(3S,3aS,5aR,6S,8R,9bS)-6,8-dihydroxy-3,5a,9-trimethyl-3,3a,4,5,6,7,8,9b-octahydrobenzo[g][1]benzofuran-2-one

Details

• Internal ID: 387e78cb-cffd-4629-8da2-fb7e4cad476a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3S,3aS,5aR,6S,8R,9bS)-6,8-dihydroxy-3,5a,9-trimethyl-3,3a,4,5,6,7,8,9b-octahydrobenzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1C2CCC3(C(CC(C(=C3C2OC1=O)C)O)O)C
• SMILES (Isomeric): C[C@H]1[C@@H]2CC[C@]3([C@H](C[C@H](C(=C3[C@H]2OC1=O)C)O)O)C
• InChI: InChI=1S/C15H22O4/c1-7-9-4-5-15(3)11(17)6-10(16)8(2)12(15)13(9)19-14(7)18/h7,9-11,13,16-17H,4-6H2,1-3H3/t7-,9-,10+,11-,13-,15-/m0/s1
• InChI Key: FTWSMHMWRDSQDU-GYNAIRNASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.41
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 71241-93-5
• (3S,3aS,5aR,6S,8R,9bS)-3a,4,5,5a,6,7,8,9b-Octahydro-6,8-dihydroxy-3,5a,9-trimethylnaphtho[1,2-b]furan-2(3H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9877	98.77%
Caco-2	+	0.6809	68.09%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6955	69.55%
OATP2B1 inhibitior	-	0.8527	85.27%
OATP1B1 inhibitior	+	0.9186	91.86%
OATP1B3 inhibitior	+	0.9079	90.79%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5321	53.21%
BSEP inhibitior	-	0.9261	92.61%
P-glycoprotein inhibitior	-	0.8995	89.95%
P-glycoprotein substrate	-	0.7780	77.80%
CYP3A4 substrate	+	0.6070	60.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8383	83.83%
CYP3A4 inhibition	-	0.6676	66.76%
CYP2C9 inhibition	-	0.8985	89.85%
CYP2C19 inhibition	-	0.9175	91.75%
CYP2D6 inhibition	-	0.9535	95.35%
CYP1A2 inhibition	-	0.7177	71.77%
CYP2C8 inhibition	-	0.8859	88.59%
CYP inhibitory promiscuity	-	0.8846	88.46%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4752	47.52%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.8692	86.92%
Skin irritation	+	0.6700	67.00%
Skin corrosion	-	0.9138	91.38%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6010	60.10%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.6908	69.08%
skin sensitisation	-	0.8139	81.39%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.5990	59.90%
Acute Oral Toxicity (c)	I	0.4838	48.38%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	+	0.5973	59.73%
Thyroid receptor binding	+	0.5737	57.37%
Glucocorticoid receptor binding	-	0.5175	51.75%
Aromatase binding	-	0.7425	74.25%
PPAR gamma	-	0.6956	69.56%
Honey bee toxicity	-	0.7984	79.84%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9888	98.88%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.09%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.98%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.07%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.74%	91.11%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	86.50%	95.58%
CHEMBL1951	P21397	Monoamine oxidase A	85.00%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.35%	96.09%

Plants that contains it

• Artemisia szowitziana

Cross-Links

• PubChem: 13944249
• LOTUS: LTS0196617
• wikiData: Q105001429