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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:40 UTC
Update Date2020-04-23 20:54:05 UTC
HMDB IDHMDB0003192
Secondary Accession Numbers
  • HMDB03192
Metabolite Identification
Common Name5-Aminoimidazole-4-carboxamide
Description5-Aminoimidazole-4-carboxamide, also known as AIC or 4-amino-5-carbamoylimidazole, belongs to the class of organic compounds known as aminoimidazoles. These are organic compounds containing an amino group linked to an imidazole ring. 5-Aminoimidazole-4-carboxamide is a very strong basic compound (based on its pKa). 5-Aminoimidazole-4-carboxamide exists in all living organisms, ranging from bacteria to humans. 5-aminoimidazole-4-carboxamide and phosphoribosyl pyrophosphate can be biosynthesized from AICAR through the action of the enzyme adenine phosphoribosyltransferase. In humans, 5-aminoimidazole-4-carboxamide is involved in purine metabolism. An aminoimidazole in which the amino group is at C-5 with a carboxamido group at C-4. 5-Aminoimidazole-4-carboxamide is a potentially toxic compound.
Structure
Data?1582752265
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 Weight126.1166
Monoisotopic Molecular Weight126.054160834
IUPAC Name4-amino-1H-imidazole-5-carboxamide
Traditional Name4-aminoimidazole-5-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
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
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.10HANSCH,C ET AL. (1995)
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility124 g/LALOGPS
logP10(-1.2) g/LALOGPS
logP10(-0.96) g/LChemAxon
logS10(-0.01) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+124.75931661259
DarkChem[M-H]-120.84931661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 5-Aminoimidazole-4-carboxamide GC-MS (3 TMS)splash10-0f9i-4965000000-81d31245e06d3f90edaf2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Aminoimidazole-4-carboxamide GC-MS (4 TMS)splash10-0kgk-3936100000-5d3d51d18ff3e42df0e82014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Aminoimidazole-4-carboxamide GC-MS (Non-derivatized)splash10-0f9i-4965000000-81d31245e06d3f90edaf2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Aminoimidazole-4-carboxamide GC-MS (Non-derivatized)splash10-0kgk-3936100000-5d3d51d18ff3e42df0e82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Aminoimidazole-4-carboxamide GC-EI-TOF (Non-derivatized)splash10-000i-3690000000-139a77fec9d1fff114cd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Aminoimidazole-4-carboxamide GC-EI-TOF (Non-derivatized)splash10-0f9i-1943000000-fc9ed76a2b879a05cac32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Aminoimidazole-4-carboxamide GC-EI-TOF (Non-derivatized)splash10-0f6t-0924100000-3f9bf805d01a76aee6722017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Aminoimidazole-4-carboxamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0059-9700000000-59d0b74e7172f25684a92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Aminoimidazole-4-carboxamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide LC-ESI-QQ , negative-QTOFsplash10-004i-0900000000-7f5a5c4e183bae4dac942017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide LC-ESI-QQ , negative-QTOFsplash10-0a6r-4900000000-f098009008beac308c092017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide LC-ESI-QQ , negative-QTOFsplash10-0a4l-9100000000-0558a1cf6f49c407a5c92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-49775423db52b263ab352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-61b854e636df8aefa7432017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide LC-ESI-QQ , positive-QTOFsplash10-03fr-0900000000-dbf2f2a8c104b1886d612017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide LC-ESI-QQ , positive-QTOFsplash10-03di-0900000000-4e7fa2397876cb8faa222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide LC-ESI-QQ , positive-QTOFsplash10-03di-4900000000-c5cc732d595521342e282017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide LC-ESI-QQ , positive-QTOFsplash10-0a4i-9200000000-4f8ffe0195fc8b4eefb32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide LC-ESI-QQ , positive-QTOFsplash10-0a4i-9000000000-2475e395f0201d1ae8dc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide 35V, Negative-QTOFsplash10-0006-9000000000-e01c782c531e25d733322021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide 10V, Positive-QTOFsplash10-004i-0900000000-5ac6303648d30c83dd8c2015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide 20V, Positive-QTOFsplash10-03e9-5900000000-891e8af2ee696c82bb672015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide 40V, Positive-QTOFsplash10-0a4i-9100000000-d969e00c4e0a26137fb42015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide 10V, Negative-QTOFsplash10-004i-5900000000-38872de2bfb260a5d96f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide 20V, Negative-QTOFsplash10-0563-9400000000-5d37f6e245dbc41ac3e42015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide 40V, Negative-QTOFsplash10-00kf-9000000000-9797d793034ec5f4f97f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide 10V, Positive-QTOFsplash10-004i-0900000000-00d6654a49bf268f862d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide 20V, Positive-QTOFsplash10-01q9-9300000000-8eb581fb8e27a0073dde2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide 40V, Positive-QTOFsplash10-00kf-9000000000-a1482203ba6eb659c7552021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide 10V, Negative-QTOFsplash10-004l-8900000000-fa9ba502d467ade9fdca2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide 20V, Negative-QTOFsplash10-0006-9000000000-26ef6e91d6b3541e37482021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Aminoimidazole-4-carboxamide 40V, Negative-QTOFsplash10-0006-9000000000-74703663982d7ee978ef2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Fibroblasts
  • Platelet
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
UrineDetected and Quantified<0.11 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Phenol Explorer Compound IDNot Available
FooDB IDFDB023121
KNApSAcK IDNot Available
Chemspider ID9298
KEGG Compound IDC04051
BioCyc IDCPD-3762
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID629
PubChem Compound9679
PDB IDNot Available
ChEBI ID2030
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 (1985). 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 (1985). 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