.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8570    1.8662    0.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3230    0.0456   -1.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638    0.4042    0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2824    1.9098   -2.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6332   -0.0028    0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8926    0.8330   -1.6880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781   -0.1425   -2.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5699    0.9282    0.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5452    1.0234    1.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2351    2.8312    2.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9489    0.0839   -1.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7921   -2.4487   -1.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1084   -1.8247   -2.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6258   -1.1864    0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5382   -2.3531    1.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3449   -1.8764    0.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3776   -0.0334    1.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6270   -1.4960    1.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9865   -2.9284    0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0486   -1.8982    1.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6558    0.2530    2.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4602   -1.4536   -0.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2783   -0.6388    0.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 17 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
  4 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37  2  1  0
 31 15  1  0
 28 18  1  0
 28 21  2  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  2 42  1  6
  4 43  1  0
  8 44  1  0
 12 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  1
 17 49  1  1
 19 50  1  0
 24 51  1  0
 26 52  1  0
 26 53  1  0
 29 54  1  6
 30 55  1  0
 31 56  1  6
 32 57  1  0
 33 58  1  1
 34 59  1  0
 35 60  1  1
 36 61  1  0
 37 62  1  6
 38 63  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       6.732   2.615   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       5.263   3.083   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.725  -0.441   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.634   3.847   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.263   4.630   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       3.919   2.292   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       5.460   0.468   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.264  -1.884   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       6.745   5.111   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.919   5.401   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.589   3.083   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.235  -0.415   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.723  -1.884   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.173  -3.115   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       2.589   4.630   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       3.913   6.929   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       1.258   2.319   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.766   0.046   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.847  -3.129   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.436  -0.705   0.000  0.00  0.00           O+0
HETATM   21  P   UNK     0      -0.099  -0.705   0.000  0.00  0.00           P+0
HETATM   22  O   UNK     0      -1.640  -0.705   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.092   0.823   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.119  -2.404   0.000  0.00  0.00           O+0
HETATM   25  P   UNK     0      -3.162  -0.705   0.000  0.00  0.00           P+0
HETATM   26  O   UNK     0      -4.703  -0.711   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -3.155   0.823   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -3.181  -2.286   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -6.027  -1.475   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.027  -3.003   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -7.364  -0.711   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -7.364  -3.781   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -4.703  -3.781   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -8.701  -1.475   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -8.701  -3.003   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -7.364  -5.309   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0     -10.012  -0.711   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0     -10.012  -3.781   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   33                                                  
CONECT   31   29   34                                                       
CONECT   32   30   35   36                                                  
CONECT   33   30                                                            
CONECT   34   31   37   35                                                  
CONECT   35   32   38   34                                                  
CONECT   36   32                                                            
CONECT   37   34                                                            
CONECT   38   35                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

