[(3R,4S,5S,6R)-2-[2-[(1aR,2R,4aR,7R,8aR)-2,7-dihydroxy-4a-methyl-8-methylidene-1a,3,4,5,6,7-hexahydronaphtho[1,8a-b]oxiren-2-yl]propan-2-yloxy]-6-methyl-3,5-bis[[(Z)-2-methylbut-2-enoyl]oxy]oxan-4-yl] 2-methylbutanoate

Details

• Internal ID: 10e63ead-794c-4df8-ab41-c9746a190fec
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(3R,4S,5S,6R)-2-[2-[(1aR,2R,4aR,7R,8aR)-2,7-dihydroxy-4a-methyl-8-methylidene-1a,3,4,5,6,7-hexahydronaphtho[1,8a-b]oxiren-2-yl]propan-2-yloxy]-6-methyl-3,5-bis[[(Z)-2-methylbut-2-enoyl]oxy]oxan-4-yl] 2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C(C(OC(C1OC(=O)C(=CC)C)OC(C)(C)C2(CCC3(CCC(C(=C)C34C2O4)O)C)O)C)OC(=O)C(=CC)C
• SMILES (Isomeric): CCC(C)C(=O)O[C@H]1[C@H]([C@H](OC([C@@H]1OC(=O)/C(=C\C)/C)OC(C)(C)[C@]2(CC[C@]3(CC[C@H](C(=C)[C@@]34[C@@H]2O4)O)C)O)C)OC(=O)/C(=C\C)/C
• InChI: InChI=1S/C36H54O11/c1-12-19(4)28(38)43-25-23(8)42-31(27(45-30(40)21(6)14-3)26(25)44-29(39)20(5)13-2)46-33(9,10)35(41)18-17-34(11)16-15-24(37)22(7)36(34)32(35)47-36/h12,14,20,23-27,31-32,37,41H,7,13,15-18H2,1-6,8-11H3/b19-12-,21-14-/t20?,23-,24-,25+,26+,27-,31?,32-,34-,35-,36-/m1/s1
• InChI Key: RHEWDGKENJHGQY-KFSDTLJXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₄O₁₁
• Molecular Weight: 662.80 g/mol
• Exact Mass: 662.36661253 g/mol
• Topological Polar Surface Area (TPSA): 150.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.62
• H-Bond Acceptor: 11
• H-Bond Donor: 2
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9768	97.68%
Caco-2	-	0.8290	82.90%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6957	69.57%
OATP2B1 inhibitior	-	0.8624	86.24%
OATP1B1 inhibitior	+	0.8174	81.74%
OATP1B3 inhibitior	+	0.8986	89.86%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9438	94.38%
P-glycoprotein inhibitior	+	0.7886	78.86%
P-glycoprotein substrate	+	0.6107	61.07%
CYP3A4 substrate	+	0.7043	70.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8939	89.39%
CYP3A4 inhibition	+	0.6456	64.56%
CYP2C9 inhibition	-	0.7328	73.28%
CYP2C19 inhibition	-	0.8080	80.80%
CYP2D6 inhibition	-	0.9360	93.60%
CYP1A2 inhibition	-	0.8485	84.85%
CYP2C8 inhibition	+	0.5357	53.57%
CYP inhibitory promiscuity	-	0.9388	93.88%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6688	66.88%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9088	90.88%
Skin irritation	-	0.5779	57.79%
Skin corrosion	-	0.9239	92.39%
Ames mutagenesis	-	0.5054	50.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.5131	51.31%
skin sensitisation	-	0.7832	78.32%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.6405	64.05%
Acute Oral Toxicity (c)	III	0.5028	50.28%
Estrogen receptor binding	+	0.7292	72.92%
Androgen receptor binding	+	0.7314	73.14%
Thyroid receptor binding	-	0.5051	50.51%
Glucocorticoid receptor binding	+	0.7666	76.66%
Aromatase binding	+	0.7451	74.51%
PPAR gamma	+	0.7115	71.15%
Honey bee toxicity	-	0.7351	73.51%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9944	99.44%

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	97.68%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.48%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.71%	97.25%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	95.21%	98.75%
CHEMBL2581	P07339	Cathepsin D	94.87%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.40%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.22%	96.61%
CHEMBL226	P30542	Adenosine A1 receptor	90.84%	95.93%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	90.70%	82.50%
CHEMBL340	P08684	Cytochrome P450 3A4	89.99%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.71%	89.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	88.86%	89.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	88.55%	100.00%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	88.00%	99.17%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.72%	96.47%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	86.12%	95.71%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	85.78%	97.47%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	85.65%	83.00%
CHEMBL4015	P41597	C-C chemokine receptor type 2	85.57%	98.57%
CHEMBL5028	O14672	ADAM10	85.37%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	85.24%	90.17%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.90%	96.77%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.84%	97.14%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.73%	91.03%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.32%	92.62%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.08%	96.90%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.49%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.47%	95.89%
CHEMBL2094135	Q96BI3	Gamma-secretase	83.13%	98.05%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.62%	89.34%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.59%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.44%	100.00%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	81.15%	97.31%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.07%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.61%	91.07%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.46%	93.56%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.16%	95.71%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	80.11%	92.78%

Plants that contains it

• Calendula arvensis

Cross-Links

• PubChem: 162816959
• LOTUS: LTS0262770
• wikiData: Q105236315