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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:22:12 UTC
Update Date2020-03-12 16:47:38 UTC
HMDB IDHMDB0012277
Secondary Accession Numbers
  • HMDB12277
Metabolite Identification
Common NamePhosphoribosylformimino-AICAR-P
DescriptionPhosphoribosylformimino-AICAR-P, also known as phosphoribosylformiminoAICAR-phosphate, 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. Phosphoribosylformimino-AICAR-P is a very strong basic compound (based on its pKa). Phosphoribosylformimino-AICAR-P is found in both E. coli and humans.
Structure
Data?1583852546
Synonyms
ValueSource
5'-ProFARChEBI
5-(5-Phospho-D-ribosylaminoformimino)-1-(5-phosphoribosyl)-imidazole-4-carboxamideChEBI
N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamideChEBI
N-(5'-Phosphoribosylformimino)-5-amino-1-(5''-phosphoribosyl)-4-imidazolecarboxamideChEBI
Phosphoribosyl-formimino-aicar-phosphateChEBI
1-(5-Phospho-beta-D-ribosyl)-5-[(5-phospho-beta-D-ribosylamino)methylideneamino]imidazole-4-carboxamideKegg
Phosphoribosyl-formimino-aicar-phosphoric acidGenerator
1-(5-Phospho-b-D-ribosyl)-5-[(5-phospho-b-D-ribosylamino)methylideneamino]imidazole-4-carboxamideGenerator
1-(5-Phospho-β-D-ribosyl)-5-[(5-phospho-β-D-ribosylamino)methylideneamino]imidazole-4-carboxamideGenerator
1-(5-Phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamideChEBI, KEGG
1-(5-O-Phosphono-beta-D-ribofuranosyl)-5-[[[(5-O-phosphono-beta-D-ribofuranosyl)amino]methylene]amino]-1H-imidazole-4-carboxamideHMDB
1-(5-O-Phosphono-β-D-ribofuranosyl)-5-[[[(5-O-phosphono-β-D-ribofuranosyl)amino]methylene]amino]-1H-imidazole-4-carboxamideHMDB
5-(5'-Phospho-D-ribosyl-aminoformimino)-1-(5-phosphoribosyl)-imidazole-4-carboxamideHMDB
5-(5-Phospho-D-ribosyl-aminoformimino)-1-(5-phosphoribosyl)-imidazole4-carboxamideHMDB
5-(5’-Phospho-D-ribosyl-aminoformimino)-1-(5-phosphoribosyl)-imidazole-4-carboxamideHMDB
N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phosphoribosyl)-4-imidazolecarboxamideHMDB
N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phosphoribosyl)-4-imidazolylcarboxamideHMDB
N-(5’-Phospho-D-ribosylformimino)-5-amino-1-(5’’-phospho-D-ribosyl)-4-imidazolecarboxamideHMDB
N-(5’-Phospho-D-ribosylformimino)-5-amino-1-(5’’-phosphoribosyl)-4-imidazolecarboxamideHMDB
N-(5’-Phospho-D-ribosylformimino)-5-amino-1-(5’’-phosphoribosyl)-4-imidazolylcarboxamideHMDB
N-(5’-Phosphoribosylformimino)-5-amino-1-(5’’-phosphoribosyl)-4-imidazolecarboxamideHMDB
N-5-Phosphoribosyl-formimino-5-amino-imidazole-4-carboxamide ribonucleotideHMDB
Phosphoribosyl-formimino-AICAR-PHMDB
PhosphoribosylformiminoAICAR-phosphateHMDB
Chemical FormulaC15H25N5O15P2
Average Molecular Weight577.331
Monoisotopic Molecular Weight577.082238179
IUPAC Name{[(2R,3S,4R,5R)-5-{4-carbamoyl-5-[(E)-({N-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]amino}methylidene)amino]-1H-imidazol-1-yl}-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-5-{4-carbamoyl-5-[(E)-({N-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]amino}methylidene)amino]imidazol-1-yl}-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
CAS Registry Number36244-83-4
SMILES
NC(=O)C1=C(\N=C\N[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C15H25N5O15P2/c16-12(25)7-13(17-3-18-14-10(23)8(21)5(34-14)1-32-36(26,27)28)20(4-19-7)15-11(24)9(22)6(35-15)2-33-37(29,30)31/h3-6,8-11,14-15,21-24H,1-2H2,(H2,16,25)(H,17,18)(H2,26,27,28)(H2,29,30,31)/t5-,6-,8-,9-,10-,11-,14-,15-/m1/s1
InChI KeyQOUSHGMTBIIAHR-KEOHHSTQSA-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
  • 2-heteroaryl carboxamide
  • Imidazole-4-carbonyl group
  • Monoalkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Vinylogous amide
  • Azole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Imidazole
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Oxacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Formamidine
  • Carboxylic acid amidine
  • Carboxylic acid derivative
  • Amidine
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

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 Solubility5.75 g/LALOGPS
logP-1.8ALOGPS
logP-5.5ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.21ChemAxon
pKa (Strongest Basic)6.75ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area318.2 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity114.57 m³·mol⁻¹ChemAxon
Polarizability48.23 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0229130000-77ae7326f3b61ac79629Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxs-0729000000-f68502ca665d560b4babSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0796000000-bf5a600e9f63aa3731fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01tc-6419340000-e587f8a52b28fa93d93eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9303000000-becf2ce868f0d12c63f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a4eaaeca4343c1c85295Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB028909
KNApSAcK IDNot Available
Chemspider ID7827522
KEGG Compound IDC04896
BioCyc IDPHOSPHORIBOSYL-FORMIMINO-AICAR-P
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440534
PDB IDNot Available
ChEBI ID18302
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available