MiMeDB: Showing metabocard for GDP-4-Oxo-L-fucose (MMDBc0031613)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:41:25 UTC

Update Date

2022-08-31 18:22:29 UTC

Metabolite ID

MMDBc0031613

Metabolite Identification

Common Name

GDP-4-Oxo-L-fucose

Description

GDP-4-oxo-L-fucose is a member of the chemical class known as Purine Nucleotide Sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Structure

MOL SDF PDB SMILES InChI

46173240
  Mrv0541 07101213292D          

 59 62  0  0  1  0            999 V2000
    8.1496    1.1943    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.5710    1.3411    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.0585   -0.2614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9646    0.1547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0221    1.6050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4813    0.7105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9076    2.3087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3241    1.0043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8303    0.3306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8179    1.6781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1669    1.2982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9973    2.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6334    0.5259    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.6658    1.8626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -3.6132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9078    2.0943    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.2341    0.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171   -1.2992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.1381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171   -2.6270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.3756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -1.1381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7896    0.1533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2757    0.8199    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2734   -0.5150    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0599    0.5636    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7282    1.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -1.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4986   -1.9631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -2.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7455    1.1512    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9924    1.4881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4137    1.6350    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5759    2.7925    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3289    2.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4910    3.6132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5582    0.6094    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7706    0.9008    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7681   -0.5942    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5153    0.3306    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0149    1.4709    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3609    1.4033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7096    0.5981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3651    1.9845    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0101   -1.9631    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3312    0.8512    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5255    1.6970    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4664    1.1262    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1089    3.0014    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.6266    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9998    3.6657    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4384    4.1219    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9823    3.5606    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2973    0.1217    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5812    1.5981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.3939    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.6266    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 10  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  2  0  0  0  0
  2  8  1  0  0  0  0
  2 10  1  0  0  0  0
  2 16  1  0  0  0  0
  2 17  2  0  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
 23  4  1  6  0  0  0
  4 45  1  0  0  0  0
 24  5  1  6  0  0  0
  5 46  1  0  0  0  0
  6 27  1  0  0  0  0
  7 32  1  0  0  0  0
  7 34  1  0  0  0  0
  8 32  1  0  0  0  0
 31  9  1  6  0  0  0
  9 56  1  0  0  0  0
 33 11  1  1  0  0  0
 11 57  1  0  0  0  0
 12 35  2  0  0  0  0
 15 36  2  0  0  0  0
 25 18  1  1  0  0  0
 18 28  1  0  0  0  0
 18 29  1  0  0  0  0
 19 28  1  0  0  0  0
 19 38  1  0  0  0  0
 19 52  1  0  0  0  0
 20 29  2  0  0  0  0
 20 30  1  0  0  0  0
 21 36  1  0  0  0  0
 21 38  2  0  0  0  0
 22 38  1  0  0  0  0
 22 58  1  0  0  0  0
 22 59  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 39  1  0  0  0  0
 24 26  1  0  0  0  0
 24 40  1  0  0  0  0
 25 41  1  0  0  0  0
 26 27  1  1  0  0  0
 26 42  1  0  0  0  0
 27 43  1  0  0  0  0
 27 44  1  0  0  0  0
 28 30  2  0  0  0  0
 29 47  1  0  0  0  0
 30 36  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 48  1  0  0  0  0
 32 49  1  0  0  0  0
 33 35  1  0  0  0  0
 33 50  1  0  0  0  0
 34 35  1  0  0  0  0
 34 37  1  1  0  0  0
 34 51  1  0  0  0  0
 37 53  1  0  0  0  0
 37 54  1  0  0  0  0
 37 55  1  0  0  0  0
M  CHG  2  13  -1  16  -1
M  END

