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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

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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分析證明 (COA)

Lot/Batch Number

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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
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
Kirstie E Keller et al.
Science (New York, N.Y.), 338(6110), 1069-1072 (2012-10-23)
Pyruvate kinase isoform M2 (PKM2) plays an important role in the growth and metabolic reprogramming of cancer cells in stress conditions. Here, we report that SAICAR (succinylaminoimidazolecarboxamide ribose-5'-phosphate, an intermediate of the de novo purine nucleotide synthesis pathway) specifically stimulates

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