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Merck
CN

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:
3031-95-6
Molecular Weight:
454.28
UNSPSC Code:
12352202
NACRES:
NA.21

Key Documents

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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

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

biological source

synthetic

assay

≥95% (HPLC)

form

solid

application(s)

metabolomics

shipped in

2-8°C

storage temp.

2-8°C

Quality Level

200

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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Certificates of Analysis (COA)

Lot/Batch Number
0000271884
0000245128
0000239872
0000245128
0000271884

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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)
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)
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
Ming Yan et al.
Biochemistry, 55(33), 4731-4736 (2016-08-03)
Human pyruvate kinase isoform M2 (PKM2) is a glycolytic enzyme isoform implicated in cancer. Malignant cancer cells have higher levels of dimeric PKM2, which is regarded as an inactive form of tetrameric pyruvate kinase. This perceived inactivity has fueled controversy
Roxane Marsac et al.
Genetics, 211(4), 1297-1313 (2019-02-01)
Purine homeostasis is ensured through a metabolic network widely conserved from prokaryotes to humans. Purines can either be synthesized de novo, reused, or produced by interconversion of extant metabolites using the so-called recycling pathway. Although thoroughly characterized in microorganisms, such
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