Phorbol 12-myristate 13-acetate

Details

• Internal ID: 8c821af8-22ef-4276-b10f-28c78b1413a7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Tigliane and ingenane diterpenoids > Phorbol esters
• IUPAC Name: [(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
• SMILES (Canonical): CCCCCCCCCCCCCC(=O)OC1C(C2(C(C=C(CC3(C2C=C(C3=O)C)O)CO)C4C1(C4(C)C)OC(=O)C)O)C
• SMILES (Isomeric): CCCCCCCCCCCCCC(=O)O[C@@H]1[C@H]([C@]2([C@@H](C=C(C[C@]3([C@H]2C=C(C3=O)C)O)CO)[C@H]4[C@@]1(C4(C)C)OC(=O)C)O)C
• 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
• Popularity: 40,580 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₆O₈
• Molecular Weight: 616.80 g/mol
• Exact Mass: 616.39751874 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 6.50
• Atomic LogP (AlogP): 5.75
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 15

Synonyms

• 16561-29-8
• 12-O-Tetradecanoylphorbol-13-acetate
• phorbol-12-myristate-13-acetate
• 12-O-Tetradecanoylphorbol 13-acetate
• Phorbol ester
• Tetradecanoylphorbol acetate
• Factor A1
• 12-Tetradecanoylphorbol 13-acetate
• Phorbol myristate acetate
• phorbol 13-acetate 12-myristate
• PMA
• PMA (tumor promoter)
• Phorbol 12-tetradecanoate 13-acetate
• TPA (phorbol derivative)
• CCRIS 716
• Pma (phorbol ester)
• TPA
• Tpa (phorbol ester)
• Phorbol 12-myristate 13-acetate (PMA)
• Phorbol 12-myristate 13-acetate diester
• Phorbol monoacetate monomyristate
• HSDB 3542
• 13-O-Acetylphorbol 12-myristate
• 12-O-Tetradecanoyl phorbol acetate
• C36H56O8
• Phorbol-myristate acetate
• beta-Phorbol 12-myristate 13-acetate
• NSC 262244
• 12-Tetradecanoylphorbol 13-monoacetate
• 4beta-Phorbol 12-myristate 13-acetate
• UNII-NI40JAQ945
• CHEMBL279115
• NI40JAQ945
• 13-Tetradecanoylphorbol acetate
• CHEBI:37537
• Phorbol-12-myristate 13-acetate
• tetradecanoyl-beta-phorbol acetate
• 12-Tetradecanoylphorbol-13-acetate
• 12-o-Tetradekanoylphorbol-13-acetat
• NSC-262244
• (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
• 12-o-tetradecanoyl-phorbol-13-acetate
• 4beta-Phorbol-12-myristate-13-acetate
• BRN 2407201
• Phorbol acetate, myristate
• 12-O-Tetradekanoylphorbol-13-acetat [German]
• 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))-
• 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, (+)-
• 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
• 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))-
• MFCD00036736
• Pentahydroxy-tigliadienone-monoacetate(c)monomyristate(b)
• yristate
• NSC626496
• Cocarcinogen A1
• Cocarcinogen C3
• -yl ester
• C36-H56-O8
• 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
• SpecPlus_000801
• Spectrum2_001911
• Spectrum4_000889
• Spectrum5_001855
• D09DHT
• MolMap_000041
• UPCMLD-DP069
• BIDD:PXR0145
• CBiol_002014
• BSPBio_001024
• KBioGR_000364
• KBioGR_001298
• KBioSS_000364
• SPECTRUM330004
• DivK1c_006897
• SCHEMBL115567
• phorbol12-myristate13-acetate
• SPBio_001902
• 1H-Cyclopropa[3,4]benz[1,2-e]azulene, tetradecanoic acid deriv.
• GTPL2341
• [acetoxy-dihydroxy-(hydroxymethyl)-tetramethyl-oxo-[?]yl] tetradecanoate
• DTXSID5023798
• UPCMLD-DP069:001
• UPCMLD-DP069:002
• BCBcMAP01_000182
• KBio1_001841
• KBio2_000364
• KBio2_002932
• KBio2_005500
• KBio3_000707
• KBio3_000708
• PHEDXBVPIONUQT-RGYGYFBISA-N
• Bio1_000300
• Bio1_000789
• Bio1_001278
• Bio2_000352
• Bio2_000832
• HMS1362D05
• HMS1792D05
• HMS1990D05
• HMS3403D05
• Phorbol 13 Acetate 12 Myristate
• EX-A6920
• 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-(1a.alpha.,1b.beta.,4a.beta.,7a.alpha.,7b.alpha.,8.alpha.,9.beta.,9a.alpha.)]-
• -one 9a-acetate, (+)- (8CI)
• BDBM50099066
• CCG-39863
• HB0502
• NSC262244
• NSC262644
• s7791
• AKOS024418767
• CS-6053
• FS-4842
• LMPR0104330002
• NSC-262644
• NSC-626496
• IDI1_002107
• NCGC00161633-01
• NCGC00161633-04
• NCGC00161633-05
• 4-.beta.-Phorbol 12-myristate 13-OAc
• AC-33957
• HY-18739
• 12-o-tetradecanoylphorbol-13-acetate (tpa)
• P1585
• PHORBOL-12-TETRADECANOYL-13-ACETATE
• C05151
• 4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha)]-
• Q416716
• W-201494
• 12-O-TETRADECANOYLPHORBOL-13-ACETATE [HSDB]
• BRD-K68552125-001-03-8
• BRD-K68552125-001-04-6
• 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)-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 tetradecanoate
• (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 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-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 1,1a.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, ()-
• 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,

