[(1S,2R,6R,10R,11S,13S,14R,15R)-13-acetyloxy-1,6,14-trihydroxy-4,12,12,15-tetramethyl-5-oxo-8-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl]methyl (9Z,12Z)-octadeca-9,12-dienoate

Details

• Internal ID: 93ec6efb-7df1-4847-901c-36e94dc97e9e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Tigliane and ingenane diterpenoids > Phorbol esters
• IUPAC Name: [(1S,2R,6R,10R,11S,13S,14R,15R)-13-acetyloxy-1,6,14-trihydroxy-4,12,12,15-tetramethyl-5-oxo-8-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl]methyl (9Z,12Z)-octadeca-9,12-dienoate
• SMILES (Canonical): CCCCCC=CCC=CCCCCCCCC(=O)OCC1=CC2C3C(C3(C(C(C2(C4C=C(C(=O)C4(C1)O)C)O)C)O)OC(=O)C)(C)C
• SMILES (Isomeric): CCCCC/C=C\C/C=C\CCCCCCCC(=O)OCC1=C[C@@H]2[C@@H]3[C@](C3(C)C)([C@@H]([C@H]([C@@]2([C@H]4C=C(C(=O)[C@]4(C1)O)C)O)C)O)OC(=O)C
• InChI: InChI=1S/C40H60O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-33(42)47-26-30-24-31-34-37(5,6)40(34,48-29(4)41)36(44)28(3)39(31,46)32-23-27(2)35(43)38(32,45)25-30/h11-12,14-15,23-24,28,31-32,34,36,44-46H,7-10,13,16-22,25-26H2,1-6H3/b12-11-,15-14-/t28-,31-,32+,34+,36-,38-,39-,40-/m1/s1
• InChI Key: YSXDURFMHDUCMP-DWXACDDLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₀O₈
• Molecular Weight: 668.90 g/mol
• Exact Mass: 668.42881887 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 7.10
• Atomic LogP (AlogP): 6.87
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 17

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9788	97.88%
Caco-2	-	0.8269	82.69%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7542	75.42%
OATP2B1 inhibitior	-	0.8579	85.79%
OATP1B1 inhibitior	+	0.7402	74.02%
OATP1B3 inhibitior	+	0.9595	95.95%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6635	66.35%
BSEP inhibitior	+	0.9765	97.65%
P-glycoprotein inhibitior	+	0.7615	76.15%
P-glycoprotein substrate	+	0.6114	61.14%
CYP3A4 substrate	+	0.7049	70.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9170	91.70%
CYP3A4 inhibition	-	0.8046	80.46%
CYP2C9 inhibition	+	0.7335	73.35%
CYP2C19 inhibition	-	0.8899	88.99%
CYP2D6 inhibition	-	0.9128	91.28%
CYP1A2 inhibition	-	0.8811	88.11%
CYP2C8 inhibition	+	0.6812	68.12%
CYP inhibitory promiscuity	-	0.8208	82.08%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6675	66.75%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9157	91.57%
Skin irritation	+	0.5534	55.34%
Skin corrosion	-	0.9515	95.15%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6733	67.33%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8304	83.04%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.7199	71.99%
Acute Oral Toxicity (c)	III	0.4515	45.15%
Estrogen receptor binding	+	0.8168	81.68%
Androgen receptor binding	+	0.7289	72.89%
Thyroid receptor binding	-	0.5104	51.04%
Glucocorticoid receptor binding	+	0.7306	73.06%
Aromatase binding	+	0.6036	60.36%
PPAR gamma	+	0.6601	66.01%
Honey bee toxicity	-	0.8335	83.35%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.8500	85.00%
Fish aquatic toxicity	+	0.9932	99.32%

Targets

Proven Targets:

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	98.27%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.00%	98.95%
CHEMBL299	P17252	Protein kinase C alpha	97.32%	98.03%
CHEMBL2996	Q05655	Protein kinase C delta	96.71%	97.79%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.43%	99.17%
CHEMBL3045	P05771	Protein kinase C beta	93.50%	97.63%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.59%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.77%	86.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	90.22%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.11%	97.25%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.96%	96.95%
CHEMBL221	P23219	Cyclooxygenase-1	89.81%	90.17%
CHEMBL1937	Q92769	Histone deacetylase 2	89.55%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.43%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.91%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	87.22%	92.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.18%	99.23%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	86.60%	85.94%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.47%	97.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.74%	95.56%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	85.47%	92.08%
CHEMBL5103	Q969S8	Histone deacetylase 10	85.45%	90.08%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.71%	97.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.40%	100.00%
CHEMBL325	Q13547	Histone deacetylase 1	82.41%	95.92%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.88%	93.00%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	81.78%	91.81%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	81.34%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.77%	100.00%

Plants that contains it

• Croton tiglium

Cross-Links

• PubChem: 162946204
• LOTUS: LTS0146905
• wikiData: Q105360896