(5-Hydroxy-3,4a,5-trimethyl-4,6,7,9-tetrahydrobenzo[f][1]benzofuran-4-yl) 3-methylbutanoate

Details

• Internal ID: 3fb95fe8-2217-4136-9384-e8c144d77c01
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (5-hydroxy-3,4a,5-trimethyl-4,6,7,9-tetrahydrobenzo[f][1]benzofuran-4-yl) 3-methylbutanoate
• SMILES (Canonical): CC1=COC2=C1C(C3(C(=CCCC3(C)O)C2)C)OC(=O)CC(C)C
• SMILES (Isomeric): CC1=COC2=C1C(C3(C(=CCCC3(C)O)C2)C)OC(=O)CC(C)C
• InChI: InChI=1S/C20H28O4/c1-12(2)9-16(21)24-18-17-13(3)11-23-15(17)10-14-7-6-8-19(4,22)20(14,18)5/h7,11-12,18,22H,6,8-10H2,1-5H3
• InChI Key: CSMYUTLLPHMJQJ-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.19875937 g/mol
• Topological Polar Surface Area (TPSA): 59.70 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 4.25
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9966	99.66%
Caco-2	+	0.8132	81.32%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8054	80.54%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.8833	88.33%
OATP1B3 inhibitior	-	0.2853	28.53%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.6878	68.78%
P-glycoprotein inhibitior	-	0.6908	69.08%
P-glycoprotein substrate	-	0.7333	73.33%
CYP3A4 substrate	+	0.6380	63.80%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.8430	84.30%
CYP3A4 inhibition	+	0.6398	63.98%
CYP2C9 inhibition	+	0.5065	50.65%
CYP2C19 inhibition	+	0.5202	52.02%
CYP2D6 inhibition	-	0.8982	89.82%
CYP1A2 inhibition	+	0.6363	63.63%
CYP2C8 inhibition	-	0.5583	55.83%
CYP inhibitory promiscuity	-	0.5771	57.71%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5916	59.16%
Eye corrosion	-	0.9935	99.35%
Eye irritation	-	0.9133	91.33%
Skin irritation	-	0.5457	54.57%
Skin corrosion	-	0.9456	94.56%
Ames mutagenesis	-	0.5082	50.82%
Human Ether-a-go-go-Related Gene inhibition	+	0.6888	68.88%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.5755	57.55%
skin sensitisation	-	0.8153	81.53%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8468	84.68%
Acute Oral Toxicity (c)	I	0.4693	46.93%
Estrogen receptor binding	-	0.5607	56.07%
Androgen receptor binding	+	0.6524	65.24%
Thyroid receptor binding	+	0.6283	62.83%
Glucocorticoid receptor binding	+	0.7037	70.37%
Aromatase binding	+	0.6007	60.07%
PPAR gamma	+	0.6696	66.96%
Honey bee toxicity	-	0.8305	83.05%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.04%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.00%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.89%	97.25%
CHEMBL2581	P07339	Cathepsin D	90.55%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.73%	95.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.36%	96.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.57%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.56%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.10%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	81.67%	90.17%
CHEMBL5028	O14672	ADAM10	81.20%	97.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.47%	96.47%

Plants that contains it

• Euryops jacksonii

Cross-Links

• PubChem: 14890337
• LOTUS: LTS0186984
• wikiData: Q104969448