phorbol 12-myristate 13-acetate   

GtoPdb Ligand ID: 2341

Abbreviated name: PMA
Synonyms: 12-O-tetradecanoylphorbol-13-acetate | tetradecanoyl-β-phorbol acetate | TPA
Compound class: Synthetic organic
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 17
Topological polar surface area 130.36
Molecular weight 616.4
XLogP 6.51
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES CCCCCCCCCCCCCC(=O)OC1C(C)C2(O)C(C3C1(OC(=O)C)C3(C)C)C=C(CC1(C2C=C(C1=O)C)O)CO
Isomeric SMILES CCCCCCCCCCCCCC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@H]([C@H]3[C@]1(OC(=O)C)C3(C)C)C=C(C[C@]1([C@H]2C=C(C1=O)C)O)CO
InChI InChI=1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1
InChI Key PHEDXBVPIONUQT-RGYGYFBISA-N
References
1. Mao J, Wang X, Chen F, Wang R, Rojas A, Shi Y, Piao H, Jiang C. (2004)
Molecular basis for the inhibition of G protein-coupled inward rectifier K(+) channels by protein kinase C.
Proc. Natl. Acad. Sci. U.S.A., 101 (4): 1087-92. [PMID:14732702]
2. Santi CM, Ferreira G, Yang B, Gazula VR, Butler A, Wei A, Kaczmarek LK, Salkoff L. (2006)
Opposite regulation of Slick and Slack K+ channels by neuromodulators.
J. Neurosci., 26 (19): 5059-68. [PMID:16687497]
3. Watanabe H, Davis JB, Smart D, Jerman JC, Smith GD, Hayes P, Vriens J, Cairns W, Wissenbach U, Prenen J et al.. (2002)
Activation of TRPV4 channels (hVRL-2/mTRP12) by phorbol derivatives.
J. Biol. Chem., 277 (16): 13569-77. [PMID:11827975]
4. Xu F, Satoh E, Iijima T. (2003)
Protein kinase C-mediated Ca2+ entry in HEK 293 cells transiently expressing human TRPV4.
Br. J. Pharmacol., 140 (2): 413-21. [PMID:12970074]