has role tertiary alpha-hydroxy ketone antineoplastic agent phorbol ester phorbol 13-acetate 12-myristate PMID:15721302 PMID:3593207 chebi_ontology PMID:29872754 PMID:31904021 C=1[C@]2([C@]3([C@@]([C@H](OC(=O)CCCCCCCCCCCCC)[C@H]([C@@]2([C@]4([C@@](C(=O)C(=C4)C)(CC1CO)O)[H])O)C)(C3(C)C)OC(=O)C)[H])[H] PMID:33268675 12-tetradecanoylphorbol 13-acetate PMID:2866623 C36H56O8 CHEBI:37537 PMID:26894087 PMID:27676154 phorbol-12-myristate-13-acetate PMID:32140039 phorbol 12-tetradecanoate 13-acetate 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 PMID:29538403 (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-acetoxy-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl tetradecanoate PMID:29385060 PHEDXBVPIONUQT-RGYGYFBISA-N PMID:18541361 PMID:12421969 KEGG:C05151 PMA PMID:30663866 KEGG:C09199 PMID:33254440 616.39752 PMID:25649981 PMID:31256364 PMID:31019367 phorbol 12-myristate 13-acetate MetaCyc:CPD-19636 PMID:30254419 TPA PMID:27315825 PMID:26826276 Chemspider:25977 PMID:29291631 PMID:22696070 PMID:31194000 PMID:29933732 616.826 PMID:31437790 0 PMID:15822940 PMID:30075941 LIPID_MAPS_instance:LMPR0104330002 12-O-tetradecanoylphorbol 13-acetate A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types. LINCS:LSM-25630 PMID:20333698 PMID:25918710 PMID:34234780 CHEBI:746 CHEBI:745 PMID:33291656 KNApSAcK:C00003491 Wikipedia:12-O-Tetradecanoylphorbol-13-acetate PMID:30248704 PMCID:PMC6898309 CAS:16561-29-8 Beilstein:2407201 PMID:16740769 tetradecanoylphorbol acetate acetate ester carcinogenic agent diester mitogen protein kinase C agonist apoptosis inducer reactive oxygen species generator plant metabolite tetradecanoate ester