Hmdb loader
Show more...Show more...Show more...
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 07:23:28 UTC
Update Date2023-02-21 17:16:51 UTC
HMDB IDHMDB0003929
Secondary Accession Numbers
  • HMDB03929
Metabolite Identification
Common Name5-Aminoimidazole
DescriptionBecause of its ability to mimic a low energy status of the cell, the cell-permeable nucleoside 5-aminoimidazole-4-carboxamide (AICA) riboside was proposed as an antineoplastic agent switching off major energy-consuming processes associated with the malignant phenotype (lipid production, DNA synthesis, cell proliferation, cell migration, etc.). Key to the antineoplastic action of AICA riboside is its conversion to ZMP, an AMP mimetic that at high concentrations activates the AMP-activated protein kinase (AMPK). (PMID: 16985054 ).
Structure
Thumb
Synonyms
ValueSource
AminoimidazoleKegg
4-AminoimidazoleKegg
5-AminoimidazoleChEBI
Chemical FormulaC3H5N3
Average Molecular Weight83.0919
Monoisotopic Molecular Weight83.048347175
IUPAC Name1H-imidazol-5-amine
Traditional Name5-aminoimidazole
CAS Registry Number4919-03-3
SMILES
NC1=CN=CN1
InChI Identifier
InChI=1S/C3H5N3/c4-3-1-5-2-6-3/h1-2H,4H2,(H,5,6)
InChI KeyQRZMXADUXZADTF-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
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023250
KNApSAcK IDNot Available
Chemspider ID470
KEGG Compound IDC05239
BioCyc IDCPD-54
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6989
PubChem Compound484
PDB IDNot Available
ChEBI ID16607
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Laikind PK, Seegmiller JE, Gruber HE: Detection of 5'-phosphoribosyl-4-(N-succinylcarboxamide)-5-aminoimidazole in urine by use of the Bratton-Marshall reaction: identification of patients deficient in adenylosuccinate lyase activity. Anal Biochem. 1986 Jul;156(1):81-90. [PubMed:3740420 ]
  2. Beckers A, Organe S, Timmermans L, Vanderhoydonc F, Deboel L, Derua R, Waelkens E, Brusselmans K, Verhoeven G, Swinnen JV: Methotrexate enhances the antianabolic and antiproliferative effects of 5-aminoimidazole-4-carboxamide riboside. Mol Cancer Ther. 2006 Sep;5(9):2211-7. [PubMed:16985054 ]