CHEBI:18406 - AICA ribonucleotide

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ChEBI Name AICA ribonucleotide
ChEBI ID CHEBI:18406
Definition A 1-(phosphoribosyl)imidazolecarboxamide that is acadesine in which the hydroxy group at the 5' position has been converted to its monophosphate derivative.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:573, CHEBI:18966, CHEBI:40739, CHEBI:12102
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Formula C9H15N4O8P
Net Charge 0
Average Mass 338.21120
Monoisotopic Mass 338.06275
InChI InChI=1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1
InChIKey NOTGFIUVDGNKRI-UUOKFMHZSA-N
SMILES NC(=O)c1ncn([C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)c1N
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Arabidopsis thaliana (NCBI:txid3702) See: DOI
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Application(s): cardiovascular drug
A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume.
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ChEBI Ontology
Outgoing AICA ribonucleotide (CHEBI:18406) has functional parent acadesine (CHEBI:28498)
AICA ribonucleotide (CHEBI:18406) has role Escherichia coli metabolite (CHEBI:76971)
AICA ribonucleotide (CHEBI:18406) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
AICA ribonucleotide (CHEBI:18406) has role cardiovascular drug (CHEBI:35554)
AICA ribonucleotide (CHEBI:18406) has role human metabolite (CHEBI:77746)
AICA ribonucleotide (CHEBI:18406) has role mouse metabolite (CHEBI:75771)
AICA ribonucleotide (CHEBI:18406) has role plant metabolite (CHEBI:76924)
AICA ribonucleotide (CHEBI:18406) is a 1-(phosphoribosyl)imidazolecarboxamide (CHEBI:37290)
AICA ribonucleotide (CHEBI:18406) is a aminoimidazole (CHEBI:22512)
AICA ribonucleotide (CHEBI:18406) is conjugate acid of 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide(2−) (CHEBI:58475)
Incoming 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide(2−) (CHEBI:58475) is conjugate base of AICA ribonucleotide (CHEBI:18406)
IUPAC Name
5-amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazole-4-carboxamide
Synonyms Sources
1-(5'-phosphoribosyl)-5-amino-4-imidazolecarboxamide ChEBI
1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide KEGG COMPOUND
5'-phospho-ribosyl-5-amino-4-imidazole carboxamide ChEBI
5'-Phospho-ribosyl-5-amino-4-imidazole carboxamide KEGG COMPOUND
5'-phosphoribosyl-5-amino-4-imidazolecarboxamide ChEBI
5'-Phosphoribosyl-5-amino-4-imidazolecarboxamide KEGG COMPOUND
5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide ChEBI
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide KEGG COMPOUND
5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide ChEBI
5-aminoimidazole-4-carboxamide ribotide ChEBI
5-Aminoimidazole-4-carboxamide ribotide KEGG COMPOUND
5-phosphoribosyl-4-carbamoyl-5-aminoimidazole ChEBI
5-Phosphoribosyl-4-carbamoyl-5-aminoimidazole KEGG COMPOUND
acadesine 5'-monophosphate ChEBI
Aica ribonucleotide ChemIDplus
AICA-ribonucleotide ChEBI
AICAR
Note: (2014-05-21) Note that this synonym is case sensitive: AICAr is used to refer to the nucleoside (lacking the 5'-phosphate group) while AICAR refers to the nucleotide (i.e. with the 5'-phosphate group).
 KEGG COMPOUND
Manual Xrefs Databases
AICA_ribonucleotide Wikipedia
AMZ PDBeChem
C00007383 KNApSAcK
C04677 KEGG COMPOUND
DB01700 DrugBank
ECMDB01517 ECMDB
HMDB0001517 HMDB
YMDB01481 YMDB
View more database links
Registry Numbers Types Sources
3031-94-5 CAS Registry Number KEGG COMPOUND
52565 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
23988673 PubMed citation Europe PMC
25078608 PubMed citation Europe PMC
8227467 PubMed citation Europe PMC
Last Modified
27 January 2016