COMPND    HMDB0001095
HETATM    1  C1  UNL     1       7.395   1.688  -0.901  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.506   0.449  -0.712  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.387   0.901  -0.066  1.00  0.00           O  
HETATM    4  C3  UNL     1       4.482  -0.153   0.287  1.00  0.00           C  
HETATM    5  O2  UNL     1       3.866  -0.606  -0.867  1.00  0.00           O  
HETATM    6  P1  UNL     1       2.942   0.566  -1.638  1.00  0.00           P  
HETATM    7  O3  UNL     1       2.596   1.722  -0.750  1.00  0.00           O  
HETATM    8  O4  UNL     1       3.857   1.058  -2.991  1.00  0.00           O  
HETATM    9  O5  UNL     1       1.481  -0.076  -2.306  1.00  0.00           O  
HETATM   10  P2  UNL     1       0.722  -0.854  -1.065  1.00  0.00           P  
HETATM   11  O6  UNL     1       1.460  -2.094  -0.600  1.00  0.00           O  
HETATM   12  O7  UNL     1       0.921   0.289   0.292  1.00  0.00           O  
HETATM   13  O8  UNL     1      -0.895  -1.129  -1.093  1.00  0.00           O  
HETATM   14  C4  UNL     1      -1.603   0.064  -1.472  1.00  0.00           C  
HETATM   15  C5  UNL     1      -2.397   0.292  -0.226  1.00  0.00           C  
HETATM   16  O9  UNL     1      -3.423   1.124  -0.151  1.00  0.00           O  
HETATM   17  C6  UNL     1      -4.132   0.723   1.017  1.00  0.00           C  
HETATM   18  N1  UNL     1      -5.468   1.204   1.030  1.00  0.00           N  
HETATM   19  C7  UNL     1      -5.867   2.257   1.749  1.00  0.00           C  
HETATM   20  N2  UNL     1      -7.186   2.492   1.540  1.00  0.00           N  
HETATM   21  C8  UNL     1      -7.578   1.550   0.680  1.00  0.00           C  
HETATM   22  C9  UNL     1      -8.844   1.311   0.170  1.00  0.00           C  
HETATM   23  O10 UNL     1      -9.787   2.061   0.477  1.00  0.00           O  
HETATM   24  N3  UNL     1      -9.013   0.259  -0.645  1.00  0.00           N  
HETATM   25  C10 UNL     1      -7.932  -0.542  -0.946  1.00  0.00           C  
HETATM   26  N4  UNL     1      -8.296  -1.706  -1.702  1.00  0.00           N  
HETATM   27  N5  UNL     1      -6.727  -0.314  -0.470  1.00  0.00           N  
HETATM   28  C11 UNL     1      -6.525   0.720   0.342  1.00  0.00           C  
HETATM   29  C12 UNL     1      -4.080  -0.802   0.906  1.00  0.00           C  
HETATM   30  O11 UNL     1      -4.378  -1.411   2.094  1.00  0.00           O  
HETATM   31  C13 UNL     1      -2.574  -0.947   0.581  1.00  0.00           C  
HETATM   32  O12 UNL     1      -1.903  -0.853   1.783  1.00  0.00           O  
HETATM   33  C14 UNL     1       5.134  -1.235   1.041  1.00  0.00           C  
HETATM   34  O13 UNL     1       5.158  -2.412   0.273  1.00  0.00           O  
HETATM   35  C15 UNL     1       6.588  -0.939   1.388  1.00  0.00           C  
HETATM   36  O14 UNL     1       6.699   0.004   2.404  1.00  0.00           O  
HETATM   37  C16 UNL     1       7.297  -0.540   0.124  1.00  0.00           C  
HETATM   38  O15 UNL     1       8.539  -0.032   0.460  1.00  0.00           O  
HETATM   39  H1  UNL     1       6.747   2.557  -1.152  1.00  0.00           H  
HETATM   40  H2  UNL     1       8.172   1.459  -1.624  1.00  0.00           H  
HETATM   41  H3  UNL     1       7.857   1.866   0.097  1.00  0.00           H  
HETATM   42  H4  UNL     1       6.323   0.046  -1.728  1.00  0.00           H  
HETATM   43  H5  UNL     1       3.764   0.404   0.913  1.00  0.00           H  
HETATM   44  H6  UNL     1       4.282   1.910  -2.813  1.00  0.00           H  
HETATM   45  H7  UNL     1       1.633  -0.003   0.832  1.00  0.00           H  
HETATM   46  H8  UNL     1      -0.893   0.833  -1.688  1.00  0.00           H  
HETATM   47  H9  UNL     1      -2.278  -0.143  -2.344  1.00  0.00           H  
HETATM   48  H10 UNL     1      -1.570   0.928   0.425  1.00  0.00           H  
HETATM   49  H11 UNL     1      -3.545   1.023   1.884  1.00  0.00           H  
HETATM   50  H12 UNL     1      -5.235   2.831   2.427  1.00  0.00           H  
HETATM   51  H13 UNL     1      -9.949   0.084  -1.032  1.00  0.00           H  
HETATM   52  H14 UNL     1      -8.792  -2.449  -1.113  1.00  0.00           H  
HETATM   53  H15 UNL     1      -8.108  -1.825  -2.684  1.00  0.00           H  
HETATM   54  H16 UNL     1      -4.626  -1.186   0.050  1.00  0.00           H  
HETATM   55  H17 UNL     1      -4.538  -2.353   1.932  1.00  0.00           H  
HETATM   56  H18 UNL     1      -2.345  -1.876   0.032  1.00  0.00           H  
HETATM   57  H19 UNL     1      -1.378  -0.033   1.916  1.00  0.00           H  
HETATM   58  H20 UNL     1       4.627  -1.496   1.996  1.00  0.00           H  
HETATM   59  H21 UNL     1       5.987  -2.928   0.459  1.00  0.00           H  
HETATM   60  H22 UNL     1       7.049  -1.898   1.721  1.00  0.00           H  
HETATM   61  H23 UNL     1       7.656   0.253   2.453  1.00  0.00           H  
HETATM   62  H24 UNL     1       7.460  -1.454  -0.477  1.00  0.00           H  
HETATM   63  H25 UNL     1       9.278  -0.639   0.186  1.00  0.00           H  
CONECT    1    2   39   40   41
CONECT    2    3   37   42
CONECT    3    4
CONECT    4    5   33   43
CONECT    5    6
CONECT    6    7    7    8    9
CONECT    8   44
CONECT    9   10
CONECT   10   11   11   12   13
CONECT   12   45
CONECT   13   14
CONECT   14   15   46   47
CONECT   15   16   31   48
CONECT   16   17
CONECT   17   18   29   49
CONECT   18   19   28
CONECT   19   20   20   50
CONECT   20   21
CONECT   21   22   28   28
CONECT   22   23   23   24
CONECT   24   25   51
CONECT   25   26   27   27
CONECT   26   52   53
CONECT   27   28
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   37   60
CONECT   36   61
CONECT   37   38   62
CONECT   38   63
END

