[(3aS,4S,5S,5aR,6R,9S,9aS,9bR)-5,6,9-trihydroxy-5a,9-dimethyl-3-methylidene-2-oxo-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 88c909f1-cb0e-49c4-966f-a9ac40cc316d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3aS,4S,5S,5aR,6R,9S,9aS,9bR)-5,6,9-trihydroxy-5a,9-dimethyl-3-methylidene-2-oxo-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2C(C3C(CCC(C3(C1O)C)O)(C)O)OC(=O)C2=C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1[C@@H]2[C@H]([C@H]3[C@@](CC[C@H]([C@@]3([C@@H]1O)C)O)(C)O)OC(=O)C2=C
• InChI: InChI=1S/C20H28O7/c1-6-9(2)17(23)27-14-12-10(3)18(24)26-13(12)15-19(4,25)8-7-11(21)20(15,5)16(14)22/h6,11-16,21-22,25H,3,7-8H2,1-2,4-5H3/b9-6-/t11-,12+,13-,14+,15+,16-,19+,20+/m1/s1
• InChI Key: SVFPCVAHUZWSGH-YFWDXGNQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₇
• Molecular Weight: 380.40 g/mol
• Exact Mass: 380.18350323 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.86
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9594	95.94%
Caco-2	-	0.5795	57.95%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6017	60.17%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8767	87.67%
OATP1B3 inhibitior	+	0.8657	86.57%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6124	61.24%
BSEP inhibitior	-	0.8574	85.74%
P-glycoprotein inhibitior	-	0.6933	69.33%
P-glycoprotein substrate	-	0.7316	73.16%
CYP3A4 substrate	+	0.6635	66.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8910	89.10%
CYP3A4 inhibition	+	0.5346	53.46%
CYP2C9 inhibition	-	0.8333	83.33%
CYP2C19 inhibition	-	0.8640	86.40%
CYP2D6 inhibition	-	0.9292	92.92%
CYP1A2 inhibition	-	0.7688	76.88%
CYP2C8 inhibition	-	0.7767	77.67%
CYP inhibitory promiscuity	-	0.8351	83.51%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5037	50.37%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9424	94.24%
Skin irritation	+	0.5601	56.01%
Skin corrosion	-	0.8568	85.68%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4605	46.05%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8080	80.80%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.6293	62.93%
Acute Oral Toxicity (c)	III	0.3894	38.94%
Estrogen receptor binding	+	0.7279	72.79%
Androgen receptor binding	-	0.4883	48.83%
Thyroid receptor binding	+	0.6449	64.49%
Glucocorticoid receptor binding	+	0.6296	62.96%
Aromatase binding	+	0.5996	59.96%
PPAR gamma	+	0.5698	56.98%
Honey bee toxicity	-	0.7123	71.23%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9776	97.76%

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	97.17%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.33%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.31%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.79%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.17%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.86%	95.89%
CHEMBL2581	P07339	Cathepsin D	84.84%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.49%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.05%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.64%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.42%	97.25%
CHEMBL1902	P62942	FK506-binding protein 1A	83.07%	97.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.46%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.43%	96.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.28%	97.14%
CHEMBL221	P23219	Cyclooxygenase-1	80.65%	90.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.38%	91.07%
CHEMBL340	P08684	Cytochrome P450 3A4	80.35%	91.19%

Plants that contains it

• Calostephane divaricata

Cross-Links

• PubChem: 162955523
• LOTUS: LTS0068635
• wikiData: Q105261934