[(3aS,4S,5aR,6R,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-2-oxo-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate

Details

• Internal ID: 3418b845-6243-40c1-8119-5c81fe3d1647
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3aS,4S,5aR,6R,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-2-oxo-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate
• SMILES (Canonical): CC1C(O1)(C)C(=O)OC2CC3(C(CCC(=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](CCC(=C3[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/h11-14,16,21H,2,6-8H2,1,3-5H3/t11-,12-,13+,14-,16-,19-,20-/m0/s1
• InChI Key: AFRTUXMOKYWHEU-BEKHJFFYSA-N
• Popularity: 0 references 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: 1.50
• Atomic LogP (AlogP): 2.05
• 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	+	0.9911	99.11%
Caco-2	+	0.6265	62.65%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7685	76.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9062	90.62%
OATP1B3 inhibitior	+	0.8187	81.87%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6303	63.03%
BSEP inhibitior	-	0.9066	90.66%
P-glycoprotein inhibitior	-	0.5797	57.97%
P-glycoprotein substrate	-	0.7048	70.48%
CYP3A4 substrate	+	0.6767	67.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8556	85.56%
CYP3A4 inhibition	+	0.5671	56.71%
CYP2C9 inhibition	-	0.7550	75.50%
CYP2C19 inhibition	-	0.8694	86.94%
CYP2D6 inhibition	-	0.9468	94.68%
CYP1A2 inhibition	-	0.7000	70.00%
CYP2C8 inhibition	-	0.7199	71.99%
CYP inhibitory promiscuity	-	0.9554	95.54%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4692	46.92%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.8992	89.92%
Skin irritation	+	0.5475	54.75%
Skin corrosion	-	0.8974	89.74%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5221	52.21%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.5408	54.08%
skin sensitisation	-	0.8244	82.44%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.5560	55.60%
Acute Oral Toxicity (c)	III	0.3412	34.12%
Estrogen receptor binding	+	0.7293	72.93%
Androgen receptor binding	+	0.5862	58.62%
Thyroid receptor binding	+	0.6766	67.66%
Glucocorticoid receptor binding	+	0.7918	79.18%
Aromatase binding	+	0.6615	66.15%
PPAR gamma	+	0.5320	53.20%
Honey bee toxicity	-	0.7422	74.22%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9948	99.48%

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	93.29%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.68%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.74%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.34%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.28%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.15%	100.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.70%	93.03%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.82%	92.94%
CHEMBL2581	P07339	Cathepsin D	83.47%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.22%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.81%	95.89%
CHEMBL259	P32245	Melanocortin receptor 4	82.79%	95.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.37%	97.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.35%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.31%	86.33%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.09%	97.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.03%	93.56%
CHEMBL340	P08684	Cytochrome P450 3A4	81.02%	91.19%
CHEMBL1871	P10275	Androgen Receptor	80.98%	96.43%

Plants that contains it

• Tithonia pedunculata

Cross-Links

• PubChem: 163010574
• LOTUS: LTS0062164
• wikiData: Q104911459