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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-25 16:45:59 UTC
HMDB IDHMDB0001439
Secondary Accession Numbers
  • HMDB01439
StatusExpected but not Quantified
Metabolite Identification
Common NamePhosphoribosyl formamidocarboxamide
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
Thumb
Synonyms
ValueSource
1-(5'-Phosphoribosyl)-5-formamido-4-imidazolecarboxamideChEBI
5'-Phosphoribosyl-5-formamido-4-imidazolecarboxamideChEBI
5-formamido-1-(5-Phosphoribosyl)imidazole-4-carboxamideChEBI
FAICARChEBI
5'-P-Ribosyl-5-formamido-4-imidazole carboxamideHMDB
5'-Phosphoribosyl-5-formamido-4-imidazole carboxamideHMDB
5-amino-1-(5-phospho-D-Ribosyl)imidazole-4-carboxamideHMDB
5-formamido-1-(5-phospho-D-Ribosyl)imidazole-4-carboxamideHMDB
5-formamido-1-(5-Phosphoribosyl)-imidazole-4-carboxamideHMDB
5-Phosphoribosyl-5-formamido-4-imid-carboxamideHMDB
Phosphoribosyl-formamido-carboxamideHMDB
5-Formamidoimidazole-4-carboxamide ribotideMeSH
Chemical FormulaC10H15N4O9P
Average Molecular Weight366.2213
Monoisotopic Molecular Weight366.05766461
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 NumberNot Available
SMILES
NC(=O)C1=C(NC=O)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=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
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassImidazole ribonucleosides and ribonucleotides
Direct Parent1-ribosyl-imidazolecarboxamides
Alternative Parents
Substituents
  • 1-ribosyl-imidazolecarboxamide
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • 2-heteroaryl carboxamide
  • N-arylamide
  • Imidazole-4-carbonyl group
  • Monoalkyl phosphate
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Alkyl phosphate
  • Phosphoric acid ester
  • Azole
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Vinylogous amide
  • 1,2-diol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition
Biological Location:
Source:
Subcellular:
Process
Naturally occurring process:
Biological process:
Biochemical pathway:
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.14 mg/mLALOGPS
logP-1.8ALOGPS
logP-4.1ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.21ChemAxon
pKa (Strongest Basic)6.25ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area206.46 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity74.81 m3·mol-1ChemAxon
Polarizability30.52 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ar0-0914000000-1d61e2aa1204766a006eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0900000000-051245189eb5cd0ff26fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-1900000000-f18e08c70bdaa9aa6913View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gdj-8809000000-e71e875c5ef95845f25dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-9700000000-1930562d45d841bd928dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-5b37e0fb5e34ee3423f0View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
AICA-RibosiduriaPw000082Pw000082 greyscalePw000082 simpleNot Available
Adenine phosphoribosyltransferase deficiency (APRT)Pw000511Pw000511 greyscalePw000511 simpleNot Available
Adenosine Deaminase DeficiencyPw000075Pw000075 greyscalePw000075 simpleNot Available
Adenylosuccinate Lyase DeficiencyPw000076Pw000076 greyscalePw000076 simpleNot Available
Azathioprine PathwayPw000266Pw000266 greyscalePw000266 simpleNot Available
Displaying entries 1 - 5 of 17 in total
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022622
KNApSAcK IDNot Available
Chemspider ID145893
KEGG Compound IDC04734
BioCyc IDPHOSPHORIBOSYL-FORMAMIDO-CARBOXAMIDE
BiGG ID44434
Wikipedia LinkNot Available
NuGOwiki LinkHMDB0001439
METLIN ID6247
PubChem Compound166760
PDB IDFAI
ChEBI ID18381
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in calcium ion binding
Specific function:
Calcium-dependent nucleotidase with a preference for UDP. The order of activity with different substrates is UDP > GDP > UTP > GTP. Has very low activity towards ADP and even lower activity towards ATP. Does not hydrolyze AMP and GMP. Involved in proteoglycan synthesis.
Gene Name:
CANT1
Uniprot ID:
Q8WVQ1
Molecular weight:
44839.24
General function:
Involved in hydrolase activity
Specific function:
Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) and xanthosine 5'-triphosphate (XTP) to their respective monophosphate derivatives. The enzyme does not distinguish between the deoxy- and ribose forms. Probably excludes non-canonical purines from RNA and DNA precursor pools, thus preventing their incorporation into RNA and DNA and avoiding chromosomal lesions.
Gene Name:
ITPA
Uniprot ID:
Q9BY32
Molecular weight:
16833.23
General function:
Involved in IMP cyclohydrolase activity
Specific function:
Bifunctional enzyme that catalyzes 2 steps in purine biosynthesis.
Gene Name:
ATIC
Uniprot ID:
P31939
Molecular weight:
64615.255
Reactions
10-Formyltetrahydrofolate + AICAR → Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamidedetails
Inosinic acid + Water → Phosphoribosyl formamidocarboxamidedetails