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13-Acetylphorbol

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID f2b77262-531a-4d25-a14b-701ac01822ad
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)-1,6,14-trihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-13-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] acetate
SMILES (Canonical) CC1C(C2(C(C2(C)C)C3C1(C4C=C(C(=O)C4(CC(=C3)CO)O)C)O)OC(=O)C)O
SMILES (Isomeric) C[C@@H]1[C@H]([C@@]2([C@@H](C2(C)C)[C@H]3[C@]1([C@@H]4C=C(C(=O)[C@]4(CC(=C3)CO)O)C)O)OC(=O)C)O
InChI InChI=1S/C22H30O7/c1-10-6-15-20(27,17(10)25)8-13(9-23)7-14-16-19(4,5)22(16,29-12(3)24)18(26)11(2)21(14,15)28/h6-7,11,14-16,18,23,26-28H,8-9H2,1-5H3/t11-,14+,15-,16-,18-,20-,21-,22-/m1/s1
InChI Key SDSVJYOOAPRSDA-RPCQODIISA-N
Popularity 46 references in papers

Physical and Chemical Properties

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Molecular Formula C22H30O7
Molecular Weight 406.50 g/mol
Exact Mass 406.19915329 g/mol
Topological Polar Surface Area (TPSA) 124.00 Ų
XlogP -0.30
Atomic LogP (AlogP) 0.50
H-Bond Acceptor 7
H-Bond Donor 4
Rotatable Bonds 2

Synonyms

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Phorbol 13-acetate
Phorbol-13-acetate
Phorbol 13-monoacetate
32752-29-7
Phorbol 12-Monoacetate
CHEBI:45127
Phorbol13-acetate
(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9-trihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-9aH-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl acetate
[(1S,2S,6R,10S,11R,13S,14R,15R)-1,6,14-trihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-13-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] acetate
5H-Cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1a-alpha,1b-beta,4,4a,7a-alpha,7b,8,9,9a-decahydro-4a-alpha,7b-alpha,9-beta,9a-alpha-tetrahydroxy-3-hydroxymethyl-1,1,6,8-alpha-tetramethyl-, 9a-acetate
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of 13-Acetylphorbol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9439 94.39%
Caco-2 - 0.7738 77.38%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.7083 70.83%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8705 87.05%
OATP1B3 inhibitior + 0.9307 93.07%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.8083 80.83%
P-glycoprotein inhibitior - 0.9166 91.66%
P-glycoprotein substrate - 0.5883 58.83%
CYP3A4 substrate + 0.6411 64.11%
CYP2C9 substrate - 0.8151 81.51%
CYP2D6 substrate - 0.9121 91.21%
CYP3A4 inhibition - 0.8718 87.18%
CYP2C9 inhibition - 0.6084 60.84%
CYP2C19 inhibition - 0.8804 88.04%
CYP2D6 inhibition - 0.9221 92.21%
CYP1A2 inhibition - 0.8571 85.71%
CYP2C8 inhibition - 0.7122 71.22%
CYP inhibitory promiscuity - 0.8095 80.95%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6700 67.00%
Eye corrosion - 0.9878 98.78%
Eye irritation - 0.9296 92.96%
Skin irritation - 0.6864 68.64%
Skin corrosion - 0.9399 93.99%
Ames mutagenesis - 0.5474 54.74%
Human Ether-a-go-go-Related Gene inhibition - 0.4570 45.70%
Micronuclear - 0.7100 71.00%
Hepatotoxicity - 0.5833 58.33%
skin sensitisation - 0.7441 74.41%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity - 0.5646 56.46%
Acute Oral Toxicity (c) III 0.5415 54.15%
Estrogen receptor binding + 0.6562 65.62%
Androgen receptor binding + 0.6969 69.69%
Thyroid receptor binding + 0.6073 60.73%
Glucocorticoid receptor binding + 0.6617 66.17%
Aromatase binding + 0.7394 73.94%
PPAR gamma - 0.5413 54.13%
Honey bee toxicity - 0.8356 83.56%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6400 64.00%
Fish aquatic toxicity + 0.8546 85.46%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.89% 96.09%
CHEMBL2581 P07339 Cathepsin D 95.03% 98.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.17% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.13% 91.11%
CHEMBL1937 Q92769 Histone deacetylase 2 88.31% 94.75%
CHEMBL2996 Q05655 Protein kinase C delta 87.02% 97.79%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.05% 94.45%
CHEMBL4208 P20618 Proteasome component C5 85.70% 90.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.63% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.23% 95.56%
CHEMBL299 P17252 Protein kinase C alpha 83.05% 98.03%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.33% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.01% 100.00%
CHEMBL4794 Q8NER1 Vanilloid receptor 81.52% 98.97%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.43% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.89% 94.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.30% 93.04%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Aquilaria sinensis
Croton tiglium

Cross-Links

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PubChem 499953
NPASS NPC156252
LOTUS LTS0199896
wikiData Q27095178