Phorbol acetate, caprate

Details

• Internal ID: a90f58d2-a062-46c8-8724-2fc67651416d
• 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)-14-acetyloxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-13-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] decanoate
• SMILES (Canonical): CCCCCCCCCC(=O)OC12C(C1(C)C)C3C=C(CC4(C(C3(C(C2OC(=O)C)C)O)C=C(C4=O)C)O)CO
• SMILES (Isomeric): CCCCCCCCCC(=O)O[C@@]12[C@@H](C1(C)C)[C@@H]3C=C(C[C@]4([C@H]([C@]3([C@@H]([C@H]2OC(=O)C)C)O)C=C(C4=O)C)O)CO
• InChI: InChI=1S/C32H48O8/c1-7-8-9-10-11-12-13-14-25(35)40-32-26(29(32,5)6)23-16-22(18-33)17-30(37)24(15-19(2)27(30)36)31(23,38)20(3)28(32)39-21(4)34/h15-16,20,23-24,26,28,33,37-38H,7-14,17-18H2,1-6H3/t20-,23+,24-,26-,28-,30-,31-,32-/m1/s1
• InChI Key: CSJWNHJJHIAAIG-SVOQZPEWSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₈O₈
• Molecular Weight: 560.70 g/mol
• Exact Mass: 560.33491849 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.19
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 11

Synonyms

• 20839-15-0
• [(1S,2S,6R,10S,11R,13S,14R,15R)-14-acetyloxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-13-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] decanoate
• ((1S,2S,6R,10S,11R,13S,14R,15R)-14-acetyloxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-13-tetracyclo(8.5.0.02,6.011,13)pentadeca-3,8-dienyl) decanoate
• RefChem:908074
• Phorbol acetate, caprate
• 16561-28-7
• 12-O-Acetyl-phorbol-13-decanoate
• BRN 2610782
• CHEMBL2375785
• Phorbol monoacetate monodecanoate
• DTXSID40937109
• 12-O-Acetylphorbol 13-decanoate
• Phorbol 12-acetate 13-decanoate
• Decanoic acid, 9a-ester with 1,1a-alpha,1b-beta,4,4a,7a-alpha,7b,8,9,9a-decahydro-3-(hydroxymethyl)-4a-beta,7b-alpha,9-beta,9a-alpha-tetrahydroxy-1,1,6,8-alpha-tetramethyl-5H-cyclopropa(3,4)benz(1,2-e)azulen-5-one 9-acetate
• Decanoic acid, ester with phorbol acetate
• [acetoxy-dihydroxy-(hydroxymethyl)-tetramethyl-oxo-[?]yl] decanoate
• (1aR)-1,1,6,8alpha-Tetramethyl-3-(hydroxymethyl)-5-oxo-1,1aalpha,1bbeta,4,4a,7aalpha,7b,8,9,9a-decahydro-5H-cyclopr
• 28878-88-8
• 5H-Cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-, monoacetate monodecanoate
• 9-(Acetyloxy)-4a,7b-dihydroxy-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 decanoate
• Decanoic acid, (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9-(acetyloxy)-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-9aH-cyclopropa[3,4]benz[1,2-e]azulen-9a-yl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9816	98.16%
Caco-2	-	0.7539	75.39%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7776	77.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8174	81.74%
OATP1B3 inhibitior	+	0.9222	92.22%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.6275	62.75%
BSEP inhibitior	+	0.9306	93.06%
P-glycoprotein inhibitior	+	0.8033	80.33%
P-glycoprotein substrate	+	0.6404	64.04%
CYP3A4 substrate	+	0.6755	67.55%
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	+	0.6270	62.70%
CYP inhibitory promiscuity	-	0.8148	81.48%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7029	70.29%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9211	92.11%
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	-	0.3896	38.96%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.5592	55.92%
skin sensitisation	-	0.8776	87.76%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6532	65.32%
Acute Oral Toxicity (c)	III	0.4712	47.12%
Estrogen receptor binding	+	0.6970	69.70%
Androgen receptor binding	+	0.7165	71.65%
Thyroid receptor binding	-	0.5347	53.47%
Glucocorticoid receptor binding	+	0.7388	73.88%
Aromatase binding	+	0.7383	73.83%
PPAR gamma	+	0.5947	59.47%
Honey bee toxicity	-	0.8534	85.34%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.7276	72.76%
Fish aquatic toxicity	+	0.9894	98.94%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2996	Q05655	Protein kinase C delta	98.92%	97.79%
CHEMBL299	P17252	Protein kinase C alpha	98.72%	98.03%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.26%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.21%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.65%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.17%	91.11%
CHEMBL3045	P05771	Protein kinase C beta	94.36%	97.63%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.99%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.23%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.18%	86.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	89.14%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	88.23%	92.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.20%	91.24%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.60%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.79%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.12%	93.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.20%	100.00%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	83.09%	97.29%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	82.23%	91.81%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	81.89%	85.94%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.16%	93.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.88%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.74%	100.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.37%	90.08%

Plants that contains it

• Croton tiglium

Cross-Links

• PubChem: 124027
• NPASS: NPC255081
• LOTUS: LTS0096867
• wikiData: Q82913314