5-Amino-4-imidazolecarboxyamide (PAMDB000946)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000946
Identification
Name: 5-Amino-4-imidazolecarboxyamide
Description:5-Amino-4-imidazolecarboxyamide is a metabolite of purine metabolism. Adenine phosphoribosyltransferase [EC:2.4.2.7] catalyzes both the formation of 5-Amino-4-imidazolecarboxyamide and its conversion to 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide, also called AICAR. (KEGG)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 1H-Imidazole-4-carboxamide, 5-amino-, monohydrochloride
  • 360-97-4 (FREE BASE)
  • 4-Amino-1H-imidazole-5-carboxamide
  • 4-Amino-5-carboxamido imidazole hydrochloride
  • 4-Amino-5-imidazole carboxamide
  • 4-Amino-5-Imidazolecarboxamide
  • 4-Amino-5-imidazolecarboxamide hydrochloride
  • 4-Aminoimidazole-5-carboxamide
  • 4-Aminoimidazole-5-carboxamide hydrochoride
  • 4-Carbamoyl-5-aminoimidazole
  • 4-Carboxamido-5-aminoimidazole
  • 5'-P-Ribosyl-5-amino-4-imidazole carboxamide
  • 5'-Phosphoribosyl-5-amino-4-imidazole carboxamide
  • 5(OR 4)-AMINO-IMIDAZOLE-4(OR 5)-CARBOXAMIDE
  • 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
  • 5-Amino-1H-Imidazole-4-carboxamide
  • 5-Amino-4-imidazolecarboxamide
  • 5-Amino-4-imidazolecarboxamide ribotide
  • 5-Amino-Imidazole-4-carboxamide
  • 5-Aminoimidazol-4-carboxamide
  • 5-Aminoimidazol-4-carboxamide, hydrochloride
  • 5-Aminoimidazole carboxamide
  • 5-Aminoimidazole-4-carboxamide
  • 5-Aminoimidazole-4-carboxamide hydrochloride
  • 5-Aminoimidazole-4-carboxamide ribotide
  • 5-Aminoimidazolecarboxamide
  • 5-Imidazolecarboxamide, 4-amino-, hydrochloride
  • AIC
  • Aic .cntdot. HCL
  • AICA
  • AICA ribonucleotide
  • Aicar
  • Aminoimidazole carboxamide
  • Colahepat
  • Diazol-c
  • Imidazole C-4,5 deriv. 2
  • Imidazole-4-carboxamide, 5-amino-, monohydrochloride
  • WLN: T5M CNJ DVZ EZ
  • Z-Nucleotide
Chemical Formula: C4H6N4O
Average Molecular Weight: 126.1166
Monoisotopic Molecular Weight: 126.054160834
InChI Key: DVNYTAVYBRSTGK-UHFFFAOYSA-N
InChI:InChI=1S/C4H6N4O/c5-3-2(4(6)9)7-1-8-3/h1H,5H2,(H2,6,9)(H,7,8)
CAS number: 72-40-2
IUPAC Name:4-amino-1H-imidazole-5-carboxamide
Traditional IUPAC Name: 4-aminoimidazole-5-carboxamide
SMILES:NC(=O)C1=C(N)N=CN1
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as aminoimidazoles. These are organic compounds containing an amino group linked to an imidazole ring.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Azoles
Sub ClassImidazoles
Direct Parent Aminoimidazoles
Alternative Parents
Substituents
  • Imidolactam
  • Primary aromatic amine
  • Aminoimidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Primary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility124.0 mg/mLALOGPS
logP-1.2ALOGPS
logP-0.96ChemAxon
logS-0.01ALOGPS
pKa (Strongest Acidic)12.74ChemAxon
pKa (Strongest Basic)5.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area97.79 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.98 m3·mol-1ChemAxon
Polarizability11.37 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
AICAR + Pyrophosphate <> 5-Amino-4-imidazolecarboxyamide + Phosphoribosyl pyrophosphate
Phosphoribulosylformimino-AICAR-P + L-Glutamine > L-Glutamic acid + Hydrogen ion + 5-Amino-4-imidazolecarboxyamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0f9i-4965000000-81d31245e06d3f90edafView in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0kgk-3936100000-5d3d51d18ff3e42df0e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-5ac6303648d30c83dd8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-5900000000-891e8af2ee696c82bb67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-d969e00c4e0a26137fb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-5900000000-38872de2bfb260a5d96fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0563-9400000000-5d37f6e245dbc41ac3e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-9797d793034ec5f4f97fView in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID18406
HMDB IDHMDB03192
Pubchem Compound ID9679
Kegg IDC04051
ChemSpider ID9298
Wikipedia IDNot Available
BioCyc IDAICAR
EcoCyc IDAICAR
Ligand Expo5AC