methyl (3S)-3-[(3S,3aS,5aR,6S,7S,9R,9aR)-3-[(3S,5R,6S)-5,6-dihydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-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: 09d6f319-0daa-4bb7-a5e9-fe18cafb6e0c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: methyl (3S)-3-[(3S,3aS,5aR,6S,7S,9R,9aR)-3-[(3S,5R,6S)-5,6-dihydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-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)O
• 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)O
• InChI: InChI=1S/C33H52O9/c1-18(2)22-15-25(35)32(8)23-11-10-21(20-14-26(36)33(39,41-17-20)29(4,5)38)30(23,6)13-12-24(32)31(22,7)27(42-19(3)34)16-28(37)40-9/h11,20-22,24-27,35-36,38-39H,1,10,12-17H2,2-9H3/t20-,21+,22+,24-,25-,26-,27+,30+,31+,32+,33+/m1/s1
• InChI Key: DVQXYBYHXZHGRQ-KAYXFQKTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₂O₉
• Molecular Weight: 592.80 g/mol
• Exact Mass: 592.36113323 g/mol
• Topological Polar Surface Area (TPSA): 143.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.67
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 7

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	-	0.7866	78.66%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8523	85.23%
OATP2B1 inhibitior	-	0.7157	71.57%
OATP1B1 inhibitior	+	0.8709	87.09%
OATP1B3 inhibitior	+	0.8968	89.68%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8542	85.42%
BSEP inhibitior	+	0.8032	80.32%
P-glycoprotein inhibitior	+	0.6921	69.21%
P-glycoprotein substrate	+	0.6259	62.59%
CYP3A4 substrate	+	0.7422	74.22%
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	+	0.6835	68.35%
CYP inhibitory promiscuity	-	0.9254	92.54%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6901	69.01%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9193	91.93%
Skin irritation	-	0.5439	54.39%
Skin corrosion	-	0.9371	93.71%
Ames mutagenesis	-	0.6628	66.28%
Human Ether-a-go-go-Related Gene inhibition	+	0.7057	70.57%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8916	89.16%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6196	61.96%
Acute Oral Toxicity (c)	I	0.5477	54.77%
Estrogen receptor binding	+	0.7026	70.26%
Androgen receptor binding	+	0.7440	74.40%
Thyroid receptor binding	+	0.5365	53.65%
Glucocorticoid receptor binding	+	0.7168	71.68%
Aromatase binding	+	0.6851	68.51%
PPAR gamma	+	0.6463	64.63%
Honey bee toxicity	-	0.6868	68.68%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
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	98.66%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.61%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.41%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.01%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.11%	85.14%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	93.51%	97.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.68%	96.95%
CHEMBL5028	O14672	ADAM10	90.89%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	90.84%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.44%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.75%	97.09%
CHEMBL2581	P07339	Cathepsin D	87.66%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.34%	82.69%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.20%	96.77%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.96%	93.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.27%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.23%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.09%	89.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.83%	95.71%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.31%	96.61%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.91%	97.28%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.65%	96.90%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.10%	94.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.08%	97.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.36%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.04%	95.89%
CHEMBL1871	P10275	Androgen Receptor	80.75%	96.43%
CHEMBL3401	O75469	Pregnane X receptor	80.01%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.00%	95.89%

Plants that contains it

• Aphanamixis polystachya
• Capsicum annuum

Cross-Links

• PubChem: 71531902
• LOTUS: LTS0240146
• wikiData: Q104973897