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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-06-16 16:56:21 UTC
HMDB IDHMDB0001439
Secondary Accession Numbers
  • HMDB01439
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 is a very strong basic compound (based on its pKa). Phosphoribosyl formamidocarboxamide exists in all living species, ranging from bacteria to humans. Within humans, phosphoribosyl formamidocarboxamide participates in a number of enzymatic reactions. In particular, tetrahydrofolic acid and phosphoribosyl formamidocarboxamide can be biosynthesized from 10-formyltetrahydrofolate and AICAR through the action of the enzyme bifunctional purine biosynthesis protein purh. In addition, phosphoribosyl formamidocarboxamide can be biosynthesized from inosinic acid; which is mediated by the enzyme bifunctional purine biosynthesis protein purh. In humans, phosphoribosyl formamidocarboxamide is involved in the metabolic disorder called the lesch-nyhan syndrome (lns) pathway. Outside of the human body, Phosphoribosyl formamidocarboxamide has been detected, but not quantified in, several different foods, such as evergreen huckleberries, oats, italian sweet red peppers, sesbania flowers, and skunk currants. This could make phosphoribosyl formamidocarboxamide a potential biomarker for the consumption of these foods.
Structure
Data?1592326581
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 ribotideHMDB
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 Number13018-54-7
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

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 g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9725000000-466b9ed7af43597f7fffSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-9240300000-b9e749599e4fdfe0510aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ar0-0914000000-1d61e2aa1204766a006eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0900000000-051245189eb5cd0ff26fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-1900000000-f18e08c70bdaa9aa6913Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gdj-8809000000-e71e875c5ef95845f25dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-9700000000-1930562d45d841bd928dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-5b37e0fb5e34ee3423f0Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031113
KNApSAcK IDNot Available
Chemspider ID145893
KEGG Compound IDC04734
BioCyc IDPHOSPHORIBOSYL-FORMAMIDO-CARBOXAMIDE
BiGG ID44434
Wikipedia LinkNot Available
METLIN ID6247
PubChem Compound166760
PDB IDNot Available
ChEBI ID18381
Food Biomarker OntologyNot Available
VMH IDFPRICA
MarkerDB ID
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