Compound: Phorbol 12-myristate 13-acetate
SMILES: O=C1C(=C[C@@H]2[C@]1(O)CC(=C[C@@H]3[C@]2(O)[C@@H]([C@@H](OC(=O)CCCCCCCCCCCCC)[C@@]4([C@H]3C4(C)C)OC(=O)C)C)CO)C
InChIKey: PHEDXBVPIONUQT-RGYGYFBISA-N
Synonyms: Phorbol 12-myristate 13-acetate, 16561-29-8, phorbol-12-myristate-13-acetate, 12-O-Tetradecanoylphorbol-13-acetate, 12-O-Tetradecanoylphorbol 13-acetate, Tetradecanoylphorbol acetate, Factor A1, Phorbol myristate acetate, phorbol 13-acetate 12-myristate, Phorbol 12-tetradecanoate 13-acetate, PMA (tumor promoter), TPA (phorbol derivative), 13-O-Acetylphorbol 12-myristate, Pma (phorbol ester), Tpa (phorbol ester), 12-Tetradecanoylphorbol 13-monoacetate, Phorbol monoacetate monomyristate, 4beta-Phorbol 12-myristate 13-acetate, Phorbol-myristate acetate, Phorbol 12-myristate 13-acetate diester, Phorbol acetate, myristate, 12-O-Tetradecanoyl phorbol acetate, beta-Phorbol 12-myristate 13-acetate, NSC 262244, 13-Tetradecanoylphorbol acetate, NI40JAQ945, DTXSID5023798, Phorbol-12-myristate 13-acetate, 12-Tetradecanoylphorbol-13-acetate, 12-o-Tetradekanoylphorbol-13-acetat, NSC-262244, 4beta-Phorbol-12-myristate-13-acetate, CHEBI:37537, NSC262244, Pentahydroxy-tigliadienone-monoacetate(c)monomyristate(b), Tetradecanoic acid, 9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1H-cyclopropa(3,4)benz(1,2-e)azulen-9-yl ester, (1aR-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-, 5H-Cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1a-beta,1b-alpha,4,4a,7a-beta,7b,8,9,9a-decahydro-4a-alpha,7b-beta,9-alpha,9a-beta-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-beta-tetramethyl-, 9a-acetate 9-myristate, Myristic acid, 9-ester with 1,1aalpha,1bbeta,4,4a,7aalpha,7b,8,9,9a-decahydro-4abeta,7balpha,9beta,9aalpha-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8alpha-tetramethyl-5H-cyclopropa(3,4)benz(1,2-e)azulen-5-one 9a-acetate, (+)-, [(1S,2S,6R,10S,11R,13S,14R,15R)-13-acetyloxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] tetradecanoate, Myristic acid, 9-ester with 1,1a-alpha,1b-beta,4,4a,7a-alpha,7b,8,9,9a-decahydro-4a-beta,7b-alpha,9-beta,9a-alpha-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-alpha-tetramethyl-5H-cyclopropa(3,4)benz(1,2-e)azulen-5-one, 9a-acetate, Acetate, Phorbol Myristate, Myristate Acetate, Phorbol, Acetate, Tetradecanoylphorbol, 12 Myristoyl 13 acetylphorbol, 12-Myristoyl-13-acetylphorbol, ((1S,2S,6R,10S,11R,13S,14R,15R)-13-acetyloxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo(8.5.0.02,6.011,13)pentadeca-3,8-dienyl) tetradecanoate, (1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo(8.5.0.0^(2,6).0^(11,13))pentadeca-3,8-dien-14-yl tetradecanoate, (1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-14-yl tetradecanoate, 12 O Tetradecanoyl Phorbol 13 Acetate, 12-O-Tetradecanoyl Phorbol 13-Acetate, 13-Acetate, 12-O-Tetradecanoyl Phorbol, Phorbol 13-Acetate, 12-O-Tetradecanoyl, RefChem:929146, DTXCID30819884, Tetradecanoylphorbol Acetate, 4a alpha, Phorbol ester, 12-Tetradecanoylphorbol 13-acetate, MFCD00036736, CCRIS 716, HSDB 3542, CHEMBL279115, (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, Tetradecanoic acid, (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1H-cyclopropa[3,4]benz[1,2-e]azulen-9-yl ester, Phorbol 12-myristate 13-acetate (PMA), C36H56O8, 12-o-tetradecanoyl-phorbol-13-acetate, yristate, UNII-NI40JAQ945, NSC626496, -yl ester, tetradecanoyl-beta-phorbol acetate, BRN 2407201, SpecPlus_000801, Spectrum2_001911, Spectrum4_000889, Spectrum5_001855, MolMap_000041, UPCMLD-DP069, 12-O-Tetradekanoylphorbol-13-acetat [German], BIDD:PXR0145, CBiol_002014, BSPBio_001024, KBioGR_000364, KBioGR_001298, KBioSS_000364, SPECTRUM330004, DivK1c_006897, SPBio_001902, 1H-Cyclopropa[3,4]benz[1,2-e]azulene, tetradecanoic acid deriv., GTPL2341, orb1296136, [acetoxy-dihydroxy-(hydroxymethyl)-tetramethyl-oxo-[?]yl] tetradecanoate, SCHEMBL29353795, UPCMLD-DP069:001, UPCMLD-DP069:002, BCBcMAP01_000182, KBio1_001841, KBio2_000364, KBio2_002932, KBio2_005500, KBio3_000707, KBio3_000708, Bio1_000300, Bio1_000789, Bio1_001278, Bio2_000352, Bio2_000832, HMS1362D05, HMS1792D05, HMS1990D05, HMS3403D05, Phorbol 13 Acetate 12 Myristate, BNB65429, EX-A6920, -one 9a-acetate, (+)- (8CI), BDBM50099066, CCG-39863, HB0502, NSC262644, AKOS024418767, CS-6053, EBC-378042, FP15184, FS-4842, LMPR0104330002, NSC-262644, NSC-626496, IDI1_002107, NCGC00161633-01, NCGC00161633-04, NCGC00161633-05, 4-.beta.