Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:35:07 UTC
Update Date2024-04-30 19:39:35 UTC
Metabolite IDMMDBc0029625
Metabolite Identification
Common NameGDP-4-Dehydro-6-deoxy-D-mannose
DescriptionGDP-4-Dehydro-6-deoxy-D-mannose is an intermediate in fructose and mannose metabolism. GDP-4-Dehydro-6-deoxy-D-mannose is generated by GDP-D-mannose-4,6-dehydratase (GMD). This compound is then converted by the FX protein (GDP-4-keto-6-D-deoxymannose epimerase/GDP-4-keto-6-L-galactose reductase) to GDP-L-fucose. (PMID: 11698403 ). It is also involved in amino sugar and nucleotide sugar metabolism. (KEGG)
Structure
Synonyms
ValueSource
GDP-4-Dehydro-6-deoxy-D-taloseChEBI
GDP-4-Dehydro-D-rhamnoseChEBI
GDP-4-Keto-6-deoxy-D-mannoseChEBI
GDP-4-Keto-6-deoxymannoseChEBI
GDP-4-oxo-6-Deoxy-D-mannoseChEBI
Guanosine 5'-(trihydrogen diphosphate), p'-(6-deoxy-alpha-D-lyxo-hexopyranos-4-ulos-1-yl) esterChEBI
Guanosine diphosphate-4-keto-6-deoxy-D-mannoseChEBI
GDP-4-Dehydro-alpha-D-rhamnoseKegg
GDP-4-Dehydro-6-deoxy-alpha-D-mannoseKegg
Guanosine 5'-(trihydrogen diphosphate), p'-(6-deoxy-a-D-lyxo-hexopyranos-4-ulos-1-yl) esterGenerator
Guanosine 5'-(trihydrogen diphosphate), p'-(6-deoxy-α-D-lyxo-hexopyranos-4-ulos-1-yl) esterGenerator
Guanosine 5'-(trihydrogen diphosphoric acid), p'-(6-deoxy-a-D-lyxo-hexopyranos-4-ulos-1-yl) esterGenerator
Guanosine 5'-(trihydrogen diphosphoric acid), p'-(6-deoxy-alpha-D-lyxo-hexopyranos-4-ulos-1-yl) esterGenerator
Guanosine 5'-(trihydrogen diphosphoric acid), p'-(6-deoxy-α-D-lyxo-hexopyranos-4-ulos-1-yl) esterGenerator
Guanosine diphosphoric acid-4-keto-6-deoxy-D-mannoseGenerator
GDP-4-Dehydro-a-D-rhamnoseGenerator
GDP-4-Dehydro-α-D-rhamnoseGenerator
GDP-4-Dehydro-6-deoxy-a-D-mannoseGenerator
GDP-4-Dehydro-6-deoxy-α-D-mannoseGenerator
GDP-4-Keto-6-D-deoxymannoseHMDB
GDP-4-oxo-6-DeoxymannoseHMDB
Guanosine 5'-diphosphate 4-keto-6-deoxy-D-mannoseHMDB
Guanosine 5’-diphosphate 4-keto-6-deoxy-D-mannoseHMDB
Molecular FormulaC16H23N5O15P2
Average Mass587.3258
Monoisotopic Mass587.066588115
IUPAC Name[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,6R)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy})phosphinic acid
Traditional Namegdp-4-keto-6-deoxymannose
CAS Registry Number18186-48-6
SMILES
[H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])O[C@]([H])(C)C(=O)[C@]([H])(O)[C@]2([H])O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3O)[C@]([H])(O)[C@]1([H])O
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)/t4-,5-,8-,9+,10-,11+,14-,15-/m1/s1
InChI KeyPNHLMHWWFOPQLK-BKUUWRAGSA-N