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9816	98.16%
Caco-2	-	0.8039	80.39%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7776	77.76%
OATP2B1 inhibitior	-	0.5766	57.66%
OATP1B1 inhibitior	+	0.8317	83.17%
OATP1B3 inhibitior	+	0.9222	92.22%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.6275	62.75%
BSEP inhibitior	+	0.8755	87.55%
P-glycoprotein inhibitior	+	0.7761	77.61%
P-glycoprotein substrate	+	0.6647	66.47%
CYP3A4 substrate	+	0.6726	67.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9180	91.80%
CYP3A4 inhibition	-	0.6727	67.27%
CYP2C9 inhibition	+	0.8939	89.39%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	+	0.6229	62.29%
CYP inhibitory promiscuity	-	0.8148	81.48%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7029	70.29%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9114	91.14%
Skin irritation	+	0.4927	49.27%
Skin corrosion	-	0.9520	95.20%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4261	42.61%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.5033	50.33%
skin sensitisation	-	0.8776	87.76%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6658	66.58%
Acute Oral Toxicity (c)	III	0.4712	47.12%
Estrogen receptor binding	+	0.7486	74.86%
Androgen receptor binding	+	0.7165	71.65%
Thyroid receptor binding	-	0.5660	56.60%
Glucocorticoid receptor binding	+	0.6688	66.88%
Aromatase binding	+	0.6763	67.63%
PPAR gamma	+	0.5984	59.84%
Honey bee toxicity	-	0.8428	84.28%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.7376	73.76%
Fish aquatic toxicity	+	0.9894	98.94%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293224	P10636	Microtubule-associated protein tau	19952.6 nM	Potency	via CMAUP
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	10 nM	Potency	via Super-PRED
CHEMBL299	P17252	Protein kinase C alpha	2.5 nM; 2.5 nM; 6.4 nM	Ki; Ki; Ki	PMID: 11327599; via Super-PRED; PMID: 21596562
CHEMBL3045	P05771	Protein kinase C beta	1.8 nM; 1.8 nM	Ki; Ki	via Super-PRED; PMID: 11327599
CHEMBL2996	Q05655	Protein kinase C delta	0.8 nM; 0.8 nM	Ki; Ki	via Super-PRED; PMID: 11327599
CHEMBL3582	Q02156	Protein kinase C epsilon	0.45 nM; 0.45 nM	Ki; Ki	via Super-PRED; PMID: 11327599
CHEMBL2938	P05129	Protein kinase C gamma	4.9 nM; 4.9 nM	Ki; Ki	PMID: 11327599; via Super-PRED
CHEMBL3920	Q04759	Protein kinase C theta	3190 nM	EC50	PMID: 20100661
CHEMBL1293232	Q16637	Survival motor neuron protein	15.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.33%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.85%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.70%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.97%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.71%	94.45%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	88.34%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	87.87%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.53%	99.17%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.04%	91.24%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.99%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.79%	95.56%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	82.84%	91.81%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.70%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.61%	93.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.47%	100.00%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	81.26%	85.94%
CHEMBL4794	Q8NER1	Vanilloid receptor	81.09%	98.97%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	80.68%	97.29%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.43%	90.08%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.41%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.25%	93.56%

Plants that contains it

• Chaenomeles sinensis
• Croton alnifolius
• Croton tiglium
• Elsholtzia bodinieri
• Euphorbia turczaninowii
• Euphorbia wallichii
• Silybum marianum
• Trigonostemon howii
• Vincetoxicum hirsutum
• Wisteria brachybotrys
• Wisteria brachybotrys

Cross-Links

• PubChem: 27924
• NPASS: NPC5989
• ChEMBL: CHEMBL279115
• LOTUS: LTS0029561
• wikiData: Q416716