SMB01385
SAICAR
≥95% (HPLC)
Synonym(s):
N-[[5-amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazol-4-yl]carbonyl]-L-aspartic acid, Succino-AICAR, Succinyl-AICAR
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About This Item
Empirical Formula (Hill Notation):
C13H19N4O12P
CAS Number:
Molecular Weight:
454.28
UNSPSC Code:
12352202
NACRES:
NA.21
biological source
synthetic
Quality Level
assay
≥95% (HPLC)
form
solid
application(s)
metabolomics
shipped in
2-8°C
storage temp.
2-8°C
SMILES string
NC1=C(N=CN1[C@H]2[C@H](O)[C@H](O)[C@@H](COP(O)(O)=O)O2)C(N[C@@H](CC(O)=O)C(O)=O)=O
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
InChI key
NAQGHJTUZRHGAC-ZZZDFHIKSA-N
General description
SAICAR is an intermediate in purine metabolism. SAICAR is converted from 5-amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate (CAIR, Carboxy-AIR, carboxyaminoimidazole ribotide; CAS 6001-14-5) by phosphoribosylaminoimidazole-succinocarboxamide synthase (SAICAR synthase). SAICAR (a ribotide) can lose its phosphate group leading to the appearance of a riboside known as succinylaminoimidazolecarboxamide riboside (SAICAriboside or SAICAr) in cerebrospinal fluid, in urine, and, to a lesser extent, in plasma. When present in sufficiently high levels, SAICAR can act as an oncometabolite, where it promotes tumour growth & survival under glucose-limited conditions by stimulating pyruvate kinase isoform M2 (PKM2) and promoting aerobic glycolysis.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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A mild form of adenylosuccinate lyase deficiency in absence of typical brain MRI features diagnosed by whole exome sequencing
Macchiaiolo Marina, et al.
Italian Journal of Pediatrics, 43, 65-65 (2017)
Extended diagnosis of purine and pyrimidine disorders from urine: LC MS/MS assay development and clinical validation
Monostori Peter, et al.
PLoS ONE, 14, e0212458-e0212458 (2019)
Kirstie E Keller et al.
Molecular cell, 53(5), 700-709 (2014-03-13)
Abnormal metabolism and sustained proliferation are hallmarks of cancer. Pyruvate kinase M2 (PKM2) is a metabolic enzyme that plays important roles in both processes. Recently, PKM2 was shown to have protein kinase activity phosphorylating histone H3 and promoting cancer cell
Global Trade Item Number
| SKU | GTIN |
|---|---|
| SMB01385-1MG | 04065270018588 |