Showing Metabocard for 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide (BASm0003483)

Common Name5-formamido-1-(5-phospho-d-ribosyl)imidazole-4-carboxamide
DescriptionThis compound is an intermediate in purine metabolism, where it is the byproduct of phosphoribosylaminoimidazolecarboxamide formyltransferase (EC 2.1.2.3) and IMP cyclohydrolase (EC 3.5.4.10). It is also a byproduct of Ligases (EC 6.3.4.-).
Structure
Molecular FormulaC10H15N4O9P
Average Mass366.22130
Monoisotopic Mass366.05766
IUPAC Name{[(2R,3S,4R,5R)-5-(4-carbamoyl-5-formamido-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2r,3s,4r,5r)-5-(4-carbamoyl-5-formamidoimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
CAS Registry Number13018-54-7
SMILESNC(=O)c1ncn([C@@H]2O[C@H](COP(=O)([O-])[O-])[C@@H](O)[C@H]2O)c1NC=O
InChI IdentifierInChI=1S/C10H15N4O9P/c11-8(18)5-9(13-3-15)14(2-12-5)10-7(17)6(16)4(23-10)1-22-24(19,20)21/h2-4,6-7,10,16-17H,1H2,(H2,11,18)(H,13,15)(H2,19,20,21)/t4-,6-,7-,10-/m1/s1
InChI KeyABCOOORLYAOBOZ-KQYNXXCUSA-N
CHEBI IDCHEBI:58467
HMDB IDHMDB0001439
Pathways
NameSMPDB/PathBank
Purine metabolism
Adenosine Deaminase Deficiency
Adenylosuccinate Lyase Deficiency
AICA-Ribosiduria
Molybdenum Cofactor Deficiency
Purine Nucleoside Phosphorylase Deficiency
Xanthine Dehydrogenase Deficiency (Xanthinuria)
Lesch-Nyhan Syndrome (LNS)
Gout or Kelley-Seegmiller Syndrome
Azathioprine Action Pathway
Mercaptopurine Action Pathway
Thioguanine Action Pathway
Xanthinuria type I
Xanthinuria type II
Adenine phosphoribosyltransferase deficiency (APRT)
Mitochondrial DNA depletion syndrome
Myoadenylate deaminase deficiency
StateSolid
Water Solubility2.14e+00 g/l
logP-1.83
logS-2.23
pKa (Strongest Acidic)1.21
pKa (Strongest Basic)6.25
Hydrogen Acceptor Count9
Hydrogen Donor Count6
Polar Surface Area206.46 Ų
Rotatable Bond Count6
Physiological Charge-2
Formal Charge0
Refractivity74.81 m³·mol⁻¹
Polarizability30.52

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