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

Details

• Internal ID: 33480ee7-7189-4996-b038-48d141af6b78
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (4aS,8R,8aR,9aS)-8-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)CCC(C3(CC2OC1=O)C)O
• SMILES (Isomeric): CC1=C2C[C@H]3C(=C)CC[C@H]([C@@]3(C[C@@H]2OC1=O)C)O
• InChI: InChI=1S/C15H20O3/c1-8-4-5-13(16)15(3)7-12-10(6-11(8)15)9(2)14(17)18-12/h11-13,16H,1,4-7H2,2-3H3/t11-,12-,13+,15+/m0/s1
• InChI Key: UCBTXCZDWDKENW-RMRHIDDWSA-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: 1.50
• 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	+	0.9968	99.68%
Caco-2	+	0.7446	74.46%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7508	75.08%
OATP2B1 inhibitior	-	0.8548	85.48%
OATP1B1 inhibitior	+	0.9013	90.13%
OATP1B3 inhibitior	+	0.9367	93.67%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.6401	64.01%
BSEP inhibitior	-	0.7686	76.86%
P-glycoprotein inhibitior	-	0.8893	88.93%
P-glycoprotein substrate	-	0.8534	85.34%
CYP3A4 substrate	+	0.6453	64.53%
CYP2C9 substrate	-	0.7907	79.07%
CYP2D6 substrate	-	0.8724	87.24%
CYP3A4 inhibition	-	0.5092	50.92%
CYP2C9 inhibition	-	0.9116	91.16%
CYP2C19 inhibition	-	0.7134	71.34%
CYP2D6 inhibition	-	0.9372	93.72%
CYP1A2 inhibition	-	0.6548	65.48%
CYP2C8 inhibition	-	0.8548	85.48%
CYP inhibitory promiscuity	-	0.8995	89.95%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4993	49.93%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.8634	86.34%
Skin irritation	+	0.5863	58.63%
Skin corrosion	-	0.9113	91.13%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4352	43.52%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.6908	69.08%
skin sensitisation	-	0.6976	69.76%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.4746	47.46%
Acute Oral Toxicity (c)	III	0.4980	49.80%
Estrogen receptor binding	+	0.6183	61.83%
Androgen receptor binding	+	0.5675	56.75%
Thyroid receptor binding	+	0.5603	56.03%
Glucocorticoid receptor binding	+	0.6848	68.48%
Aromatase binding	-	0.5697	56.97%
PPAR gamma	+	0.5302	53.02%
Honey bee toxicity	-	0.8945	89.45%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9953	99.53%

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	92.94%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.13%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.95%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.63%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.57%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.07%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.17%	99.23%
CHEMBL1871	P10275	Androgen Receptor	83.26%	96.43%
CHEMBL2581	P07339	Cathepsin D	83.23%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.43%	95.89%

Plants that contains it

• Actinidia chinensis var. deliciosa
• Lepidium apetalum
• Licaria triandra

Cross-Links

• PubChem: 21635672
• NPASS: NPC103438
• LOTUS: LTS0251773
• wikiData: Q105269798