CHEBI:58443 - SAICAR(4−)

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name SAICAR(4−)
ChEBI ID CHEBI:58443
ChEBI ASCII Name SAICAR(4-)
Definition An organophosphate oxoanion that is the tetraanionic form of SAICAR. It is the major species at pH 7.3.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information No supplier information found for this compound.
Download Molfile XML SDF
Formula C13H15N4O12P
Net Charge -4
Average Mass 450.25380
Monoisotopic Mass 450.04460
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)/p-4/t4-,5+,8+,9+,12+/m0/s1
InChIKey NAQGHJTUZRHGAC-ZZZDFHIKSA-J
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
Saccharomyces cerevisiae (NCBI:txid4932) Source: yeast.sf.net See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing SAICAR(4−) (CHEBI:58443) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
SAICAR(4−) (CHEBI:58443) has role human metabolite (CHEBI:77746)
SAICAR(4−) (CHEBI:58443) is a dicarboxylic acid dianion (CHEBI:28965)
SAICAR(4−) (CHEBI:58443) is a organophosphate oxoanion (CHEBI:58945)
SAICAR(4−) (CHEBI:58443) is conjugate base of SAICAR (CHEBI:18319)
Incoming SAICAR (CHEBI:18319) is conjugate acid of SAICAR(4−) (CHEBI:58443)
IUPAC Names
(2S)-2-[5-amino-1-(5-O-phosphonato-β-D-ribosyl)imidazole-4-carboxamido]succinate
5-amino-N-[(1S)-1,2-dicarboxylatoethyl]-1-(5-O-phosphonato-β-D-ribofuranosyl)-1H-imidazole-4-carboxamide
Synonym Source
(2S)-2-[5-amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamido]succinate UniProt
Manual Xref Database
P-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE MetaCyc
View more database links
Citations
Keller KE, Doctor ZM, Dwyer ZW, Lee YS (2014)
SAICAR induces protein kinase activity of PKM2 that is necessary for sustained proliferative signaling of cancer cells.
Molecular cell 53, 700-709 [PubMed:24606918]
[show Abstract]
Keller KE, Tan IS, Lee YS (2012)
SAICAR stimulates pyruvate kinase isoform M2 and promotes cancer cell survival in glucose-limited conditions.
Science (New York, N.Y.) 338, 1069-1072 [PubMed:23086999]
[show Abstract]
Last Modified
21 January 2016