46173240
  Mrv0541 07101213292D          

 59 62  0  0  1  0            999 V2000
    8.1496    1.1943    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.5710    1.3411    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.0585   -0.2614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9646    0.1547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0221    1.6050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4813    0.7105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9076    2.3087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3241    1.0043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8303    0.3306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8179    1.6781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1669    1.2982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9973    2.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6334    0.5259    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.6658    1.8626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -3.6132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9078    2.0943    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.2341    0.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171   -1.2992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.1381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171   -2.6270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.3756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -1.1381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7896    0.1533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2757    0.8199    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2734   -0.5150    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0599    0.5636    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7282    1.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -1.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4986   -1.9631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -2.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7455    1.1512    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9924    1.4881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4137    1.6350    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5759    2.7925    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3289    2.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4910    3.6132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5582    0.6094    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7706    0.9008    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7681   -0.5942    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5153    0.3306    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0149    1.4709    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3609    1.4033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7096    0.5981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3651    1.9845    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0101   -1.9631    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3312    0.8512    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5255    1.6970    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4664    1.1262    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1089    3.0014    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.6266    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9998    3.6657    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4384    4.1219    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9823    3.5606    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2973    0.1217    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5812    1.5981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.3939    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.6266    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 10  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  2  0  0  0  0
  2  8  1  0  0  0  0
  2 10  1  0  0  0  0
  2 16  1  0  0  0  0
  2 17  2  0  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
 23  4  1  6  0  0  0
  4 45  1  0  0  0  0
 24  5  1  6  0  0  0
  5 46  1  0  0  0  0
  6 27  1  0  0  0  0
  7 32  1  0  0  0  0
  7 34  1  0  0  0  0
  8 32  1  0  0  0  0
 31  9  1  6  0  0  0
  9 56  1  0  0  0  0
 33 11  1  1  0  0  0
 11 57  1  0  0  0  0
 12 35  2  0  0  0  0
 15 36  2  0  0  0  0
 25 18  1  1  0  0  0
 18 28  1  0  0  0  0
 18 29  1  0  0  0  0
 19 28  1  0  0  0  0
 19 38  1  0  0  0  0
 19 52  1  0  0  0  0
 20 29  2  0  0  0  0
 20 30  1  0  0  0  0
 21 36  1  0  0  0  0
 21 38  2  0  0  0  0
 22 38  1  0  0  0  0
 22 58  1  0  0  0  0
 22 59  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 39  1  0  0  0  0
 24 26  1  0  0  0  0
 24 40  1  0  0  0  0
 25 41  1  0  0  0  0
 26 27  1  1  0  0  0
 26 42  1  0  0  0  0
 27 43  1  0  0  0  0
 27 44  1  0  0  0  0
 28 30  2  0  0  0  0
 29 47  1  0  0  0  0
 30 36  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 48  1  0  0  0  0
 32 49  1  0  0  0  0
 33 35  1  0  0  0  0
 33 50  1  0  0  0  0
 34 35  1  0  0  0  0
 34 37  1  1  0  0  0
 34 51  1  0  0  0  0
 37 53  1  0  0  0  0
 37 54  1  0  0  0  0
 37 55  1  0  0  0  0
M  CHG  2  13  -1  16  -1
M  END
> <DATABASE_ID>
MMDBc0031613

> <DATABASE_NAME>
MIME

> <SMILES>
[H]O[C@@]1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP([O-])(=O)OP([O-])(=O)OC2([H])O[C@]([H])(C(=O)[C@@]([H])(O[H])[C@]2([H])O[H])C([H])([H])[H])[C@@]1([H])O[H])N1C([H])=NC2=C1N([H])C(=NC2=O)N([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H23N5O15P2/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/h3-5,8-11,14-15,23-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/p-2/t4-,5+,8+,9+,10+,11-,14+,15?/m0/s1

> <INCHI_KEY>
PNHLMHWWFOPQLK-WAMCPPDZSA-L

> <FORMULA>
C16H21N5O15P2

> <MOLECULAR_WEIGHT>
585.31

> <EXACT_MASS>
585.050938051

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
48.38860902962003

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3S,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl phosphonato]oxy}phosphonate

