Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:31:54 UTC
Update Date2025-01-15 17:53:48 UTC
Metabolite IDMMDBc0033033
Metabolite Identification
Common Name(2S)-2-[5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinic acid
DescriptionSAICAR, also known as succinylaminoimidazolecarboxamide ribotide or phosphoribosylaminoimidazolesuccinocarboxamide, is a substrate for the multifunctional protein ADE2. SAICAR is an intermediate in purine metabolism. SAICAR is converted from 5-aminoimidazole-4-carboxyribonucleotide (CAIR) via phosphoribosylaminoimidazolesuccinocarboxamide synthetase (EC: 6.3.2.6) or SAICAR synthase. This enzyme catalyzes the eighth step in the biosynthesis of purine nucleotides. SAICAR (a ribotide) can lose its phosphate group leading to the appearance of a riboside known as succinylaminoimidazolecarboxamide riboside (SAICAriboside) in cerebrospinal fluid, in urine, and, to a lesser extent, in plasma. This particular riboside (called SAICAr) is characteristic of a heritable deficiency known as adenylosuccinate lyase deficiency (ADSL). On the other hand, the ribotide (SAICAR) is generally harmless and is an essential intermediate in purine metabolism. When present in sufficiently high levels, SAICAR can act as an oncometabolite. An oncometabolite is a compound that promotes tumour growth and survival. As an oncometabolite, high levels of SAICAR stimulate pyruvate kinase isoform M2 and promote cancer cell survival in glucose-limited conditions such as aerobic glycolysis (PMID: 23086999 ).
Structure
SynonymsNot Available
Molecular FormulaC13H19N4O12P
Average Mass454.2833
Monoisotopic Mass454.0737086
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number3031-95-6
SMILESNot Available
InChI Identifier
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-/m1/s1
InChI KeyNAQGHJTUZRHGAC-LBGUGVGYSA-N