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12-O-tetradecanoylphorbol-13-acetate
- Family: Plantae - Euphorbiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Phorbol Diterpenoid
| Canonical 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 |
| InChIKey | PHEDXBVPIONUQT-RGYGYFBISA-N |
| Formula | C36H56O8 |
| HBA | 8 |
| HBD | 3 |
| MW | 616.84 |
| Rotatable Bonds | 15 |
| TPSA | 130.36 |
| LogP | 5.75 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 44 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.81 |
| Exact Mass | 616.4 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Croton tiglium | Euphorbiaceae | Plantae | 497687 |
Showing of synonyms
12-O-tetradecanoylphorbol-13-acetate
Phorbol 12-myristate 13-acetate
16561-29-8
Phorbol-12-myristate-13-acetate
12-O-Tetradecanoylphorbol 13-acetate
Tetradecanoylphorbol acetate
Phorbol ester
Factor A1
12-Tetradecanoylphorbol 13-acetate
Phorbol myristate acetate
Phorbol 13-acetate 12-myristate
TPA
PMA
PMA (tumor promoter)
Phorbol 12-tetradecanoate 13-acetate
TPA (phorbol derivative)
MFCD00036736
CCRIS 716
Pma (phorbol ester)
Tpa (phorbol ester)
Phorbol 12-myristate 13-acetate diester
Phorbol monoacetate monomyristate
HSDB 3542
13-O-Acetylphorbol 12-myristate
12-O-Tetradecanoyl phorbol acetate
Beta-Phorbol 12-myristate 13-acetate
NSC 262244
12-Tetradecanoylphorbol 13-monoacetate
4beta-Phorbol 12-myristate 13-acetate
CHEMBL279115
NI40JAQ945
(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
CHEBI:37537
NSC-262244
Phorbol 12-myristate 13-acetate (PMA)
Phorbol acetate, myristate
12-o-Tetradekanoylphorbol-13-acetat
[(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
Phorbol-myristate acetate
Pentahydroxy-tigliadienone-monoacetate(c)monomyristate(b)
Yristate
UNII-NI40JAQ945
13-Tetradecanoylphorbol acetate
NSC626496
-yl ester
Phorbol-12-myristate 13-acetate
Tetradecanoyl-beta-phorbol acetate
12-Tetradecanoylphorbol-13-acetate
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
12-o-tetradecanoyl-phorbol-13-acetate
4beta-Phorbol-12-myristate-13-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
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))-
DivK1c_006897
SCHEMBL115567
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
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
NSC262244
NSC262644
AKOS024418767
CS-6053
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
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))-
Phorbol 12-myristate 13-acetate (PMA)?
12-o-tetradecanoylphorbol-13-acetate (tpa)
NS00025422
P1585
PHORBOL-12-TETRADECANOYL-13-ACETATE
C05151
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
(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
11016-13-0
4beta,9alpha,12beta,13alpha,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate
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,
Pubchem:
27924
Cas:
16561-29-8
Gnps:
CCMSLIB00000478105
Zinc:
ZINC000008214783
Kegg Ligand:
C05151
Chebi:
37537
Nmrshiftdb2:
70002000
Metabolights:
MTBLC37537
Chembl:
CHEMBL279115
Comptox:
DTXSID5023798
Drugbank:
DB17045
CPRiL:
26
SMILES: C12C(C1)CCC3C4C(C(=O)C=C4)CC=CC23
Level: 0
Mol. Weight: 616.84 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.93
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.7
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 6.32
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.04
- Plasma Protein Binding
- 102.22
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 6.61
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.32
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.44
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.97
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -15943.53
- Rat (Acute)
- 3.59
- Rat (Chronic Oral)
- 2.59
- Fathead Minnow
- 36.75
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 304.56
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 4.27
- Log(P)
- 7.48
- Log S
- -4.76
- Log(Vapor Pressure)
- -12.42
- Melting Point
- 135.29
- pKa Acid
- 6.28
- pKa Basic
- 2.62
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.8489 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.8489 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8433 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8433 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7972 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7972 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7558 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7558 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7510 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7510 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7197 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7197 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7162 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7162 |
| Ferric enterobactin-binding periplasmic protein FepB | P0AEL6 | FEPB_ECOLI | Escherichia coli | 3 | 0.7151 |
| Ferric enterobactin-binding periplasmic protein FepB | P0AEL6 | FEPB_ECOLI | Escherichia coli | 3 | 0.7151 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7127 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7127 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7101 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7101 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7096 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7096 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7016 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7016 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7011 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7011 |