HMDB0001095
     RDKit          3D
GDP-L-fucose
 63 66  0  0  0  0  0  0  0  0999 V2000
    7.3952    1.6877   -0.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5063    0.4487   -0.7118 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3870    0.9014   -0.0659 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4822   -0.1527    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656   -0.6055   -0.8668 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9423    0.5659   -1.6377 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.5956    1.7218   -0.7501 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8565    1.0578   -2.9908 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4807   -0.0756   -2.3057 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218   -0.8539   -1.0654 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.4601   -2.0942   -0.5997 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9209    0.2893    0.2924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8952   -1.1290   -1.0934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6031    0.0640   -1.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3968    0.2924   -0.2258 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4234    1.1239   -0.1507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1323    0.7231    1.0165 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4679    1.2040    1.0299 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8672    2.2565    1.7489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1856    2.4925    1.5396 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5784    1.5500    0.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8440    1.3110    0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7866    2.0613    0.4774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0127    0.2590   -0.6448 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9320   -0.5423   -0.9462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2965   -1.7060   -1.7023 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7269   -0.3143   -0.4700 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5247    0.7197    0.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0803   -0.8024    0.9063 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3778   -1.4109    2.0944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5738   -0.9473    0.5807 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9025   -0.8530    1.7829 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1336   -1.2352    1.0409 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1584   -2.4125    0.2731 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5878   -0.9391    1.3884 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6987    0.0043    2.4037 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2975   -0.5400    0.1237 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5387   -0.0321    0.4596 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7475    2.5569   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1723    1.4594   -1.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8570    1.8662    0.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3230    0.0456   -1.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638    0.4042    0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2824    1.9098   -2.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6332   -0.0028    0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8926    0.8330   -1.6880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781   -0.1425   -2.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5699    0.9282    0.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5452    1.0234    1.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2351    2.8312    2.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9489    0.0839   -1.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7921   -2.4487   -1.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1084   -1.8247   -2.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6258   -1.1864    0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5382   -2.3531    1.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3449   -1.8764    0.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3776   -0.0334    1.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6270   -1.4960    1.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9865   -2.9284    0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0486   -1.8982    1.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6558    0.2530    2.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4602   -1.4536   -0.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2783   -0.6388    0.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 17 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
  4 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37  2  1  0
 31 15  1  0
 28 18  1  0
 28 21  2  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  2 42  1  6
  4 43  1  0
  8 44  1  0
 12 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  1
 17 49  1  1
 19 50  1  0
 24 51  1  0
 26 52  1  0
 26 53  1  0
 29 54  1  6
 30 55  1  0
 31 56  1  6
 32 57  1  0
 33 58  1  1
 34 59  1  0
 35 60  1  1
 36 61  1  0
 37 62  1  6
 38 63  1  0
M  END

Synonyms

Value	Source
(6-Deoxy-beta-L-galactopyranosyl) ester	HMDB
GDP Fucose	HMDB
GDP-beta-L-Fucose	HMDB
Guanosine diphosphate fucose	HMDB
Guanosine diphosphofucose	HMDB
Diphosphate fucose, guanosine	HMDB
Diphosphofucose, guanosine	HMDB
Fucose, GDP	HMDB
Fucose, guanosine diphosphate	HMDB
GDP-Fucose	HMDB
GDP-Β-L-fucose	HMDB
Guanosine 5'-diphosphate L-fucose	HMDB
Guanosine 5'-diphospho-fucose	HMDB
Guanosine 5'-diphosphofucose	HMDB
Guanosine 5’-diphosphate L-fucose	HMDB
Guanosine 5’-diphospho-fucose	HMDB
Guanosine 5’-diphosphofucose	HMDB
GDP-L-fucose	HMDB

Molecular Formula

C₁₆H₂₅N₅O₁₅P₂

Average Mass

589.3417

Monoisotopic Mass

589.082238179

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]({[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid

