5-Aminoimidazole-4-carboxamide (CHEM003232)

Record Information
Version1.0
Creation Date2014-08-29 06:11:29 UTC
Update Date2026-05-14 18:18:05 UTC
Accession NumberCHEM003232
Identification
Common Name5-Aminoimidazole-4-carboxamide
ClassSmall Molecule
Description
5-Aminoimidazole-4-carboxamide is an imidazole derivative which is a metabolite of the antineoplastic agents BIC and DIC. By itself, or as the ribonucleotide, it is used as a condensation agent in the preparation of nucleosides and nucleotides. Compounded with orotic acid, it is used to treat liver diseases.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • T3DB toxins
Contaminant Type
  • Amine
  • Animal Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-Amino-5-carbamoylimidazoleChEBI
4-Amino-5-imidazolecarboxamideChEBI
5(4)-Amino-4(5)-imidazolecarboxamideChEBI
5-Amino-4-imidazolecarboxyamideChEBI
4-Aminoimidazole-5-carboxamideHMDB
4-Carbamoyl-5-aminoimidazoleHMDB
4-Carboxamido-5-aminoimidazoleHMDB
5-Amino-1H-imidazole-4-carboxamideHMDB
5-Amino-4-imidazolecarboxamideHMDB
5-Amino-imidazole-4-carboxamideHMDB
5-Aminoimidazol-4-carboxamideHMDB
5-Aminoimidazole-4-carboxamide ribotideHMDB
AICHMDB
AICAHMDB
AICARHMDB
ColahepatHMDB
Aminoimidazole carboxamideHMDB
Carboxamide, aminoimidazoleHMDB
Chemical FormulaC4H6N4O
Average Molecular Mass126.117 g/mol
Monoisotopic Mass126.054 g/mol
CAS Registry Number360-97-4
IUPAC Name4-amino-1H-imidazole-5-carboxamide
Traditional Name4-aminoimidazole-5-carboxamide
SMILESNC(=O)C1=C(N)N=CN1
InChI IdentifierInChI=1S/C4H6N4O/c5-3-2(4(6)9)7-1-8-3/h1H,5H2,(H2,6,9)(H,7,8)
InChI KeyDVNYTAVYBRSTGK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminoimidazoles. These are organic compounds containing an amino group linked to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentAminoimidazoles
Alternative Parents
Substituents
  • Aminoimidazole
  • Heteroaromatic compound
  • Azacycle
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Fibroblasts
  • Muscle
  • Platelet
  • Skeletal Muscle
Pathways
NameSMPDB LinkKEGG Link
AICA-RibosiduriaSMP00168 Not Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility124 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.98 m³·mol⁻¹ChemAxon
Polarizability11.37 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0003192
FooDB IDFDB023121
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-3762
METLIN ID629
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID9298
ChEBI ID2030
PubChem Compound ID9679
Kegg Compound IDC04051
YMDB IDNot Available
ECMDB IDECMDB20098
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. Zheng D, MacLean PS, Pohnert SC, Knight JB, Olson AL, Winder WW, Dohm GL: Regulation of muscle GLUT-4 transcription by AMP-activated protein kinase. J Appl Physiol (1985). 2001 Sep;91(3):1073-83.
2. Al-Khalili L, Krook A, Zierath JR, Cartee GD: Prior serum- and AICAR-induced AMPK activation in primary human myocytes does not lead to subsequent increase in insulin-stimulated glucose uptake. Am J Physiol Endocrinol Metab. 2004 Sep;287(3):E553-7. Epub 2004 May 18.
3. Nakano M, Hamada T, Hayashi T, Yonemitsu S, Miyamoto L, Toyoda T, Tanaka S, Masuzaki H, Ebihara K, Ogawa Y, Hosoda K, Inoue G, Yoshimasa Y, Otaka A, Fushiki T, Nakao K: alpha2 isoform-specific activation of 5'adenosine monophosphate-activated protein kinase by 5-aminoimidazole-4-carboxamide-1-beta-D-ribonucleoside at a physiological level activates glucose transport and increases glucose transporter 4 in mouse skeletal muscle. Metabolism. 2006 Mar;55(3):300-8.
4. Fiore D, Jackson AJ, Didolkar MS, Dandu VR: Simultaneous determination of dacarbazine, its photolytic degradation product, 2-azahypoxanthine, and the metabolite 5-aminoimidazole-4-carboxamide in plasma and urine by high-pressure liquid chromatography. Antimicrob Agents Chemother. 1985 Jun;27(6):977-9.
5. Jakobsen SN, Hardie DG, Morrice N, Tornqvist HE: 5'-AMP-activated protein kinase phosphorylates IRS-1 on Ser-789 in mouse C2C12 myotubes in response to 5-aminoimidazole-4-carboxamide riboside. J Biol Chem. 2001 Dec 14;276(50):46912-6. Epub 2001 Oct 11.
6. Lower GM Jr, Lanphear SP, Johnson BM, Bryan GT: Aryl and heterocyclic diazo compounds as potential environmental electrophiles. J Toxicol Environ Health. 1977 May;2(5):1095-107.
7. Wang W, Yang X, Lopez de Silanes I, Carling D, Gorospe M: Increased AMP:ATP ratio and AMP-activated protein kinase activity during cellular senescence linked to reduced HuR function. J Biol Chem. 2003 Jul 18;278(29):27016-23. Epub 2003 May 1.
8. Shang J, Lehrman MA: Activation of glycogen phosphorylase with 5-aminoimidazole-4-carboxamide riboside (AICAR). Assessment of glycogen as a precursor of mannosyl residues in glycoconjugates. J Biol Chem. 2004 Mar 26;279(13):12076-80. Epub 2004 Jan 16.
9. Holloszy JO: Exercise-induced increase in muscle insulin sensitivity. J Appl Physiol (1985). 2005 Jul;99(1):338-43.
10. Fleming I, Schulz C, Fichtlscherer B, Kemp BE, Fisslthaler B, Busse R: AMP-activated protein kinase (AMPK) regulates the insulin-induced activation of the nitric oxide synthase in human platelets. Thromb Haemost. 2003 Nov;90(5):863-71.
11. Koistinen HA, Galuska D, Chibalin AV, Yang J, Zierath JR, Holman GD, Wallberg-Henriksson H: 5-amino-imidazole carboxamide riboside increases glucose transport and cell-surface GLUT4 content in skeletal muscle from subjects with type 2 diabetes. Diabetes. 2003 May;52(5):1066-72.
12. Koistinen HA, Chibalin AV, Zierath JR: Aberrant p38 mitogen-activated protein kinase signalling in skeletal muscle from Type 2 diabetic patients. Diabetologia. 2003 Oct;46(10):1324-8. Epub 2003 Aug 23.
13. Morris GS, Simmonds HA, Davies PM: Use of biological fluids for the rapid diagnosis of potentially lethal inherited disorders of human purine and pyrimidine metabolism. Biomed Chromatogr. 1986 Jun;1(3):109-18.
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=12997251
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=24402866