-Phorbol 12-myristate 13-OAc, AC-33957, DA-49086, HY-18739, Tetradecanoic acid, 9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9, 9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1H-cyclopropa(3,4)benz(1,2-e)azulen-9-yl ester, (1aR-(1aa,1bb,4ab,7aa,7ba, 8a,9b,9aa))-, Phorbol 12-myristate 13-acetate (PMA)?, 12-o-tetradecanoylphorbol-13-acetate (tpa), NS00025422, P1585, PHORBOL-12-TETRADECANOYL-13-ACETATE, C05151, M02249, 4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha)]-, Q416716, 12-O-TETRADECANOYLPHORBOL-13-ACETATE [HSDB], BRD-K68552125-001-03-8, BRD-K68552125-001-04-6, BRD-K68552125-001-05-3, PHORBOL 12-MYRISTATE 13-ACETATE DIESTER [MI], Phorbol-12-myristate-13-acetate - CAS 16561-29-8, Phorbol 12-myristate 13-acetate, synthetic, >=98.0% (TLC), PMA, for use in molecular biology applications, >=99% (TLC), Phorbol 12-myristate 13-acetate, >=99% (TLC), film or powder, 12-O-tetradecanoyl phorbol-13-acetate;Cocarcinogen A1; Cocarcinogen C3, (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-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, [(1S,2S,6R,10S,11R,13S,14R,15R)-13-acetoxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] tetradecanoate, 11016-13-0, 5H-Cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1a-beta,1b-alpha,4,4a,7a-beta,7b,8,9,9a-decahydro-4a-alpha,7b-beta,9-alpha,9a-beta-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-beta-tetramethyl-, 9a-acetate 9-m, Myristic acid, 9-ester with 1,1aalpha,1bbeta,4,4a,7aalpha,7b,8,9,9a-decahydro-4abeta,7balpha,9beta,9aalpha-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8alpha-tetramethyl-5H-cyclopropa[3,4]benz[1,2-e]azulen-5, tetradecanoic acid, (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1H-cyclopropa[3,4]benz[1,2-e]azulen-9, Tetradecanoic acid, 9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1H-cyclopropa[3,4]benz[1,2-e]azulen-9-yl ester, [1aR-(1aalpha,1bbeta,
Theoretical properties:
molecular_formula: C36H56O8
molecular_weight: 616.8 g/mol
exact_mass: 616.39751874 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 8
rotatable_bond_count: 17
heavy_atom_count: 44
topological_polar_surface_area: 130 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Oil
color: Oil
melting_point: 162 °F (NTP, 1992)
solubility: Practically insoluble (NTP, 1992)
Descriptions:
{"pubchem": "Phorbol 13-acetate 12-myristate is 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. It has a role as an antineoplastic agent, a carcinogenic agent, a mitogen, a protein kinase C agonist, an apoptosis inducer, a reactive oxygen species generator and a plant metabolite. It is a tertiary alpha-hydroxy ketone, a phorbol ester, an acetate ester, a diester and a tetradecanoate ester.", "chebi": "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.", "chembl": "PHORBOL MYRISTATE ACETATE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.", "wikipedia": "Phorbol-12-myristate-13-acetate-induced protein 1 is a protein that in humans is encoded by the PMAIP1 gene, and is also known as Noxa.\nNoxa (Latin for damage) is a pro-apoptotic member of the Bcl-2 protein family. Bcl-2 family members can form hetero- or homodimers, and they act as anti- or pro-apoptotic regulators that are involved in a wide variety of cellular activities. The expression of Noxa is regulated by the tumor suppressor p53, and Noxa has been shown to be involved in p53-mediated apoptosis."}