[(3S,3aR,5aR,6S,7S,9aS,9bS)-6-hydroxy-3,5a-dimethyl-9-methylidene-2-oxo-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran-7-yl] acetate

Details

• Internal ID: c5fd68df-6d31-49ab-90c6-32539b986049
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3S,3aR,5aR,6S,7S,9aS,9bS)-6-hydroxy-3,5a-dimethyl-9-methylidene-2-oxo-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran-7-yl] acetate
• InChI: InChI=1S/C17H24O5/c1-8-7-12(21-10(3)18)15(19)17(4)6-5-11-9(2)16(20)22-14(11)13(8)17/h9,11-15,19H,1,5-7H2,2-4H3/t9-,11+,12-,13+,14-,15+,17+/m0/s1
• InChI Key: DUKXKHCYGRDGCW-LKJLYNOCSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₅
• Molecular Weight: 308.40 g/mol
• Exact Mass: 308.16237386 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.83
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9844	98.44%
Caco-2	-	0.6220	62.20%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7683	76.83%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.8956	89.56%
OATP1B3 inhibitior	-	0.3939	39.39%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5126	51.26%
BSEP inhibitior	-	0.9381	93.81%
P-glycoprotein inhibitior	-	0.7978	79.78%
P-glycoprotein substrate	-	0.7812	78.12%
CYP3A4 substrate	+	0.6830	68.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8571	85.71%
CYP3A4 inhibition	-	0.6008	60.08%
CYP2C9 inhibition	-	0.8508	85.08%
CYP2C19 inhibition	-	0.7827	78.27%
CYP2D6 inhibition	-	0.9295	92.95%
CYP1A2 inhibition	+	0.5406	54.06%
CYP2C8 inhibition	-	0.8735	87.35%
CYP inhibitory promiscuity	-	0.8719	87.19%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5759	57.59%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9502	95.02%
Skin irritation	+	0.5680	56.80%
Skin corrosion	-	0.8860	88.60%
Ames mutagenesis	-	0.6560	65.60%
Human Ether-a-go-go-Related Gene inhibition	-	0.8007	80.07%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.6315	63.15%
skin sensitisation	-	0.7777	77.77%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5856	58.56%
Acute Oral Toxicity (c)	III	0.5190	51.90%
Estrogen receptor binding	-	0.4786	47.86%
Androgen receptor binding	+	0.6100	61.00%
Thyroid receptor binding	-	0.5694	56.94%
Glucocorticoid receptor binding	+	0.6994	69.94%
Aromatase binding	-	0.7240	72.40%
PPAR gamma	-	0.7070	70.70%
Honey bee toxicity	-	0.7173	71.73%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5250	52.50%
Fish aquatic toxicity	+	0.9940	99.40%

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	95.67%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.04%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.77%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.09%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	88.27%	91.19%
CHEMBL2581	P07339	Cathepsin D	86.83%	98.95%
CHEMBL1902	P62942	FK506-binding protein 1A	86.04%	97.05%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.77%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.89%	89.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.72%	93.04%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.32%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.57%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.54%	95.89%

Plants that contains it

• Dolomiaea souliei

Cross-Links

• PubChem: 163020532
• LOTUS: LTS0245541
• wikiData: Q104989302