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Merck
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重要文件

SMB01385

Sigma-Aldrich

SAICAR

≥95% (HPLC)

同義詞:

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

經驗公式(希爾表示法):
C13H19N4O12P
CAS號碼:
分子量::
454.28
分類程式碼代碼:
12352202
NACRES:
NA.21
暫時無法取得訂價和供貨情況

生物源

synthetic

品質等級

化驗

≥95% (HPLC)

形狀

solid

應用

metabolomics

運輸包裝

2-8°C

儲存溫度

2-8°C

SMILES 字串

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 密鑰

NAQGHJTUZRHGAC-ZZZDFHIKSA-N

一般說明

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.

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable


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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
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)
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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