[(3R,3aS,5aR,6S,9aS,9bS)-3,5a-dimethyl-9-methylidene-2-oxo-3a,4,5,6,9a,9b-hexahydro-3H-benzo[g][1]benzofuran-6-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: a6a052cf-af31-4a07-ab0b-73ae943a453d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3R,3aS,5aR,6S,9aS,9bS)-3,5a-dimethyl-9-methylidene-2-oxo-3a,4,5,6,9a,9b-hexahydro-3H-benzo[g][1]benzofuran-6-yl] (Z)-2-methylbut-2-enoate
• InChI: InChI=1S/C20H26O4/c1-6-11(2)18(21)23-15-8-7-12(3)16-17-14(9-10-20(15,16)5)13(4)19(22)24-17/h6-8,13-17H,3,9-10H2,1-2,4-5H3/b11-6-/t13-,14+,15+,16-,17+,20+/m1/s1
• InChI Key: AOKVPXZYQSAPMF-GPJSXLMQSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.18310931 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.58
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9927	99.27%
Caco-2	+	0.6292	62.92%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5842	58.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8334	83.34%
OATP1B3 inhibitior	+	0.8066	80.66%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.4613	46.13%
P-glycoprotein inhibitior	-	0.6604	66.04%
P-glycoprotein substrate	-	0.7220	72.20%
CYP3A4 substrate	+	0.6833	68.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9139	91.39%
CYP3A4 inhibition	+	0.5614	56.14%
CYP2C9 inhibition	-	0.8467	84.67%
CYP2C19 inhibition	-	0.8213	82.13%
CYP2D6 inhibition	-	0.9253	92.53%
CYP1A2 inhibition	+	0.7620	76.20%
CYP2C8 inhibition	-	0.7724	77.24%
CYP inhibitory promiscuity	-	0.6092	60.92%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5052	50.52%
Eye corrosion	-	0.9836	98.36%
Eye irritation	-	0.9488	94.88%
Skin irritation	+	0.4949	49.49%
Skin corrosion	-	0.8557	85.57%
Ames mutagenesis	-	0.6980	69.80%
Human Ether-a-go-go-Related Gene inhibition	-	0.4240	42.40%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.7019	70.19%
skin sensitisation	-	0.6130	61.30%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.5751	57.51%
Acute Oral Toxicity (c)	III	0.7128	71.28%
Estrogen receptor binding	+	0.7502	75.02%
Androgen receptor binding	+	0.6819	68.19%
Thyroid receptor binding	-	0.5364	53.64%
Glucocorticoid receptor binding	+	0.5949	59.49%
Aromatase binding	-	0.4840	48.40%
PPAR gamma	-	0.5556	55.56%
Honey bee toxicity	-	0.6548	65.48%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9966	99.66%

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	98.65%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.06%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.02%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.68%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.52%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.60%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	86.97%	94.75%
CHEMBL340	P08684	Cytochrome P450 3A4	84.71%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.62%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.54%	86.33%
CHEMBL2581	P07339	Cathepsin D	84.51%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.27%	99.23%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	80.38%	92.95%

Plants that contains it

• Ferula oopoda

Cross-Links

• PubChem: 101306868
• LOTUS: LTS0023058
• wikiData: Q104249715