(4S,4aR,5S,8aR)-4-ethoxy-3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran

Details

• Internal ID: 375fa538-a681-4de6-a1ca-6ec4f3bd8016
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (4S,4aR,5S,8aR)-4-ethoxy-3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran
• SMILES (Canonical): CCOC1C2=C(CC3C1(C(CCC3)C)C)OC=C2C
• SMILES (Isomeric): CCO[C@@H]1C2=C(C[C@@H]3[C@]1([C@H](CCC3)C)C)OC=C2C
• InChI: InChI=1S/C17H26O2/c1-5-18-16-15-11(2)10-19-14(15)9-13-8-6-7-12(3)17(13,16)4/h10,12-13,16H,5-9H2,1-4H3/t12-,13+,16+,17+/m0/s1
• InChI Key: FFUWAMHKUYRIBZ-NSNWQYSKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₂
• Molecular Weight: 262.40 g/mol
• Exact Mass: 262.193280068 g/mol
• Topological Polar Surface Area (TPSA): 22.40 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.66
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• AKOS040734296

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9442	94.42%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5365	53.65%
OATP2B1 inhibitior	-	0.8518	85.18%
OATP1B1 inhibitior	+	0.9007	90.07%
OATP1B3 inhibitior	+	0.9571	95.71%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.8552	85.52%
P-glycoprotein inhibitior	-	0.8329	83.29%
P-glycoprotein substrate	-	0.8179	81.79%
CYP3A4 substrate	+	0.5721	57.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6571	65.71%
CYP3A4 inhibition	-	0.8845	88.45%
CYP2C9 inhibition	+	0.5179	51.79%
CYP2C19 inhibition	+	0.7430	74.30%
CYP2D6 inhibition	-	0.9194	91.94%
CYP1A2 inhibition	-	0.6429	64.29%
CYP2C8 inhibition	+	0.4810	48.10%
CYP inhibitory promiscuity	+	0.6193	61.93%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5869	58.69%
Eye corrosion	-	0.9829	98.29%
Eye irritation	-	0.8296	82.96%
Skin irritation	-	0.8228	82.28%
Skin corrosion	-	0.9718	97.18%
Ames mutagenesis	-	0.7136	71.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.3612	36.12%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.5535	55.35%
skin sensitisation	-	0.7957	79.57%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.7368	73.68%
Acute Oral Toxicity (c)	III	0.6766	67.66%
Estrogen receptor binding	+	0.7514	75.14%
Androgen receptor binding	+	0.5440	54.40%
Thyroid receptor binding	+	0.6406	64.06%
Glucocorticoid receptor binding	-	0.5414	54.14%
Aromatase binding	+	0.5228	52.28%
PPAR gamma	+	0.6712	67.12%
Honey bee toxicity	-	0.8490	84.90%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9824	98.24%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	94.38%	97.09%
CHEMBL2581	P07339	Cathepsin D	88.63%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.47%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.10%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.53%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.50%	92.94%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	83.24%	95.34%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.39%	94.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.18%	93.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.13%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	81.07%	90.17%

Plants that contains it

• Ligularia lamarum
• Ligularia subspicata
• Ligularia vellerea
• Ligularia virgaurea

Cross-Links

• PubChem: 12989626
• LOTUS: LTS0168793
• wikiData: Q104994692