> <ALOGPS_LOGP>
-0.95

> <JCHEM_LOGP>
-4.1374417096187095

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.2592208205302975

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.542091372933819

> <JCHEM_PKA_STRONGEST_BASIC>
1.6752574656936854

> <JCHEM_POLAR_SURFACE_AREA>
309.7

> <JCHEM_REFRACTIVITY>
113.52409999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.83e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [(3S,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl phosphonato]oxyphosphonate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-JUL-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 46173240                                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-JUL-12         0                                  
HETATM    1  P   UNK     0      15.213   2.229   0.000  0.00  0.00           P+0
HETATM    2  P   UNK     0      17.866   2.503   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0      11.309  -0.488   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.401   0.289   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.375   2.996   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      13.965   1.326   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      20.361   4.310   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      19.272   1.875   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      22.083   0.617   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      16.460   3.132   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      24.578   2.423   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      24.262   5.487   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      16.116   0.982   0.000  0.00  0.00           O-1
HETATM   14  O   UNK     0      14.309   3.477   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.574  -6.745   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      18.495   3.909   0.000  0.00  0.00           O-1
HETATM   17  O   UNK     0      17.237   1.098   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0       9.365  -2.425   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       6.574  -2.124   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       9.365  -4.904   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       5.241  -4.435   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       3.907  -2.124   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       8.941   0.286   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.848   1.530   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.844  -0.961   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.312   1.052   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.559   1.955   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.908  -2.894   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.264  -3.664   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.908  -4.435   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      21.925   2.149   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      20.519   2.778   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      23.172   3.052   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      21.608   5.213   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      23.014   4.584   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.574  -5.205   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      21.450   6.745   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.241  -2.894   0.000  0.00  0.00           C+0
HETATM   39  H   UNK     0       8.509   1.138   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0       8.905   1.681   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0       8.900  -1.109   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0      12.162   0.617   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0      13.095   2.746   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0      11.874   2.620   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0       6.925   1.117   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      10.015   3.704   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      11.219  -3.664   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      21.152   1.589   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0      19.648   3.168   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0      23.271   2.102   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0      20.737   5.603   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0       6.574  -1.170   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0      22.400   6.843   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0      21.352   7.694   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0      20.500   6.646   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0      22.955   0.227   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0      25.352   2.983   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.080  -2.602   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.907  -1.170   0.000  0.00  0.00           H+0
CONECT    1    6   10   13   14                                             
CONECT    2    8   10   16   17                                             
CONECT    3   25   26                                                       
CONECT    4   23   45                                                       
CONECT    5   24   46                                                       
CONECT    6    1   27                                                       
CONECT    7   32   34                                                       
CONECT    8    2   32                                                       
CONECT    9   31   56                                                       
CONECT   10    1    2                                                       
CONECT   11   33   57                                                       
CONECT   12   35                                                            
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15   36                                                            
CONECT   16    2                                                            
CONECT   17    2                                                            
CONECT   18   25   28   29                                                  
CONECT   19   28   38   52                                                  
CONECT   20   29   30                                                       
CONECT   21   36   38                                                       
CONECT   22   38   58   59                                                  
CONECT   23    4   24   25   39                                             
CONECT   24    5   23   26   40                                             
CONECT   25    3   18   23   41                                             
CONECT   26    3   24   27   42                                             
CONECT   27    6   26   43   44                                             
CONECT   28   18   19   30                                                  
CONECT   29   18   20   47                                                  
CONECT   30   20   28   36                                                  
CONECT   31    9   32   33   48                                             
CONECT   32    7    8   31   49                                             
CONECT   33   11   31   35   50                                             
CONECT   34    7   35   37   51                                             
CONECT   35   12   33   34                                                  
CONECT   36   15   21   30                                                  
CONECT   37   34   53   54   55                                             
CONECT   38   19   21   22                                                  
CONECT   39   23                                                            
CONECT   40   24                                                            
CONECT   41   25                                                            
CONECT   42   26                                                            
CONECT   43   27                                                            
CONECT   44   27                                                            
CONECT   45    4                                                            
CONECT   46    5                                                            
CONECT   47   29                                                            
CONECT   48   31                                                            
CONECT   49   32                                                            
CONECT   50   33                                                            
CONECT   51   34                                                            
CONECT   52   19                                                            
CONECT   53   37                                                            
CONECT   54   37                                                            
CONECT   55   37                                                            
CONECT   56    9                                                            
CONECT   57   11                                                            
CONECT   58   22                                                            
CONECT   59   22                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  124    0
END

