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:CB0456205, eMolecules:29542138, ZINC000003869280
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Phosphoserine (abbreviated as SEP or J) is an ester of serine and phosphoric acid. Phosphoserine is a component of many proteins as the result of posttranslational modifications. The phosphorylation of the alcohol functional group in serine to produce phosphoserine is catalyzed by various types of kinases. Through the use of technologies that utilize an expanded genetic code, phosphoserine can also be incorporated into proteins during translation. It is a normal metabolite found in human biofluids. Phosphoserine has three potential coordination sites (carboxyl, amine and phosphate group) Determination of the mode of coordination between phosphorylated ligands and metal ions occurring in an organism is a first step to explain the function of the phosphoserine in bioinorganic processes.
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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