CHEBI:2030 - 5-aminoimidazole-4-carboxamide

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ChEBI Name 5-aminoimidazole-4-carboxamide ChEBI ID CHEBI:2030 Definition An aminoimidazole in which the amino group is at C-5 with a carboxamido group at C-4. Stars This entity has been manually annotated by the ChEBI Team. Secondary ChEBI IDs CHEBI:20544 Supplier Information ChemicalBook:CB2438232, ChemicalBook:CB9438231, eMolecules:984096, eMolecules:520361, ZINC000003861263 Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Formula C4H6N4O Net Charge 0 Average Mass 126.11660 Monoisotopic Mass 126.05416 InChI InChI=1S/C4H6N4O/c5-3-2(4(6)9)7-1-8-3/h1H,5H2,(H2,6,9)(H,7,8) InChIKey DVNYTAVYBRSTGK-UHFFFAOYSA-N SMILES NC(=O)c1nc[nH]c1N Metabolite of Species Details Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed Roles Classification Biological Role(s): mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). View more via ChEBI Ontology ChEBI Ontology Outgoing 5-aminoimidazole-4-carboxamide (CHEBI:2030) has role mouse metabolite (CHEBI:75771) 5-aminoimidazole-4-carboxamide (CHEBI:2030) is a aminoimidazole (CHEBI:22512) 5-aminoimidazole-4-carboxamide (CHEBI:2030) is a monocarboxylic acid amide (CHEBI:29347) IUPAC Name 5-amino-1H-imidazole-4-carboxamide Synonyms Sources 4-amino-5-carbamoylimidazole MetaCyc 4-amino-5-imidazolecarboxamide MetaCyc 5(4)-amino-4(5)-imidazolecarboxamide MetaCyc 5-amino-4-imidazolecarboxyamide UniProt 5-amino-4-imidazolecarboxyamide MetaCyc 5-Amino-4-imidazolecarboxyamide KEGG COMPOUND 5-aminoimidazole-4-carboxamide MetaCyc Manual Xrefs Databases 1994 DrugCentral 5AC PDBeChem C04051 KEGG COMPOUND CPD-3762 MetaCyc HMDB0003192 HMDB View more database links Registry Number Type Source 3938 Reaxys Registry Number Reaxys Citations Choi JH, Ohnishi T, Yamakawa Y, Takeda S, Sekiguchi S, Maruyama W, Yamashita K, Suzuki T, Morita A, Ikka T, Motohashi R, Kiriiwa Y, Tobina H, Asai T, Tokuyama S, Hirai H, Yasuda N, Noguchi K, Asakawa T, Sugiyama S, Kan T, Kawagishi H (2014) The source of "fairy rings": 2-azahypoxanthine and its metabolite found in a novel purine metabolic pathway in plants. Angewandte Chemie (International ed. in English) 53, 1552-1555 [PubMed:24402866] [show Abstract] Rings or arcs of fungus-stimulated plant growth occur worldwide; these are commonly referred to as "fairy rings". In 2010, we discovered 2-azahypoxanthine (AHX), a compound responsible for the fairy-ring phenomenon caused by fungus; AHX stimulated the growth of all the plants tested. Herein, we reveal the isolation and structure determination of a common metabolite of AHX in plants, 2-aza-8-oxohypoxanthine (AOH). AHX is chemically synthesized from 5-aminoimidazole-4-carboxamide (AICA), and AHX can be converted into AOH by xanthine oxidase. AICA is one of the members of the purine metabolic pathway in animals, plants, and microorganisms. However, further metabolism of AICA remains elusive. Based on these results and facts, we hypothesized that plants themselves produce AHX and AOH through a pathway similar to the chemical synthesis. Herein, we demonstrate the existence of endogenous AHX and AOH and a novel purine pathway to produce them in plants. STEWART RC, SEVAG MG (1952) 4-Amino-5-imidazolecarboxamide; role of carbohydrates as critical factors for its accumulation. Archives of biochemistry and biophysics 41, 91-93 [PubMed:12997251] Last Modified 22 February 2017