[(3aR,4R,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] (3R)-3-hydroxy-2-methylidenebutanoate

Details

• Internal ID: 8c8c7257-ba93-4bb6-9530-8371f15551c2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3aR,4R,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] (3R)-3-hydroxy-2-methylidenebutanoate
• InChI: InChI=1S/C20H26O6/c1-9-6-7-14(22)20(5)8-13(25-18(23)10(2)12(4)21)15-11(3)19(24)26-17(15)16(9)20/h12-15,17,21-22H,2-3,6-8H2,1,4-5H3/t12-,13-,14-,15-,17+,20+/m1/s1
• InChI Key: USMGBEDASIFJNA-MNIPYMMXSA-N
• Popularity: 2 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): 93.10 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.81
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9933	99.33%
Caco-2	+	0.5530	55.30%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7595	75.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9043	90.43%
OATP1B3 inhibitior	-	0.2130	21.30%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6053	60.53%
BSEP inhibitior	-	0.9256	92.56%
P-glycoprotein inhibitior	-	0.6693	66.93%
P-glycoprotein substrate	-	0.6566	65.66%
CYP3A4 substrate	+	0.6621	66.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8532	85.32%
CYP3A4 inhibition	+	0.5382	53.82%
CYP2C9 inhibition	-	0.8088	80.88%
CYP2C19 inhibition	-	0.9234	92.34%
CYP2D6 inhibition	-	0.9594	95.94%
CYP1A2 inhibition	-	0.6652	66.52%
CYP2C8 inhibition	-	0.7234	72.34%
CYP inhibitory promiscuity	-	0.9391	93.91%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5239	52.39%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.8345	83.45%
Skin irritation	+	0.6055	60.55%
Skin corrosion	-	0.9089	90.89%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4781	47.81%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.6033	60.33%
skin sensitisation	-	0.8161	81.61%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.5355	53.55%
Acute Oral Toxicity (c)	I	0.4184	41.84%
Estrogen receptor binding	+	0.6336	63.36%
Androgen receptor binding	-	0.4899	48.99%
Thyroid receptor binding	+	0.5809	58.09%
Glucocorticoid receptor binding	+	0.6689	66.89%
Aromatase binding	-	0.4909	49.09%
PPAR gamma	-	0.4945	49.45%
Honey bee toxicity	-	0.6502	65.02%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9970	99.70%

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	96.09%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.95%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.75%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.77%	99.23%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	91.64%	96.47%
CHEMBL4040	P28482	MAP kinase ERK2	91.48%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.83%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	89.64%	90.17%
CHEMBL2581	P07339	Cathepsin D	87.96%	98.95%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	87.75%	95.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.09%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.54%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.96%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.81%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.52%	96.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.32%	93.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.32%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.24%	97.09%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.32%	98.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.33%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	81.23%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.86%	91.07%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.54%	94.33%

Plants that contains it

• Tithonia rotundifolia

Cross-Links

• PubChem: 162980729
• LOTUS: LTS0046770
• wikiData: Q105278291