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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9725000000-466b9ed7af43597f7fffView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-9240300000-b9e749599e4fdfe0510aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016u-9007000000-60a18b9e82325eba8d6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9002000000-45c1e86e798b498a86e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-681d7ff850cbe4448fe9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0819000000-600f59ce04e9f2036927View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-1922000000-ab410f3897dc2f486680View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-4900000000-cd0a95ff69a87468beebView in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
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