Common Name(2s)-2-[5-amino-1-(5-phospho-beta-d-ribosyl)imidazole-4-carboxamido]succinate
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
Molecular FormulaC13H19N4O12P
Average Mass454.28330
Monoisotopic Mass454.07371
IUPAC Name(2S)-2-({5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazol-4-yl}formamido)butanedioic acid
Traditional Name(2s)-2-({5-amino-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazol-4-yl}formamido)butanedioic acid
CAS Registry Number3031-95-6
SMILESNc1c(C(=O)N[C@@H](CC(=O)[O-])C(=O)[O-])ncn1[C@@H]1O[C@H](COP(=O)([O-])[O-])[C@@H](O)[C@H]1O
InChI IdentifierInChI=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
CHEBI IDCHEBI:58443
HMDB IDHMDB0000797
MiMeDB IDMMDBc0033033
Pathways
NameSMPDB/PathBank
Purine metabolism
Adenosine Deaminase Deficiency
Adenylosuccinate Lyase Deficiency
AICA-Ribosiduria
Molybdenum Cofactor Deficiency
Purine Nucleoside Phosphorylase Deficiency
Xanthine Dehydrogenase Deficiency (Xanthinuria)
Lesch-Nyhan Syndrome (LNS)
Gout or Kelley-Seegmiller Syndrome
Azathioprine Action Pathway
Mercaptopurine Action Pathway
Thioguanine Action Pathway
Xanthinuria type I
Xanthinuria type II
Adenine phosphoribosyltransferase deficiency (APRT)
Mitochondrial DNA depletion syndrome
Myoadenylate deaminase deficiency
StateSolid
Water Solubility1.73e+00 g/l
logP-1.82
logS-2.42
pKa (Strongest Acidic)1.22
pKa (Strongest Basic)4.54
Hydrogen Acceptor Count13
Hydrogen Donor Count8
Polar Surface Area263.99 Ų
Rotatable Bond Count9
Physiological Charge-4
Formal Charge0
Refractivity90.65 m³·mol⁻¹
Polarizability38.50

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