5-[2-(Furan-3-YL)ethyl]-8-hydroxy-5,6,8A-trimethyl-3,4,4A,6,7,8-hexahydronaphthalene-1-carboxylic acid

Details

• Internal ID: 2bd223ed-7340-4578-8205-dbd054a5ffa4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: 5-[2-(furan-3-yl)ethyl]-8-hydroxy-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid
• SMILES (Canonical): CC1CC(C2(C(C1(C)CCC3=COC=C3)CCC=C2C(=O)O)C)O
• SMILES (Isomeric): CC1CC(C2(C(C1(C)CCC3=COC=C3)CCC=C2C(=O)O)C)O
• InChI: InChI=1S/C20H28O4/c1-13-11-17(21)20(3)15(18(22)23)5-4-6-16(20)19(13,2)9-7-14-8-10-24-12-14/h5,8,10,12-13,16-17,21H,4,6-7,9,11H2,1-3H3,(H,22,23)
• InChI Key: XWKYXEIGWQYOCY-UHFFFAOYSA-N
• Popularity: 3 references 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): 70.70 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.05
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• CHEBI:181045
• NCGC00385270-01
• 5-[2-(uran-3-yl)ethyl]-8-hydroxy-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9911	99.11%
Caco-2	+	0.7481	74.81%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6485	64.85%
OATP2B1 inhibitior	-	0.8665	86.65%
OATP1B1 inhibitior	+	0.7310	73.10%
OATP1B3 inhibitior	+	0.9492	94.92%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.8148	81.48%
P-glycoprotein substrate	-	0.5990	59.90%
CYP3A4 substrate	+	0.6053	60.53%
CYP2C9 substrate	-	0.7953	79.53%
CYP2D6 substrate	-	0.8881	88.81%
CYP3A4 inhibition	+	0.7761	77.61%
CYP2C9 inhibition	-	0.9142	91.42%
CYP2C19 inhibition	-	0.8227	82.27%
CYP2D6 inhibition	-	0.9049	90.49%
CYP1A2 inhibition	-	0.6319	63.19%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.6783	67.83%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5053	50.53%
Eye corrosion	-	0.9964	99.64%
Eye irritation	-	0.9686	96.86%
Skin irritation	+	0.6491	64.91%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6612	66.12%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.5652	56.52%
skin sensitisation	-	0.7932	79.32%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.6151	61.51%
Acute Oral Toxicity (c)	III	0.5235	52.35%
Estrogen receptor binding	+	0.7341	73.41%
Androgen receptor binding	+	0.5762	57.62%
Thyroid receptor binding	+	0.6350	63.50%
Glucocorticoid receptor binding	+	0.6960	69.60%
Aromatase binding	+	0.7655	76.55%
PPAR gamma	+	0.5345	53.45%
Honey bee toxicity	-	0.8703	87.03%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9963	99.63%

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	95.88%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.96%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.23%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.12%	91.11%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	90.71%	93.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.00%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.55%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.62%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	83.85%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.41%	89.00%
CHEMBL5028	O14672	ADAM10	80.35%	97.50%

Plants that contains it

• Duranta erecta

Cross-Links

• PubChem: 45359865
• LOTUS: LTS0165402
• wikiData: Q104667545