3031-95-6
Chemical Structure
SAICAR
- CAS No.: 3031-95-6
- Formula:C13H19N4O12P
- Molecular Weight:454.28
IUPAC Name: (5-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-((phosphonooxy)methyl)tetrahydrofuran-2-yl)-1H-imidazole-4-carbonyl)-L-aspartic acid
InChIKey: NAQGHJTUZRHGAC-ZZZDFHIKSA-N
SMILES: O=C(O)C[C@@H](C(O)=O)NC(C1=C(N)N([C@H]2[C@@H]([C@@H]([C@@H](COP(O)(O)=O)O2)O)O)C=N1)=O
Biological Activity: SAICAR is an intermediate of de novo purine nucleotide biosynthesis, activates pyruvate kinase isoform M2 (PKM2) in an isozyme-selective manner, with an EC50 of 0.3 mM. SAICAR stimulates PKM2 and promotes cancer cell survival in glucose-limited conditions[1][2].
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SAICAR | 99.57% | SAICAR is an intermediate of de novo purine nucleotide biosynthesis, activates pyruvate kinase isoform M2 (PKM2) in an isozyme-selective manner, with an EC50 of 0.3 mM. SAICAR stimulates PKM2 and promotes cancer cell survival in glucose-limited conditions. | ||||||||||||||||||||
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SAICAR-d3 | SAICAR-d3 is the deuterium labeled SAICAR. SAICAR is an intermediate of de novo purine nucleotide biosynthesis, activates pyruvate kinase isoform M2 (PKM2) in an isozyme-selective manner, with an EC50 of 0.3 mM. SAICAR stimulates PKM2 and promotes cancer cell survival in glucose-limited conditions. | |||||||||||||||||||||
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Similarity Score 0.84
HY-154945N-(5-Amino-1-ribosyl-4-imidazolecarbonyl)-L-aspartic acid -
Similarity Score 0.72
HY-134356AICA-riboside, 5′-phosphate -
Similarity Score 0.71
HY-133154Carboxyaminoimidazole ribotide -
Similarity Score 0.66
HY-133157FAICAR -
Similarity Score 0.64
HY-13417ARAICAR phosphate (Standard) -
Similarity Score 0.63
HY-W743767Mizoribine 5'-monophosphate -
Similarity Score 0.62
HY-127137Adenylosuccinic acid -
Similarity Score 0.59
HY-13417RAICAR (Standard) -
Similarity Score 0.59
HY-13417SAICAR-13C2,15N -
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References
- [1]. Keller KE, et al. SAICAR stimulates pyruvate kinase isoform M2 and promotes cancer cell survival in glucose-limited conditions. Science. 2012 Nov 23;338(6110):1069-72. [Content Brief]
- [2]. Keller KE, et al. SAICAR induces protein kinase activity of PKM2 that is necessary for sustained proliferative signaling of cancer cells. Mol Cell. 2014 Mar 6;53(5):700-9. [Content Brief]
