CHEBI:18319 - SAICAR

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ChEBI Name SAICAR
ChEBI ID CHEBI:18319
Definition A 1-(phosphoribosyl)imidazolecarboxamide resulting from the formal condesation of the darboxy group of 5-amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid with the amino group of L-aspartic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Margaret Duesbury
Secondary ChEBI IDs CHEBI:11028, CHEBI:572, CHEBI:18965, CHEBI:78110
Supplier Information ChemicalBook:CB9375521, ChemicalBook:CB7162318, eMolecules:496860, ZINC000001081581
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Deoxyadenosine (symbol dA or dAdo) is a deoxyribonucleoside. It is a derivative of the nucleoside adenosine, differing from the latter by the replacement of a hydroxyl group (-OH) by hydrogen (-H) at the 2′ position of its ribose sugar moiety. Deoxyadenosine is the DNA nucleoside A, which pairs with deoxythymidine (T) in double-stranded DNA. In absence of adenosine deaminase (ADA) it accumulates in T lymphocytes and kills these cells resulting in a genetic disorder known as adenosine deaminase severe combined immunodeficiency disease (ADA-SCID).
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Formula C13H19N4O12P
Net Charge 0
Average Mass 454.28330
Monoisotopic Mass 454.07371
InChI InChI=1S/C13H19N4O12P/c14-10-7(11(22)16-4(13(23)24)1-6(18)19)15-3-17(10)12-9(21)8(20)5(29-12)2-28-30(25,26)27/h3-5,8-9,12,20-21H,1-2,14H2,(H,16,22)(H,18,19)(H,23,24)(H2,25,26,27)/t4-,5+,8+,9+,12+/m0/s1
InChIKey NAQGHJTUZRHGAC-ZZZDFHIKSA-N
SMILES Nc1c(ncn1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C(=O)N[C@@H](CC(O)=O)C(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
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ChEBI Ontology
Outgoing SAICAR (CHEBI:18319) has functional parent succinic acid (CHEBI:15741)
SAICAR (CHEBI:18319) has role Escherichia coli metabolite (CHEBI:76971)
SAICAR (CHEBI:18319) has role mouse metabolite (CHEBI:75771)
SAICAR (CHEBI:18319) is a 1-(phosphoribosyl)imidazolecarboxamide (CHEBI:37290)
SAICAR (CHEBI:18319) is conjugate acid of SAICAR(4−) (CHEBI:58443)
Incoming SAICAR(4−) (CHEBI:58443) is conjugate base of SAICAR (CHEBI:18319)
IUPAC Names
(2S)-2-[5-amino-1-(5-O-phosphono-β-D-ribosyl)imidazole-4-carboxamido]succinic acid
N-{[5-amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazol-4-yl]carbonyl}-L-aspartic acid
Synonyms Sources
(S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate KEGG COMPOUND
1-(5'-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole KEGG COMPOUND
1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole KEGG COMPOUND
5'-Phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole KEGG COMPOUND
SAICA riboside ChEBI
SAICAR KEGG COMPOUND
Succino-AICAR HMDB
succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphate ChEBI
succinylaminoimidazolecarboxamide ribose-5'-phosphate ChEBI
Manual Xrefs Databases
C04823 KEGG COMPOUND
HMDB0000797 HMDB
P-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE MetaCyc
Phosphoribosylaminoimidazolesuccinocarboxamide Wikipedia
View more database links
Registry Number Type Source
3031-95-6 CAS Registry Number ChemIDplus
Citations Types Sources
23086999 PubMed citation Europe PMC
24606918 PubMed citation SUBMITTER
Last Modified
09 December 2024