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Human Metabolome Database Version 3.5

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Showing metabocard for 5-Aminoimidazole (HMDB03929)

Record Information
Version 3.5
Creation Date 2006-08-13 01:23:28 -0600
Update Date 2013-02-08 17:12:49 -0700
HMDB ID HMDB03929
Secondary Accession Numbers None
Metabolite Identification
Common Name 5-Aminoimidazole
Description Because 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 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 4-Aminoimidazole
  2. Aminoimidazole
Chemical Formula C3H5N3
Average Molecular Weight 83.0919
Monoisotopic Molecular Weight 83.048347175
IUPAC Name 1H-imidazol-5-amine
Traditional IUPAC Name 3H-imidazol-4-amine
CAS Registry Number 4919-03-3
SMILES NC1=CN=CN1
InChI Identifier InChI=1S/C3H5N3/c4-3-1-5-2-6-3/h1-2H,4H2,(H,5,6)
InChI Key QRZMXADUXZADTF-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteromonocyclic Compounds
Class Azoles
Sub Class Imidazoles
Other Descriptors
  • Imidazoles
  • a small molecule(Cyc)
  • aminoimidazole(ChEBI)
Substituents
  • N/A
Direct Parent Aminoimidazoles
Ontology
Status Expected and Not 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 Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 319 g/L ALOGPS
LogP -1.08 ALOGPS
LogP -0.88 ChemAxon
LogS 0.58 ALOGPS
pKa (strongest acidic) 13.84 ChemAxon
pKa (strongest basic) 8.36 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 54.7 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 22.97 ChemAxon
Polarizability 7.97 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023250
KNApSAcK ID Not Available
Chemspider ID 470 Link_out
KEGG Compound ID C05239 Link_out
BioCyc ID PHOSPHORIBOSYL-CARBOXY-AMINOIMIDAZOLE Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB03929 Link_out
Metagene Link HMDB03929 Link_out
METLIN ID 6989 Link_out
PubChem Compound 484 Link_out
PDB ID Not Available
ChEBI ID 16607 Link_out
References
Synthesis Reference Not 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 Link_out