10018-94-7 , S-(2E)-2-Octenoate coenzyme A
C29H48N7O17P3S / 891.72
(2E)-Octenoyl-CoA, also known as (E)-S-2-octenoate, belongs to the class of organic compounds known as medium-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a medium-chain 2-enoyl chain of 5 to 12 carbon atoms (2E)-Octenoyl-CoA is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa) (2E)-Octenoyl-CoA has been primarily detected in urine. Within the cell, (2E)-octenoyl-CoA is primarily located in the cytoplasm (2E)-Octenoyl-CoA exists in all eukaryotes, ranging from yeast to humans. In humans, (2E)-octenoyl-CoA is involved in the fatty acid metabolism pathway (2E)-Octenoyl-CoA is also involved in several metabolic disorders, some of which include the mitochondrial Beta-oxidation OF short chain saturated fatty acids pathway, the mitochondrial Beta-oxidation OF medium chain saturated fatty acids pathway, very-long-chain acyl CoA dehydrogenase deficiency (vlcad), and long chain acyl-CoA dehydrogenase deficiency (lcad).
S-2-Octenoate CoA is a natural ligand for the orphan G protein-coupled receptor GPR120. This ligand has been shown to activate AMPK and PPARα, leading to increased fatty acid oxidation and decreased lipid synthesis. Studies have shown that S-2-octenoate coenzyme A inhibits the production of inflammatory cytokines, such as IL-6, IL-1β, TNFα and IFNγ. It also inhibits the migration of leukocytes and platelets. The high purity of this ligand ensures minimal background interference in immunoassays.
CAS Number | 10018-94-7 |
Product Name | S-[2-[3-[[4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] (E)-oct-2-enethioate |
IUPAC Name | S-[2-[3-[[4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] oct-2-enethioate |
Molecular Formula | C29H48N7O17P3S |
Molecular Weight | 891.7 g/mol |
InChI | InChI=1S/C29H48N7O17P3S/c1-4-5-6-7-8-9-20(38)57-13-12-31-19(37)10-11-32-27(41)24(40)29(2,3)15-50-56(47,48)53-55(45,46)49-14-18-23(52-54(42,43)44)22(39)28(51-18)36-17-35-21-25(30)33-16-34-26(21)36/h8-9,16-18,22-24,28,39-40H,4-7,10-15H2,1-3H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/t18-,22-,23-,24?,28-/m1/s1 |
InChI Key | CPSDNAXXKWVYIY-FFJUWABQSA-N |
SMILES | CCCCCC=CC(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)O |
Canonical SMILES | CCCCCC=CC(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)O |
Isomeric SMILES | CCCCC/C=C/C(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)O |
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