[(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] hexadecanoate

Details

• Internal ID: 54589f54-c400-4dbb-8cec-4556cfa30355
• 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] hexadecanoate
• SMILES (Canonical): CCCCCCCCCCCCCCCC(=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): CCCCCCCCCCCCCCCC(=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/C38H60O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-31(41)45-34-26(3)37(44)29(32-35(5,6)38(32,34)46-27(4)40)22-28(24-39)23-36(43)30(37)21-25(2)33(36)42/h21-22,26,29-30,32,34,39,43-44H,7-20,23-24H2,1-6H3/t26-,29+,30-,32-,34-,36-,37-,38-/m1/s1
• InChI Key: DPSHFDIHUAPDMN-MNAUBHHSSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₆₀O₈
• Molecular Weight: 644.90 g/mol
• Exact Mass: 644.42881887 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 7.60
• Atomic LogP (AlogP): 6.53
• 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	+	0.9816	98.16%
Caco-2	-	0.8123	81.23%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7776	77.76%
OATP2B1 inhibitior	-	0.7185	71.85%
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	+	0.8924	89.24%
P-glycoprotein inhibitior	+	0.7583	75.83%
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	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7029	70.29%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9067	90.67%
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	-	0.3706	37.06%
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	+	0.7376	73.76%
Androgen receptor binding	+	0.7165	71.65%
Thyroid receptor binding	-	0.5726	57.26%
Glucocorticoid receptor binding	+	0.6608	66.08%
Aromatase binding	+	0.6458	64.58%
PPAR gamma	+	0.6046	60.46%
Honey bee toxicity	-	0.8428	84.28%
Biodegradation	-	0.7000	70.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	10 nM	Potency	via Super-PRED
CHEMBL299	P17252	Protein kinase C alpha	2.5 nM	Ki	via Super-PRED
CHEMBL3045	P05771	Protein kinase C beta	1.8 nM	Ki	via Super-PRED
CHEMBL2996	Q05655	Protein kinase C delta	0.8 nM	Ki	via Super-PRED
CHEMBL3582	Q02156	Protein kinase C epsilon	0.45 nM	Ki	via Super-PRED
CHEMBL2938	P05129	Protein kinase C gamma	4.9 nM	Ki	via Super-PRED
CHEMBL3638	Q8IV61	RAS guanyl releasing protein 3	82 nM	EC50	via Super-PRED
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

• Croton tiglium
• Triadica sebifera
• Vernicia fordii

Cross-Links

• PubChem: 119080
• NPASS: NPC5991
• LOTUS: LTS0206972
• wikiData: Q104986689