(4aR,5R,6R,8aR)-6-hydroxy-3,4a,5-trimethyl-4,5,6,7,8,8a-hexahydrobenzo[f][1]benzofuran-9-one

Details

• Internal ID: 989ffc51-a901-4191-9bfb-a48dc34e5cdd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (4aR,5R,6R,8aR)-6-hydroxy-3,4a,5-trimethyl-4,5,6,7,8,8a-hexahydrobenzo[f][1]benzofuran-9-one
• SMILES (Canonical): CC1C(CCC2C1(CC3=C(C2=O)OC=C3C)C)O
• SMILES (Isomeric): C[C@H]1[C@@H](CC[C@@H]2[C@@]1(CC3=C(C2=O)OC=C3C)C)O
• InChI: InChI=1S/C15H20O3/c1-8-7-18-14-10(8)6-15(3)9(2)12(16)5-4-11(15)13(14)17/h7,9,11-12,16H,4-6H2,1-3H3/t9-,11-,12+,15+/m0/s1
• InChI Key: LWPOKQLTDYARRB-APAOZMKASA-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): 50.40 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.74
• 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	+	0.9974	99.74%
Caco-2	+	0.7251	72.51%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7636	76.36%
OATP2B1 inhibitior	-	0.8495	84.95%
OATP1B1 inhibitior	+	0.8993	89.93%
OATP1B3 inhibitior	+	0.9307	93.07%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	-	0.7844	78.44%
P-glycoprotein inhibitior	-	0.9380	93.80%
P-glycoprotein substrate	-	0.8847	88.47%
CYP3A4 substrate	+	0.6013	60.13%
CYP2C9 substrate	-	0.7735	77.35%
CYP2D6 substrate	-	0.8054	80.54%
CYP3A4 inhibition	-	0.6184	61.84%
CYP2C9 inhibition	-	0.7451	74.51%
CYP2C19 inhibition	-	0.6352	63.52%
CYP2D6 inhibition	-	0.9433	94.33%
CYP1A2 inhibition	+	0.5562	55.62%
CYP2C8 inhibition	-	0.9028	90.28%
CYP inhibitory promiscuity	-	0.9031	90.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.5328	53.28%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.9634	96.34%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9036	90.36%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6236	62.36%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	+	0.6302	63.02%
skin sensitisation	-	0.8509	85.09%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.6654	66.54%
Acute Oral Toxicity (c)	III	0.4874	48.74%
Estrogen receptor binding	-	0.5663	56.63%
Androgen receptor binding	+	0.5906	59.06%
Thyroid receptor binding	-	0.5629	56.29%
Glucocorticoid receptor binding	+	0.5406	54.06%
Aromatase binding	-	0.6343	63.43%
PPAR gamma	+	0.5873	58.73%
Honey bee toxicity	-	0.9321	93.21%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9747	97.47%

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	95.69%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.63%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.78%	97.09%
CHEMBL2581	P07339	Cathepsin D	88.38%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.27%	89.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.34%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.37%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.30%	99.23%

Plants that contains it

• Euryops floribundus

Cross-Links

• PubChem: 101289748
• LOTUS: LTS0196960
• wikiData: Q105158493