isoprenoid phorbol 13-acetate 12-myristate 0 616.39752 616.836 pubmed:36419617 pubmed:15721302 pubmed:27676154 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 <em>Croton tiglium</em>. 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. pubmed:26894087 chebi_ontology 12-tetradecanoylphorbol 13-acetate pubmed:29872754 pubmed:31256364 CHEBI:37537 pubmed:25649981 pubmed:35457039 phorbol-12-myristate-13-acetate (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 phorbol 12-tetradecanoate 13-acetate pubmed:2866623 [H][C@@]12C=C(C)C(=O)[C@@]1(O)CC(CO)=C[C@]1([H])[C@]2(O)[C@H](C)[C@@H](OC(=O)CCCCCCCCCCCCC)[C@@]2(OC(C)=O)C(C)(C)[C@@]12[H] pubmed:36671729 pubmed:33268675 (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 pubmed:29538403 pubmed:29385060 PMA pubmed:29933732 metacyc.compound:CPD-19636 pubmed:33254440 pubmed:30663866 pubmed:3593207 pubmed:18541361 lipidmaps:LMPR0104330002 pubmed:38474055 wikipedia.en:12-O-Tetradecanoylphorbol-13-acetate phorbol 12-myristate 13-acetate lincs.smallmolecule:LSM-25630 pubmed:37588597 C36H56O8 PHEDXBVPIONUQT-RGYGYFBISA-N 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 pubmed:31019367 pubmed:15822940 TPA pubmed:30075941 chemspider:25977 pubmed:30254419 pubmed:37114178 pubmed:34890758 pubmed:38004599 pubmed:26826276 pubmed:35259405 pubmed:12421969 beilstein:2407201 pubmed:33291656 kegg.compound:C05151 12-O-tetradecanoylphorbol 13-acetate pubmed:34234780 pubmed:36618426 pubmed:20333698 cas:16561-29-8 pubmed:30248704 hmdb:HMDB0244744 pubmed:16740769 CHEBI:746 CHEBI:745 pubmed:31194000 pubmed:22696070 pubmed:31437790 knapsack:C00003491 pubmed:34645824 pubmed:25918710 pubmed:31904021 pmc:PMC6898309 pubmed:27315825 pubmed:32140039 tetradecanoylphorbol acetate pubmed:29291631