[(3S,3aS,5aR,6R,9aS,9bS)-3,5a-dimethyl-2-oxo-9-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,3a,4,5,6,7,9a,9b-octahydrobenzo[g][1]benzofuran-6-yl] 2-(4-hydroxyphenyl)acetate

Details

• Internal ID: a3e7817b-23b3-4f60-94f6-6b1defddbbf8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3S,3aS,5aR,6R,9aS,9bS)-3,5a-dimethyl-2-oxo-9-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,3a,4,5,6,7,9a,9b-octahydrobenzo[g][1]benzofuran-6-yl] 2-(4-hydroxyphenyl)acetate
• SMILES (Canonical): CC1C2CCC3(C(CC=C(C3C2OC1=O)COC4C(C(C(C(O4)CO)O)O)O)OC(=O)CC5=CC=C(C=C5)O)C
• SMILES (Isomeric): C[C@H]1[C@@H]2CC[C@]3([C@@H](CC=C([C@@H]3[C@H]2OC1=O)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC(=O)CC5=CC=C(C=C5)O)C
• InChI: InChI=1S/C29H38O11/c1-14-18-9-10-29(2)20(39-21(32)11-15-3-6-17(31)7-4-15)8-5-16(22(29)26(18)40-27(14)36)13-37-28-25(35)24(34)23(33)19(12-30)38-28/h3-7,14,18-20,22-26,28,30-31,33-35H,8-13H2,1-2H3/t14-,18-,19+,20+,22+,23+,24-,25+,26-,28+,29-/m0/s1
• InChI Key: JWHRVXKSKJAGEA-DTSUCMDSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₈O₁₁
• Molecular Weight: 562.60 g/mol
• Exact Mass: 562.24141202 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.59
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8075	80.75%
Caco-2	-	0.8613	86.13%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8491	84.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8081	80.81%
OATP1B3 inhibitior	+	0.8973	89.73%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6771	67.71%
BSEP inhibitior	+	0.8822	88.22%
P-glycoprotein inhibitior	-	0.4598	45.98%
P-glycoprotein substrate	-	0.5116	51.16%
CYP3A4 substrate	+	0.7282	72.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8732	87.32%
CYP3A4 inhibition	-	0.8241	82.41%
CYP2C9 inhibition	-	0.8785	87.85%
CYP2C19 inhibition	-	0.8537	85.37%
CYP2D6 inhibition	-	0.9128	91.28%
CYP1A2 inhibition	-	0.7829	78.29%
CYP2C8 inhibition	+	0.6722	67.22%
CYP inhibitory promiscuity	-	0.8270	82.70%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5686	56.86%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9479	94.79%
Skin irritation	-	0.6474	64.74%
Skin corrosion	-	0.9391	93.91%
Ames mutagenesis	-	0.7137	71.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.3705	37.05%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7101	71.01%
skin sensitisation	-	0.9044	90.44%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6536	65.36%
Acute Oral Toxicity (c)	I	0.6394	63.94%
Estrogen receptor binding	+	0.8251	82.51%
Androgen receptor binding	+	0.7218	72.18%
Thyroid receptor binding	-	0.5260	52.60%
Glucocorticoid receptor binding	+	0.6965	69.65%
Aromatase binding	+	0.5936	59.36%
PPAR gamma	+	0.6471	64.71%
Honey bee toxicity	-	0.7130	71.30%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6750	67.50%
Fish aquatic toxicity	+	0.9913	99.13%

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	99.01%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.78%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.59%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.86%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.30%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.56%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.18%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.72%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.38%	94.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	87.52%	90.08%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.29%	99.17%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	85.87%	85.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.61%	97.25%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.44%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.78%	96.21%
CHEMBL5255	O00206	Toll-like receptor 4	83.70%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.47%	86.33%

Plants that contains it

• Sonchus arvensis

Cross-Links

• PubChem: 162964882
• LOTUS: LTS0134145
• wikiData: Q105136157