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Human Metabolome Database Version 3.5

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Showing metabocard for 5-Aminoimidazole-4-carboxamide (HMDB03192)

Record Information
Version 3.5
Creation Date 2006-05-22 09:12:40 -0600
Update Date 2013-02-08 17:12:20 -0700
HMDB ID HMDB03192
Secondary Accession Numbers None
Metabolite Identification
Common Name 5-Aminoimidazole-4-carboxamide
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. -- Pubchem.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C4H6N4O
Average Molecular Weight 126.1166
Monoisotopic Molecular Weight 126.054160834
IUPAC Name 4-amino-1H-imidazole-5-carboxamide
Traditional IUPAC Name 5-amino-3H-imidazole-4-carboxamide
CAS Registry Number 360-97-4
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 Key DVNYTAVYBRSTGK-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteromonocyclic Compounds
Class Azoles
Sub Class Imidazoles
Other Descriptors
  • Imidazoles
  • aminoimidazole(ChEBI)
  • monocarboxylic acid amide(ChEBI)
Substituents
  • Aminoimidazole
  • Carboxamide Group
  • Primary Carboxylic Acid Amide
Direct Parent Imidazole Carboxamides
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -1.10 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 124 g/L ALOGPS
LogP -1.16 ALOGPS
LogP -0.96 ChemAxon
LogS -0.01 ALOGPS
pKa (strongest acidic) 12.74 ChemAxon
pKa (strongest basic) 5.26 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 97.79 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 32.98 ChemAxon
Polarizability 11.37 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Fibroblasts
  • Platelet
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
0.21 (0.05-0.52) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.47 (0.20-0.82) umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
5.55 (0.79 - 39.67) uM Adult (>18 years old) Both Malignant melanoma or sarcoma After receiving 2.65-6.85 mg dacarbazine/kg...
Associated Disorders and Diseases
Disease References
Melanoma
  • 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 Link_out
    Sarcoma
    • 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 Link_out
      Associated OMIM IDs
      DrugBank ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB023121
      KNApSAcK ID Not Available
      Chemspider ID 9298 Link_out
      KEGG Compound ID C04051 Link_out
      BioCyc ID CPD-3762 Link_out
      BiGG ID Not Available
      Wikipedia Link AIC Link_out
      NuGOwiki Link HMDB03192 Link_out
      Metagene Link HMDB03192 Link_out
      METLIN ID 629 Link_out
      PubChem Compound 9679 Link_out
      PDB ID 5AC Link_out
      ChEBI ID 2030 Link_out
      References
      Synthesis Reference Not Available
      Material Safety Data Sheet (MSDS) Download (PDF)
      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. 2001 Sep;91(3):1073-83. Pubmed: 11509501 Link_out
      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. Pubmed: 15149951 Link_out
      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. Pubmed: 16483872 Link_out
      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. Pubmed: 4026274 Link_out
      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. Pubmed: 11598104 Link_out
      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. Pubmed: 17015 Link_out
      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. Pubmed: 12730239 Link_out
      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. Pubmed: 14729664 Link_out
      9. Holloszy JO: Exercise-induced increase in muscle insulin sensitivity. J Appl Physiol. 2005 Jul;99(1):338-43. Pubmed: 16036907 Link_out
      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. Pubmed: 14597982 Link_out
      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. Pubmed: 12716734 Link_out
      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. Pubmed: 12937895 Link_out
      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. Pubmed: 3506820 Link_out
      Enzymes
      Name: Adenine phosphoribosyltransferase
      Reactions:
      • AMP + diphosphate = adenine + 5-phospho-alpha-D-ribose 1-diphosphate [RN:R00190]
      Gene Name: APRT
      Uniprot ID: P07741 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Adenylosuccinate lyase
      Reactions:
      • (1) N6-(1,2-dicarboxyethyl)AMP = fumarate + AMP [RN:R01083]
      • (2) (S)-2-[5-amino-1-(5-phospho-D-ribosyl)imidazole-4- carboxamido]succinate = fumarate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide [RN:R04559]
      Gene Name: ADSL
      Uniprot ID: P30566 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Bifunctional purine biosynthesis protein PURH
      Reactions:
      • IMP + H2O = 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide [RN:R01127]
      Gene Name: ATIC
      Uniprot ID: P31939 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA