You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-05-22 15:12:40 UTC
Update Date2013-02-09 00:12:20 UTC
HMDB IDHMDB03192
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Aminoimidazole-4-carboxamide
Description5-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. -- Pubchem.
Structure
Thumb
Synonyms
  1. 4-Amino-5-Imidazolecarboxamide
  2. 4-Aminoimidazole-5-carboxamide
  3. 4-Carbamoyl-5-aminoimidazole
  4. 4-Carboxamido-5-aminoimidazole
  5. 5-Amino-1H-Imidazole-4-carboxamide
  6. 5-Amino-4-imidazolecarboxamide
  7. 5-Amino-Imidazole-4-carboxamide
  8. 5-Aminoimidazol-4-carboxamide
  9. 5-Aminoimidazole-4-carboxamide ribotide
  10. AIC
  11. AICA
  12. AICAR
  13. Colahepat
Chemical FormulaC4H6N4O
Average Molecular Weight126.1166
Monoisotopic Molecular Weight126.054160834
IUPAC Name4-amino-1H-imidazole-5-carboxamide
Traditional Name5-amino-3H-imidazole-4-carboxamide
CAS Registry Number360-97-4
SMILES
NC(=O)C1=C(N)N=CN1
InChI Identifier
InChI=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
KingdomOrganic Compounds
Super ClassAromatic Heteromonocyclic Compounds
ClassAzoles
Sub ClassImidazoles
Other Descriptors
  • Imidazoles
  • aminoimidazole(ChEBI)
  • monocarboxylic acid amide(ChEBI)
Substituents
  • Aminoimidazole
  • Carboxamide Group
  • Primary Carboxylic Acid Amide
Direct ParentImidazole Carboxamides
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.10HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility124.0ALOGPS
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
Spectra
SpectraGC-MS
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Fibroblasts
  • Muscle
  • Platelet
  • Skeletal Muscle
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.21 (0.05-0.52) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.47 (0.20-0.82) umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified5.55 (0.79 - 39.67) uMAdult (>18 years old)Both
Malignant melanoma or sarcoma
details
Associated Disorders and Diseases
Disease References
Melanoma
  1. Breithaupt H, Dammann A, Aigner K: Pharmacokinetics of dacarbazine (DTIC) and its metabolite 5-aminoimidazole-4-carboxamide (AIC) following different dose schedules. Cancer Chemother Pharmacol. 1982;9(2):103-9. Pubmed: 7172404
Sarcoma
  1. Breithaupt H, Dammann A, Aigner K: Pharmacokinetics of dacarbazine (DTIC) and its metabolite 5-aminoimidazole-4-carboxamide (AIC) following different dose schedules. Cancer Chemother Pharmacol. 1982;9(2):103-9. Pubmed: 7172404
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023121
KNApSAcK IDNot Available
Chemspider ID9298
KEGG Compound IDC04051
BioCyc IDCPD-3762
BiGG IDNot Available
Wikipedia LinkAIC
NuGOwiki LinkHMDB03192
Metagene LinkHMDB03192
METLIN ID629
PubChem Compound9679
PDB ID5AC
ChEBI ID2030
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. Pubmed: 11598104
  2. 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. Pubmed: 12716734
  3. 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. Pubmed: 12937895
  4. 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. Pubmed: 3506820
  5. 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. 2001 Sep;91(3):1073-83. Pubmed: 11509501
  6. 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. Pubmed: 15149951
  7. 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. Pubmed: 16483872
  8. 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. Pubmed: 4026274
  9. 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. Pubmed: 17015
  10. 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. Pubmed: 12730239
  11. 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. Pubmed: 14729664
  12. Holloszy JO: Exercise-induced increase in muscle insulin sensitivity. J Appl Physiol. 2005 Jul;99(1):338-43. Pubmed: 16036907
  13. 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. Pubmed: 14597982

Enzymes

General function:
Involved in adenine phosphoribosyltransferase activity
Specific function:
Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis.
Gene Name:
APRT
Uniprot ID:
P07741
Molecular weight:
19607.535
Reactions
AICAR + Pyrophosphate → 5-Aminoimidazole-4-carboxamide + Phosphoribosyl pyrophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ADSL
Uniprot ID:
P30566
Molecular weight:
54888.735
General function:
Involved in IMP cyclohydrolase activity
Specific function:
Bifunctional enzyme that catalyzes 2 steps in purine biosynthesis.
Gene Name:
ATIC
Uniprot ID:
P31939
Molecular weight:
64615.255