[(3S,3aR,4S,5aR,6R,9R,9aS,9bR)-9-formyl-6-hydroxy-3,5a-dimethyl-2-oxo-3,3a,4,5,6,7,8,9,9a,9b-decahydrobenzo[g][1]benzofuran-4-yl] 4-hydroxy-2-methylidenebutanoate

Details

• Internal ID: a2b0a1b3-99d5-40ce-9bcb-24ecefef8a9c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3S,3aR,4S,5aR,6R,9R,9aS,9bR)-9-formyl-6-hydroxy-3,5a-dimethyl-2-oxo-3,3a,4,5,6,7,8,9,9a,9b-decahydrobenzo[g][1]benzofuran-4-yl] 4-hydroxy-2-methylidenebutanoate
• SMILES (Canonical): CC1C2C(CC3(C(CCC(C3C2OC1=O)C=O)O)C)OC(=O)C(=C)CCO
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@H](C[C@]3([C@@H](CC[C@H]([C@@H]3[C@H]2OC1=O)C=O)O)C)OC(=O)C(=C)CCO
• InChI: InChI=1S/C20H28O7/c1-10(6-7-21)18(24)26-13-8-20(3)14(23)5-4-12(9-22)16(20)17-15(13)11(2)19(25)27-17/h9,11-17,21,23H,1,4-8H2,2-3H3/t11-,12-,13-,14+,15+,16+,17-,20-/m0/s1
• InChI Key: OWTWBLYOTMJQME-SQFWDQPPSA-N
• Popularity: 0 references 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): 110.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.01
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9892	98.92%
Caco-2	-	0.6515	65.15%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8028	80.28%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8620	86.20%
OATP1B3 inhibitior	+	0.9462	94.62%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.5130	51.30%
BSEP inhibitior	-	0.5593	55.93%
P-glycoprotein inhibitior	-	0.6439	64.39%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6856	68.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8848	88.48%
CYP3A4 inhibition	+	0.6015	60.15%
CYP2C9 inhibition	-	0.8470	84.70%
CYP2C19 inhibition	-	0.9306	93.06%
CYP2D6 inhibition	-	0.9433	94.33%
CYP1A2 inhibition	-	0.8236	82.36%
CYP2C8 inhibition	-	0.6644	66.44%
CYP inhibitory promiscuity	-	0.8654	86.54%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6099	60.99%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9596	95.96%
Skin irritation	+	0.5052	50.52%
Skin corrosion	-	0.9350	93.50%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4636	46.36%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.8914	89.14%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.7254	72.54%
Acute Oral Toxicity (c)	III	0.3695	36.95%
Estrogen receptor binding	+	0.8951	89.51%
Androgen receptor binding	+	0.5334	53.34%
Thyroid receptor binding	+	0.6536	65.36%
Glucocorticoid receptor binding	+	0.8169	81.69%
Aromatase binding	+	0.7254	72.54%
PPAR gamma	+	0.5782	57.82%
Honey bee toxicity	-	0.7712	77.12%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9936	99.36%

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	97.66%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.02%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	94.34%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.21%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.07%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.46%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.65%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.08%	94.45%
CHEMBL2581	P07339	Cathepsin D	86.11%	98.95%
CHEMBL1871	P10275	Androgen Receptor	85.99%	96.43%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.47%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.34%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	82.37%	92.50%
CHEMBL340	P08684	Cytochrome P450 3A4	81.69%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.58%	94.33%
CHEMBL5555	O00767	Acyl-CoA desaturase	81.32%	97.50%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.54%	90.08%
CHEMBL1937	Q92769	Histone deacetylase 2	80.48%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.13%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.11%	95.50%

Plants that contains it

• Centaurea pullata

Cross-Links

• PubChem: 162939508
• LOTUS: LTS0103194
• wikiData: Q105202294