[(3aS,4S,5R,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-4-[(Z)-2-methylbut-2-enoyl]oxy-3-methylidene-2-oxo-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-5-yl] (2R,3R)-2,3-dimethyloxirane-2-carboxylate

Details

• Internal ID: 826e839a-8e6a-4ef5-8bee-538b0cfe9095
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3aS,4S,5R,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-4-[(Z)-2-methylbut-2-enoyl]oxy-3-methylidene-2-oxo-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-5-yl] (2R,3R)-2,3-dimethyloxirane-2-carboxylate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2C(C3C(=CCC(C3(C1OC(=O)C4(C(O4)C)C)C)O)C)OC(=O)C2=C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1[C@@H]2[C@H]([C@H]3C(=CC[C@H]([C@@]3([C@H]1OC(=O)[C@]4([C@H](O4)C)C)C)O)C)OC(=O)C2=C
• InChI: InChI=1S/C25H32O8/c1-8-11(2)21(27)31-19-16-13(4)22(28)30-18(16)17-12(3)9-10-15(26)24(17,6)20(19)32-23(29)25(7)14(5)33-25/h8-9,14-20,26H,4,10H2,1-3,5-7H3/b11-8-/t14-,15-,16+,17-,18-,19+,20+,24+,25-/m1/s1
• InChI Key: VBOVOGXZEUFLNR-HZQPAGJTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₈
• Molecular Weight: 460.50 g/mol
• Exact Mass: 460.20971797 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.40
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9890	98.90%
Caco-2	-	0.5572	55.72%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6267	62.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8465	84.65%
OATP1B3 inhibitior	+	0.8861	88.61%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7490	74.90%
P-glycoprotein inhibitior	+	0.7390	73.90%
P-glycoprotein substrate	+	0.5130	51.30%
CYP3A4 substrate	+	0.6657	66.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8793	87.93%
CYP3A4 inhibition	+	0.5520	55.20%
CYP2C9 inhibition	-	0.9379	93.79%
CYP2C19 inhibition	-	0.8940	89.40%
CYP2D6 inhibition	-	0.9361	93.61%
CYP1A2 inhibition	-	0.8828	88.28%
CYP2C8 inhibition	-	0.6221	62.21%
CYP inhibitory promiscuity	-	0.8841	88.41%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Danger	0.4174	41.74%
Eye corrosion	-	0.9812	98.12%
Eye irritation	-	0.9075	90.75%
Skin irritation	-	0.5894	58.94%
Skin corrosion	-	0.8942	89.42%
Ames mutagenesis	-	0.6296	62.96%
Human Ether-a-go-go-Related Gene inhibition	-	0.6708	67.08%
Micronuclear	-	0.5141	51.41%
Hepatotoxicity	+	0.7084	70.84%
skin sensitisation	-	0.6493	64.93%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6256	62.56%
Acute Oral Toxicity (c)	III	0.4128	41.28%
Estrogen receptor binding	+	0.7870	78.70%
Androgen receptor binding	+	0.6808	68.08%
Thyroid receptor binding	+	0.6258	62.58%
Glucocorticoid receptor binding	+	0.7201	72.01%
Aromatase binding	+	0.6663	66.63%
PPAR gamma	+	0.6986	69.86%
Honey bee toxicity	-	0.6203	62.03%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9655	96.55%

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	97.15%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.63%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	95.52%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.12%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.10%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.35%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.51%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.46%	93.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.69%	91.07%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.04%	97.25%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.41%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	85.62%	94.73%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.34%	93.03%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.34%	97.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.24%	94.45%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	84.57%	85.30%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.35%	97.21%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.97%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.44%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	80.46%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.28%	100.00%

Plants that contains it

• Calostephane divaricata

Cross-Links

• PubChem: 162916270
• LOTUS: LTS0069243
• wikiData: Q105283385