Traditional Name

gdp-L-fucose

CAS Registry Number

15839-70-0

SMILES

C[C@@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=C(N)NC3=O)[C@@H](O)[C@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C16H25N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,7-11,14-15,22-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5+,7+,8+,9+,10+,11-,14+,15?/m0/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

GDP-fucose (CHEBI:17009 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	7.04 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-4.2	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	307.2 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	116.97 m³·mol⁻¹	ChemAxon
Polarizability	48.22 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

Golgi apparatus

Biospecimen Locations

Epidermis
Feces
Fibroblasts
Intestine
Kidney
Neuron
Placenta
Platelet
Prostate
Spleen

Tissue Locations

Epidermis
Fibroblasts
Intestine
Kidney
Neuron
Placenta
Platelet
Prostate
Spleen

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191924	Fucose-1-phosphate guanylyltransferase	Unknown	O14772	Homo sapiens
MMDBp0192125	Galactoside 2-alpha-L-fucosyltransferase 2	Enzyme	Q10981	Homo sapiens
MMDBp0192126	Galactoside 2-alpha-L-fucosyltransferase 1	Enzyme	P19526	Homo sapiens
MMDBp0192543	GDP-L-fucose synthase	Enzyme	Q13630	Homo sapiens
MMDBp0192631	Alpha-(1,3)-fucosyltransferase	Enzyme	Q11128	Homo sapiens
MMDBp0194021	Alpha-(1,3)-fucosyltransferase	Enzyme	Q9Y231	Homo sapiens
MMDBp0194022	Alpha-(1,6)-fucosyltransferase	Enzyme	Q9BYC5	Homo sapiens
MMDBp0196148	Alpha-(1,3)-fucosyltransferase	Enzyme	P51993	Homo sapiens
MMDBp0196287	Alpha-(1,3)-fucosyltransferase	Enzyme	Q11130	Homo sapiens
MMDBp0196810	Galactoside 3(4)-L-fucosyltransferase	Unknown	P21217

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018332	GDP-4-Dehydro-6-deoxy-D-mannose	GDP-L-Fucose	GDP-L-fucose synthase	Synthesis	PathBank	31602464

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	4	Human feces; Human sputum; Human pleural fluid plaque; Human ; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	57	Human feces; Human sputum; Human pleural fluid plaque; Human ; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	114	Human feces; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	13	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	2	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	3	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	8	Human feces; Human	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Epidermis	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0001095

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

34623

Wikipedia Link

Not Available

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sibley CP, Hochberg A, Boime I: Bromo-adenosine stimulates choriogonadotropin production in JAr and cytotrophoblast cells: evidence for effects on two stages of differentiation. Mol Endocrinol. 1991 Apr;5(4):582-6. doi: 10.1210/mend-5-4-582. [PubMed:1922090 ]
Galiegue S, Mary S, Marchand J, Dussossoy D, Carriere D, Carayon P, Bouaboula M, Shire D, Le Fur G, Casellas P: Expression of central and peripheral cannabinoid receptors in human immune tissues and leukocyte subpopulations. Eur J Biochem. 1995 Aug 15;232(1):54-61. doi: 10.1111/j.1432-1033.1995.tb20780.x. [PubMed:7556170 ]
Jakob G, Mair J, Vorderwinkler KP, Judmaier G, Konig P, Zwierzina H, Pichler M, Puschendorf B: Clinical significance of urinary cyclic guanosine monophosphate in diagnosis of heart failure. Clin Chem. 1994 Jan;40(1):96-100. [PubMed:8287551 ]
Sales ME, Sterin-Borda L, de Bracco MM, Rodriguez M, Narbaitz M, Borda E: IgA from HIV+ haemophilic patients triggers intracellular signals coupled to the cholinergic system of the intestine. Clin Exp Immunol. 1997 Nov;110(2):189-95. doi: 10.1111/j.1365-2249.1997.tb08316.x. [PubMed:9367401 ]
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Showing metabocard for GDP-L-Fucose (MMDBc0029554)

MOL for #<Metabolite:0x00007f9253159b80>

3D MOL for #<Metabolite:0x00007f9253159b80>

3D SDF for #<Metabolite:0x00007f9253159b80>

3D-SDF for #<Metabolite:0x00007f9253159b80>

PDB for #<Metabolite:0x00007f9253159b80>

3D PDB for #<Metabolite:0x00007f9253159b80>

SMILES for #<Metabolite:0x00007f9253159b80>

INCHI for #<Metabolite:0x00007f9253159b80>

Structure for #<Metabolite:0x00007f9253159b80>

3D Structure for #<Metabolite:0x00007f9253159b80>