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

Details

• Internal ID: 75cf147b-ef97-4bbf-9b10-66c0943753c4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3aR,4S,5aR,6R,9aS,9bR)-6-hydroxy-5a,9-dimethyl-3-methylidene-2-oxo-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate
• SMILES (Canonical): CC1C(O1)(C)C(=O)OC2CC3(C(CC=C(C3C4C2C(=C)C(=O)O4)C)O)C
• SMILES (Isomeric): C[C@H]1[C@@](O1)(C)C(=O)O[C@H]2C[C@]3([C@@H](CC=C([C@@H]3[C@@H]4[C@@H]2C(=C)C(=O)O4)C)O)C
• InChI: InChI=1S/C20H26O6/c1-9-6-7-13(21)19(4)8-12(24-18(23)20(5)11(3)26-20)14-10(2)17(22)25-16(14)15(9)19/h6,11-16,21H,2,7-8H2,1,3-5H3/t11-,12-,13+,14+,15+,16-,19-,20-/m0/s1
• InChI Key: NWAGJEHYRXNHPW-JWKHKKNQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.40 g/mol
• Exact Mass: 362.17293854 g/mol
• Topological Polar Surface Area (TPSA): 85.40 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.91
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9906	99.06%
Caco-2	+	0.6081	60.81%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6385	63.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8985	89.85%
OATP1B3 inhibitior	+	0.8501	85.01%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9243	92.43%
P-glycoprotein inhibitior	-	0.6038	60.38%
P-glycoprotein substrate	-	0.6907	69.07%
CYP3A4 substrate	+	0.6817	68.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8556	85.56%
CYP3A4 inhibition	+	0.7583	75.83%
CYP2C9 inhibition	-	0.8543	85.43%
CYP2C19 inhibition	-	0.8705	87.05%
CYP2D6 inhibition	-	0.9526	95.26%
CYP1A2 inhibition	-	0.8200	82.00%
CYP2C8 inhibition	-	0.6549	65.49%
CYP inhibitory promiscuity	-	0.9237	92.37%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4503	45.03%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9425	94.25%
Skin irritation	-	0.5469	54.69%
Skin corrosion	-	0.9019	90.19%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3664	36.64%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	+	0.7316	73.16%
skin sensitisation	-	0.7367	73.67%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.6179	61.79%
Acute Oral Toxicity (c)	III	0.3667	36.67%
Estrogen receptor binding	+	0.7526	75.26%
Androgen receptor binding	+	0.6891	68.91%
Thyroid receptor binding	+	0.6551	65.51%
Glucocorticoid receptor binding	+	0.6824	68.24%
Aromatase binding	+	0.5310	53.10%
PPAR gamma	+	0.5471	54.71%
Honey bee toxicity	-	0.6521	65.21%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5850	58.50%
Fish aquatic toxicity	+	0.9932	99.32%

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	93.32%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.13%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.41%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.01%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	88.17%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.06%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.57%	94.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.64%	91.07%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.80%	97.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.73%	93.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.59%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.56%	89.00%
CHEMBL4208	P20618	Proteasome component C5	82.23%	90.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.21%	96.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.20%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.27%	100.00%
CHEMBL1871	P10275	Androgen Receptor	81.01%	96.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.07%	95.89%

Plants that contains it

• Tithonia pedunculata

Cross-Links

• PubChem: 163013858
• LOTUS: LTS0101916
• wikiData: Q105186497