(4aS,8aS,9S,9aR)-9-hydroxy-3,8a-dimethyl-5-methylidene-4a,6,7,8,9,9a-hexahydro-4H-benzo[f][1]benzofuran-2-one

Details

• Internal ID: 76eed3e4-acba-4cee-90c7-1d65f01e6822
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (4aS,8aS,9S,9aR)-9-hydroxy-3,8a-dimethyl-5-methylidene-4a,6,7,8,9,9a-hexahydro-4H-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1=C2CC3C(=C)CCCC3(C(C2OC1=O)O)C
• SMILES (Isomeric): CC1=C2C[C@H]3C(=C)CCC[C@@]3([C@@H]([C@@H]2OC1=O)O)C
• InChI: InChI=1S/C15H20O3/c1-8-5-4-6-15(3)11(8)7-10-9(2)14(17)18-12(10)13(15)16/h11-13,16H,1,4-7H2,2-3H3/t11-,12+,13+,15-/m0/s1
• InChI Key: RVRGUBAZBPVMKB-JLNYLFASSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.36
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9950	99.50%
Caco-2	+	0.7542	75.42%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7163	71.63%
OATP2B1 inhibitior	-	0.8530	85.30%
OATP1B1 inhibitior	+	0.8597	85.97%
OATP1B3 inhibitior	+	0.9038	90.38%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	-	0.8628	86.28%
P-glycoprotein inhibitior	-	0.8536	85.36%
P-glycoprotein substrate	-	0.9239	92.39%
CYP3A4 substrate	+	0.5869	58.69%
CYP2C9 substrate	-	0.7907	79.07%
CYP2D6 substrate	-	0.8724	87.24%
CYP3A4 inhibition	-	0.5249	52.49%
CYP2C9 inhibition	-	0.8217	82.17%
CYP2C19 inhibition	-	0.6532	65.32%
CYP2D6 inhibition	-	0.9031	90.31%
CYP1A2 inhibition	+	0.6620	66.20%
CYP2C8 inhibition	-	0.9211	92.11%
CYP inhibitory promiscuity	-	0.7841	78.41%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4996	49.96%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.8233	82.33%
Skin irritation	+	0.5240	52.40%
Skin corrosion	-	0.9148	91.48%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6239	62.39%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.6033	60.33%
skin sensitisation	-	0.6889	68.89%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.7142	71.42%
Acute Oral Toxicity (c)	III	0.4770	47.70%
Estrogen receptor binding	+	0.5273	52.73%
Androgen receptor binding	+	0.5560	55.60%
Thyroid receptor binding	-	0.5091	50.91%
Glucocorticoid receptor binding	+	0.6651	66.51%
Aromatase binding	-	0.7278	72.78%
PPAR gamma	-	0.5931	59.31%
Honey bee toxicity	-	0.8751	87.51%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	91.58%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.33%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.74%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.10%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.56%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.92%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.93%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.75%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	81.61%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.58%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.33%	94.00%
CHEMBL2581	P07339	Cathepsin D	80.69%	98.95%

Plants that contains it

• Chloranthus multistachys
• Hedyosmum orientale

Cross-Links

• PubChem: 25033525
• LOTUS: LTS0038361
• wikiData: Q105246264