[6,9-Dihydroxy-5a,9-dimethyl-5-(2-methylbut-2-enoyloxy)-3-methylidene-2-oxo-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-4-yl] 2-methylbut-2-enoate

Details

• Internal ID: 0fc5d8dc-8d3e-47a4-b48a-e435d5616e5d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [6,9-dihydroxy-5a,9-dimethyl-5-(2-methylbut-2-enoyloxy)-3-methylidene-2-oxo-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-4-yl] 2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2C(C3C(CCC(C3(C1OC(=O)C(=CC)C)C)O)(C)O)OC(=O)C2=C
• SMILES (Isomeric): CC=C(C)C(=O)OC1C2C(C3C(CCC(C3(C1OC(=O)C(=CC)C)C)O)(C)O)OC(=O)C2=C
• InChI: InChI=1S/C25H34O8/c1-8-12(3)21(27)32-18-16-14(5)23(29)31-17(16)19-24(6,30)11-10-15(26)25(19,7)20(18)33-22(28)13(4)9-2/h8-9,15-20,26,30H,5,10-11H2,1-4,6-7H3
• InChI Key: VQSLKXFKTTWCAJ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₄O₈
• Molecular Weight: 462.50 g/mol
• Exact Mass: 462.22536804 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9878	98.78%
Caco-2	-	0.5494	54.94%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6456	64.56%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.8728	87.28%
OATP1B3 inhibitior	+	0.8286	82.86%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6053	60.53%
BSEP inhibitior	+	0.6885	68.85%
P-glycoprotein inhibitior	+	0.6885	68.85%
P-glycoprotein substrate	-	0.7017	70.17%
CYP3A4 substrate	+	0.6556	65.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8910	89.10%
CYP3A4 inhibition	+	0.5339	53.39%
CYP2C9 inhibition	-	0.8634	86.34%
CYP2C19 inhibition	-	0.8997	89.97%
CYP2D6 inhibition	-	0.9433	94.33%
CYP1A2 inhibition	-	0.7277	72.77%
CYP2C8 inhibition	-	0.7254	72.54%
CYP inhibitory promiscuity	-	0.9107	91.07%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4785	47.85%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9043	90.43%
Skin irritation	+	0.5627	56.27%
Skin corrosion	-	0.8416	84.16%
Ames mutagenesis	-	0.6442	64.42%
Human Ether-a-go-go-Related Gene inhibition	-	0.3929	39.29%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.7698	76.98%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.6765	67.65%
Acute Oral Toxicity (c)	III	0.3182	31.82%
Estrogen receptor binding	+	0.8060	80.60%
Androgen receptor binding	+	0.5864	58.64%
Thyroid receptor binding	+	0.6042	60.42%
Glucocorticoid receptor binding	+	0.6284	62.84%
Aromatase binding	+	0.6252	62.52%
PPAR gamma	+	0.6796	67.96%
Honey bee toxicity	-	0.6907	69.07%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9802	98.02%

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	97.42%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.05%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	93.04%	90.17%
CHEMBL2581	P07339	Cathepsin D	92.14%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.88%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.24%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.59%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.41%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.87%	97.25%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.44%	93.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.17%	86.33%
CHEMBL1902	P62942	FK506-binding protein 1A	84.13%	97.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.74%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.72%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.67%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.03%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.84%	96.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.77%	95.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.18%	91.07%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.73%	93.03%

Plants that contains it

• Calostephane divaricata

Cross-Links

• PubChem: 162861793
• LOTUS: LTS0130485
• wikiData: Q105291478