(4S,4aS,5S,8aS)-3,4a,5-trimethyl-4,5,6,7,8,9-hexahydrobenzo[f][1]benzofuran-4,8a-diol

Details

• Internal ID: 20e54194-43e5-4d67-b96d-be7aaed918aa
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (4S,4aS,5S,8aS)-3,4a,5-trimethyl-4,5,6,7,8,9-hexahydrobenzo[f][1]benzofuran-4,8a-diol
• SMILES (Canonical): CC1CCCC2(C1(C(C3=C(C2)OC=C3C)O)C)O
• SMILES (Isomeric): C[C@H]1CCC[C@]2([C@@]1([C@@H](C3=C(C2)OC=C3C)O)C)O
• InChI: InChI=1S/C15H22O3/c1-9-8-18-11-7-15(17)6-4-5-10(2)14(15,3)13(16)12(9)11/h8,10,13,16-17H,4-7H2,1-3H3/t10-,13+,14-,15-/m0/s1
• InChI Key: NEEFWFDZIRSXDP-PUPMMZHASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 53.60 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.73
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9910	99.10%
Caco-2	+	0.7553	75.53%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5053	50.53%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.9201	92.01%
OATP1B3 inhibitior	+	0.9382	93.82%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.5366	53.66%
P-glycoprotein inhibitior	-	0.9298	92.98%
P-glycoprotein substrate	-	0.8472	84.72%
CYP3A4 substrate	+	0.5587	55.87%
CYP2C9 substrate	-	0.5975	59.75%
CYP2D6 substrate	-	0.6821	68.21%
CYP3A4 inhibition	-	0.8051	80.51%
CYP2C9 inhibition	-	0.7401	74.01%
CYP2C19 inhibition	-	0.8121	81.21%
CYP2D6 inhibition	-	0.9370	93.70%
CYP1A2 inhibition	+	0.5424	54.24%
CYP2C8 inhibition	-	0.7287	72.87%
CYP inhibitory promiscuity	-	0.7726	77.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7800	78.00%
Carcinogenicity (trinary)	Non-required	0.5078	50.78%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.8278	82.78%
Skin irritation	-	0.5989	59.89%
Skin corrosion	-	0.9019	90.19%
Ames mutagenesis	-	0.6824	68.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.7381	73.81%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.6155	61.55%
skin sensitisation	-	0.8401	84.01%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8309	83.09%
Acute Oral Toxicity (c)	III	0.4879	48.79%
Estrogen receptor binding	+	0.6728	67.28%
Androgen receptor binding	+	0.5849	58.49%
Thyroid receptor binding	+	0.5542	55.42%
Glucocorticoid receptor binding	-	0.5085	50.85%
Aromatase binding	-	0.5796	57.96%
PPAR gamma	+	0.6419	64.19%
Honey bee toxicity	-	0.9192	91.92%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9650	96.50%

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	95.91%	91.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.14%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.67%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.07%	95.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.52%	93.04%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.78%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.57%	89.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	84.08%	86.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.81%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.71%	95.89%

Plants that contains it

• Ligularia kanaitzensis
• Ligularia subspicata
• Ligularia virgaurea
• Petasites japonicus

Cross-Links

• PubChem: 5317427
• NPASS: NPC58435
• LOTUS: LTS0238505
• wikiData: Q105177856