methyl (3S)-3-[(3S,3aS,5aR,6S,7S,9R,9aR)-9-acetyloxy-3-[(3S,5R,6S)-5,6-dihydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-3a,6,9a-trimethyl-7-prop-1-en-2-yl-2,3,4,5,5a,7,8,9-octahydrocyclopenta[a]naphthalen-6-yl]-3-acetyloxypropanoate

Details

• Internal ID: 1c1fd9d7-7cc4-4675-a51c-ce6d6dba1d26
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: methyl (3S)-3-[(3S,3aS,5aR,6S,7S,9R,9aR)-9-acetyloxy-3-[(3S,5R,6S)-5,6-dihydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-3a,6,9a-trimethyl-7-prop-1-en-2-yl-2,3,4,5,5a,7,8,9-octahydrocyclopenta[a]naphthalen-6-yl]-3-acetyloxypropanoate
• SMILES (Canonical): CC(=C)C1CC(C2(C(C1(C)C(CC(=O)OC)OC(=O)C)CCC3(C2=CCC3C4CC(C(OC4)(C(C)(C)O)O)O)C)C)OC(=O)C
• SMILES (Isomeric): CC(=C)[C@@H]1C[C@H]([C@@]2([C@@H]([C@@]1(C)[C@H](CC(=O)OC)OC(=O)C)CC[C@@]3(C2=CC[C@H]3[C@@H]4C[C@H]([C@](OC4)(C(C)(C)O)O)O)C)C)OC(=O)C
• InChI: InChI=1S/C35H54O10/c1-19(2)24-16-28(44-20(3)36)34(9)25-12-11-23(22-15-27(38)35(41,43-18-22)31(5,6)40)32(25,7)14-13-26(34)33(24,8)29(45-21(4)37)17-30(39)42-10/h12,22-24,26-29,38,40-41H,1,11,13-18H2,2-10H3/t22-,23+,24+,26-,27-,28-,29+,32+,33+,34+,35+/m1/s1
• InChI Key: QBABZGKLNBXUTN-ANXZYFOCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₄O₁₀
• Molecular Weight: 634.80 g/mol
• Exact Mass: 634.37169792 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.24
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9173	91.73%
Caco-2	-	0.8115	81.15%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8523	85.23%
OATP2B1 inhibitior	-	0.7225	72.25%
OATP1B1 inhibitior	+	0.8520	85.20%
OATP1B3 inhibitior	+	0.8968	89.68%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8542	85.42%
BSEP inhibitior	+	0.8171	81.71%
P-glycoprotein inhibitior	+	0.7459	74.59%
P-glycoprotein substrate	+	0.6406	64.06%
CYP3A4 substrate	+	0.7500	75.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8714	87.14%
CYP3A4 inhibition	-	0.7580	75.80%
CYP2C9 inhibition	-	0.7544	75.44%
CYP2C19 inhibition	-	0.8477	84.77%
CYP2D6 inhibition	-	0.9394	93.94%
CYP1A2 inhibition	-	0.8564	85.64%
CYP2C8 inhibition	+	0.7209	72.09%
CYP inhibitory promiscuity	-	0.9254	92.54%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6901	69.01%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9146	91.46%
Skin irritation	-	0.5439	54.39%
Skin corrosion	-	0.9371	93.71%
Ames mutagenesis	-	0.6528	65.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.4105	41.05%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8916	89.16%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6413	64.13%
Acute Oral Toxicity (c)	I	0.5477	54.77%
Estrogen receptor binding	+	0.7267	72.67%
Androgen receptor binding	+	0.7303	73.03%
Thyroid receptor binding	+	0.5372	53.72%
Glucocorticoid receptor binding	+	0.7532	75.32%
Aromatase binding	+	0.6886	68.86%
PPAR gamma	+	0.6731	67.31%
Honey bee toxicity	-	0.6576	65.76%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9893	98.93%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.53%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.38%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.88%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.35%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.12%	85.14%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	94.98%	97.21%
CHEMBL4040	P28482	MAP kinase ERK2	94.86%	83.82%
CHEMBL5028	O14672	ADAM10	90.35%	97.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.30%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	89.91%	91.19%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.67%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.97%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.49%	91.07%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.25%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.40%	96.77%
CHEMBL2581	P07339	Cathepsin D	85.90%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.68%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.48%	89.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.41%	97.28%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.43%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.18%	93.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.95%	97.14%
CHEMBL1871	P10275	Androgen Receptor	82.64%	96.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.10%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.89%	94.33%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	81.83%	94.97%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.76%	95.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.23%	95.89%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.15%	96.90%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.02%	95.56%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.00%	97.33%

Plants that contains it

• Trichilia elegans

Cross-Links

• PubChem: 163051427
• LOTUS: LTS0195678
• wikiData: Q105217699