Synonyms

Value	Source
9-[(2R,3R,4S,5R)-5-{[({[(3S,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-2-imino-3,9-dihydro-2H-purin-6-olic acid	Generator

Molecular Formula

C₁₆H₂₁N₅O₁₅P₂

Average Mass

585.31

Monoisotopic Mass

585.050938051

IUPAC Name

[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3S,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl phosphonato]oxy}phosphonate

Traditional Name

[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [(3S,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl phosphonato]oxyphosphonate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP([O-])(=O)OP([O-])(=O)OC2([H])O[C@]([H])(C(=O)[C@@]([H])(O[H])[C@]2([H])O[H])C([H])([H])[H])[C@@]1([H])O[H])N1C([H])=NC2=C1N([H])C(=NC2=O)N([H])[H]

InChI Identifier

InChI=1S/C16H23N5O15P2/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/h3-5,8-11,14-15,23-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/p-2/t4-,5+,8+,9+,10+,11-,14+,15?/m0/s1

InChI Key

PNHLMHWWFOPQLK-WAMCPPDZSA-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-5-phosphate
Pentose phosphate
N-glycosyl compound
Glycosyl compound
Organic pyrophosphate
Monosaccharide phosphate
Hypoxanthine
6-oxopurine
Purine
Imidazopyrimidine
Pyrimidone
Aminopyrimidine
Alkyl phosphate
Pyrimidine
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
N-substituted imidazole
Monosaccharide
Heteroaromatic compound
Vinylogous amide
Tetrahydrofuran
Imidazole
Azole
Cyclic ketone
Secondary alcohol
Ketone
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	6.83 g/L	ALOGPS
logP	-0.95	ALOGPS
logP	-4.1	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	2.54	ChemAxon
pKa (Strongest Basic)	1.68	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	309.7 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	113.52 m³·mol⁻¹	ChemAxon
Polarizability	48.39 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0200090000-63731f453f9fe730872d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00lr-0121090000-ce0277aca6d4031f71c0	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9400000000-0c3578e30354ce3381d9	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-3200090000-3d8eb9f14992876ae999	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-8710090000-7174b0a35c72a2bdae67	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0avi-9200000000-48d202975eff6b7c9db4	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

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	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45479378

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sajed T, Marcu A, Ramirez M, Pon A, Guo AC, Knox C, Wilson M, Grant JR, Djoumbou Y, Wishart DS: ECMDB 2.0: A richer resource for understanding the biochemistry of E. coli. Nucleic Acids Res. 2016 Jan 4;44(D1):D495-501. doi: 10.1093/nar/gkv1060. Epub 2015 Oct 19. [PubMed:26481353 ]

Showing metabocard for GDP-4-Oxo-L-fucose (MMDBc0031613)

MOL for #<Metabolite:0x00007f46d8b23f10>

3D MOL for #<Metabolite:0x00007f46d8b23f10>

3D SDF for #<Metabolite:0x00007f46d8b23f10>

3D-SDF for #<Metabolite:0x00007f46d8b23f10>

PDB for #<Metabolite:0x00007f46d8b23f10>

3D PDB for #<Metabolite:0x00007f46d8b23f10>

SMILES for #<Metabolite:0x00007f46d8b23f10>

INCHI for #<Metabolite:0x00007f46d8b23f10>

Structure for #<Metabolite:0x00007f46d8b23f10>

3D Structure for #<Metabolite:0x00007f46d8b23f10>