Record Information
Version2.0
Creation Date2015-09-08 17:49:58 -0600
Update Date2015-09-14 16:46:04 -0600
Secondary Accession Numbers
  • ECMDB24188
Identification
Name:FAICAR
DescriptionPhosphoribosyl formamidocarboxamide (FAICAR) 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:Not Available
Chemical Formula:C10H15N4O9P
Weight:Average: 366.223
Monoisotopic: 366.057665077
InChI Key:XUHZFJMJICUKLB-UHFFFAOYSA-N
InChI:InChI=1S/C10H15N4O9P/c11-9(18)6-4(12-3-15)1-14(13-6)10-8(17)7(16)5(23-10)2-22-24(19,20)21/h1,3,5,7-8,10,16-17H,2H2,(H2,11,18)(H,12,15)(H2,19,20,21)
CAS number:Not Available
IUPAC Name:{[5-(3-carbamoyl-4-formamido-1H-pyrazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:[5-(3-carbamoyl-4-formamidopyrazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
SMILES:[H]C(=O)NC1=CN(N=C1C(N)=O)C1OC(COP(O)(O)=O)C(O)C1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose-5-phosphate
  • Pentose phosphate
  • 1-ribofuranosylpyrazole
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • 2-heteroaryl carboxamide
  • Pyrazole-5-carboxamide
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Pyrazole
  • Azole
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.14 g/LALOGPS
logP-1.7ALOGPS
logP-2.6ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-0.46ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area206.46 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity86.61 m³·mol⁻¹ChemAxon
Polarizability31.23 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
One Carbon Pool by Folate IPW001735 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesisPW000910 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesis 1435709748PW000960 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesis 2PW002033 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_18) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-1927000000-87bc2d469039bc9f05a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0c2j-2922000000-0299f534a9f714f2d251View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08mi-4910000000-cb9a0ee853ef5018c8e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1901000000-b2be67be129148f4164bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-c7fa5890f5465e7f58f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-0d5c63d4bfe219c98c0dView in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia ID5-Formamidoimidazole-4-carboxamide ribotide
BioCyc IDNot Available

Enzymes

General function:
Involved in IMP cyclohydrolase activity
Specific function:
10-formyltetrahydrofolate + 5-amino-1-(5- phospho-D-ribosyl)imidazole-4-carboxamide = tetrahydrofolate + 5- formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
Gene Name:
purH
Uniprot ID:
P15639
Molecular weight:
57329
Reactions
10-formyltetrahydrofolate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide = tetrahydrofolate + 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.
IMP + H(2)O = 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.