Showing metabocard for Phosphoribosyl formamidocarboxamide (BMDB0001439)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:45:58 UTC
Update Date2020-05-19 22:01:26 UTC
BMDB IDBMDB0001439
Secondary Accession Numbers
  • BMDB01439
Metabolite Identification
Common NamePhosphoribosyl formamidocarboxamide
DescriptionPhosphoribosyl formamidocarboxamide, also known as FAICAR, belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond. Phosphoribosyl formamidocarboxamide exists in all living species, ranging from bacteria to plants to humans. Based on a literature review very few articles have been published on Phosphoribosyl formamidocarboxamide.
Structure
Thumb
MOLSDFPDBSMILESInChI
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-Formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamideKegg
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-Phosphoribosyl)-imidazole-4-carboxamideHMDB
5-Phosphoribosyl-5-formamido-4-imid-carboxamideHMDB
Phosphoribosyl-formamido-carboxamideHMDB
5-Formamidoimidazole-4-carboxamide ribotideMeSH, HMDB
5-(Formylamino)-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazole-4-carboxamideHMDB
5-(Formylamino)-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazole-4-carboxamideHMDB
5-Formylamino-4-imidazolecarboxamide ribonucleotideHMDB
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
Description belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassImidazole ribonucleosides and ribonucleotides
Sub Class1-ribosyl-imidazolecarboxamides
Direct Parent1-ribosyl-imidazolecarboxamides
Alternative Parents
Substituents
  • 1-ribosyl-imidazolecarboxamide
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • N-arylamide
  • 2-heteroaryl carboxamide
  • Imidazole-4-carbonyl group
  • Monoalkyl phosphate
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Alkyl phosphate
  • Phosphoric acid ester
  • Heteroaromatic compound
  • Azole
  • Vinylogous amide
  • Imidazole
  • Tetrahydrofuran
  • Carboxamide group
  • 1,2-diol
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity74.81 m³·mol⁻¹ChemAxon
Polarizability30.52 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001439
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022622
KNApSAcK IDNot Available
Chemspider ID145893
KEGG Compound IDC04734
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound166760
PDB IDNot Available
ChEBI ID18381
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Bifunctional purine biosynthesis protein PURH
General function:
Nucleotide transport and metabolism
Specific function:
Bifunctional enzyme that catalyzes 2 steps in purine biosynthesis.
Gene Name:
ATIC
Uniprot ID:
Q0VCK0
Molecular weight:
64483.0
Reactions
N10-Formyl-THF + AICAR → Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamidedetails
Inosinic acid + Water → Phosphoribosyl formamidocarboxamidedetails
Enzyme Details
2. Adenylosuccinate lyase
General function:
Nucleotide transport and metabolism
Specific function:
Catalyzes two non-sequential steps in de novo AMP synthesis: converts (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate (SAICAR) to fumarate plus 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide, and thereby also contributes to de novo IMP synthesis, and converts succinyladenosine monophosphate (SAMP) to AMP and fumarate.
Gene Name:
ADSL
Uniprot ID:
A3KN12
Molecular weight:
55484.0