(3aR)-2,10beta,11,11-Tetramethyl-3-oxo-9alpha,10abeta-dihydroxy-5-(linoleoyloxy)methyl-8beta-(acetyloxy)-7,8-methano-3,3abeta,4,6aalpha,7beta,8,9,10,10a,10bbeta-decahydrobenzo[e]azulene

Details

• Internal ID: c8ea5ccf-03da-4314-8b0d-02f0472908d9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Tigliane and ingenane diterpenoids
• IUPAC Name: [(1R,2R,6R,10S,11R,13S,14R,15R)-13-acetyloxy-1,14-dihydroxy-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)C4C1)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@@H]4C1)C)O)C)O)OC(=O)C
• InChI: InChI=1S/C40H60O7/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-34(42)46-26-30-24-31-32(23-27(2)35(31)43)39(45)28(3)37(44)40(47-29(4)41)36(33(39)25-30)38(40,5)6/h11-12,14-15,23,25,28,31-33,36-37,44-45H,7-10,13,16-22,24,26H2,1-6H3/b12-11-,15-14-/t28-,31-,32-,33+,36-,37-,39+,40-/m1/s1
• InChI Key: YCILLHFFVLLMRC-MIAPNZHBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₀O₇
• Molecular Weight: 652.90 g/mol
• Exact Mass: 652.43390425 g/mol
• Topological Polar Surface Area (TPSA): 110.00 Ų
• XlogP: 7.90
• Atomic LogP (AlogP): 7.75
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 17

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9727	97.27%
Caco-2	-	0.8228	82.28%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8000	80.00%
OATP2B1 inhibitior	-	0.8574	85.74%
OATP1B1 inhibitior	+	0.7441	74.41%
OATP1B3 inhibitior	+	0.9502	95.02%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6343	63.43%
BSEP inhibitior	+	0.9859	98.59%
P-glycoprotein inhibitior	+	0.7699	76.99%
P-glycoprotein substrate	+	0.6457	64.57%
CYP3A4 substrate	+	0.7011	70.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9170	91.70%
CYP3A4 inhibition	-	0.8641	86.41%
CYP2C9 inhibition	+	0.6673	66.73%
CYP2C19 inhibition	-	0.8719	87.19%
CYP2D6 inhibition	-	0.9093	90.93%
CYP1A2 inhibition	-	0.8236	82.36%
CYP2C8 inhibition	+	0.6681	66.81%
CYP inhibitory promiscuity	-	0.7582	75.82%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6533	65.33%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9186	91.86%
Skin irritation	-	0.5127	51.27%
Skin corrosion	-	0.9551	95.51%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6915	69.15%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8213	82.13%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7215	72.15%
Acute Oral Toxicity (c)	III	0.5018	50.18%
Estrogen receptor binding	+	0.8120	81.20%
Androgen receptor binding	+	0.7342	73.42%
Thyroid receptor binding	-	0.5294	52.94%
Glucocorticoid receptor binding	+	0.7364	73.64%
Aromatase binding	+	0.5851	58.51%
PPAR gamma	+	0.6522	65.22%
Honey bee toxicity	-	0.8073	80.73%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.8300	83.00%
Fish aquatic toxicity	+	0.9955	99.55%

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	97.98%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.64%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	97.59%	97.79%
CHEMBL299	P17252	Protein kinase C alpha	97.20%	98.03%
CHEMBL3060	Q9Y345	Glycine transporter 2	97.04%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.91%	91.11%
CHEMBL3045	P05771	Protein kinase C beta	94.07%	97.63%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.74%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.95%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.88%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.57%	89.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	89.41%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	87.95%	90.17%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	87.61%	85.94%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.57%	96.95%
CHEMBL5255	O00206	Toll-like receptor 4	87.05%	92.50%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.29%	97.21%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.70%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.49%	95.56%
CHEMBL5103	Q969S8	Histone deacetylase 10	85.30%	90.08%
CHEMBL1937	Q92769	Histone deacetylase 2	85.12%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.27%	97.09%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	84.05%	92.08%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.90%	94.33%
CHEMBL1902	P62942	FK506-binding protein 1A	83.67%	97.05%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.21%	100.00%
CHEMBL2664	P23526	Adenosylhomocysteinase	83.07%	86.67%
CHEMBL340	P08684	Cytochrome P450 3A4	82.29%	91.19%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.78%	93.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.36%	100.00%

Plants that contains it

• Croton tiglium

Cross-Links

• PubChem: 73350379
• NPASS: NPC146280
• ChEMBL: CHEMBL2375792
• LOTUS: LTS0001166
• wikiData: Q105346283