[(3S,3aS,5aR,6R,9aS,9bS)-6-hydroxy-3,5a-dimethyl-2-oxo-3,3a,4,5,6,7,9a,9b-octahydrobenzo[g][1]benzofuran-9-yl]methyl 2-(4-methoxyphenyl)acetate

Details

• Internal ID: 297d852a-f994-4055-9cce-01de1bf233bc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3S,3aS,5aR,6R,9aS,9bS)-6-hydroxy-3,5a-dimethyl-2-oxo-3,3a,4,5,6,7,9a,9b-octahydrobenzo[g][1]benzofuran-9-yl]methyl 2-(4-methoxyphenyl)acetate
• SMILES (Canonical): CC1C2CCC3(C(CC=C(C3C2OC1=O)COC(=O)CC4=CC=C(C=C4)OC)O)C
• SMILES (Isomeric): C[C@H]1[C@@H]2CC[C@]3([C@@H](CC=C([C@@H]3[C@H]2OC1=O)COC(=O)CC4=CC=C(C=C4)OC)O)C
• InChI: InChI=1S/C24H30O6/c1-14-18-10-11-24(2)19(25)9-6-16(21(24)22(18)30-23(14)27)13-29-20(26)12-15-4-7-17(28-3)8-5-15/h4-8,14,18-19,21-22,25H,9-13H2,1-3H3/t14-,18-,19+,21+,22-,24-/m0/s1
• InChI Key: HGXKRNRXAGDTHR-RQGNXEPMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₆
• Molecular Weight: 414.50 g/mol
• Exact Mass: 414.20423867 g/mol
• Topological Polar Surface Area (TPSA): 82.10 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.07
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9946	99.46%
Caco-2	-	0.7018	70.18%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8566	85.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8804	88.04%
OATP1B3 inhibitior	+	0.9163	91.63%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6636	66.36%
BSEP inhibitior	+	0.9401	94.01%
P-glycoprotein inhibitior	+	0.7670	76.70%
P-glycoprotein substrate	-	0.6164	61.64%
CYP3A4 substrate	+	0.7285	72.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7945	79.45%
CYP3A4 inhibition	+	0.7526	75.26%
CYP2C9 inhibition	-	0.6176	61.76%
CYP2C19 inhibition	-	0.6842	68.42%
CYP2D6 inhibition	-	0.9046	90.46%
CYP1A2 inhibition	+	0.5776	57.76%
CYP2C8 inhibition	+	0.5582	55.82%
CYP inhibitory promiscuity	-	0.6532	65.32%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6049	60.49%
Eye corrosion	-	0.9942	99.42%
Eye irritation	-	0.9828	98.28%
Skin irritation	-	0.6580	65.80%
Skin corrosion	-	0.9551	95.51%
Ames mutagenesis	-	0.7137	71.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.6795	67.95%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.5774	57.74%
skin sensitisation	-	0.8937	89.37%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.8083	80.83%
Acute Oral Toxicity (c)	III	0.3506	35.06%
Estrogen receptor binding	+	0.8516	85.16%
Androgen receptor binding	+	0.7750	77.50%
Thyroid receptor binding	+	0.5552	55.52%
Glucocorticoid receptor binding	+	0.7345	73.45%
Aromatase binding	-	0.5890	58.90%
PPAR gamma	+	0.6045	60.45%
Honey bee toxicity	-	0.7924	79.24%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9968	99.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.54%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.25%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.91%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.71%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.98%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.18%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.47%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.39%	92.62%
CHEMBL2581	P07339	Cathepsin D	89.32%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.17%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.11%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.60%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.38%	96.77%
CHEMBL221	P23219	Cyclooxygenase-1	84.48%	90.17%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	84.04%	92.67%
CHEMBL3820	P35557	Hexokinase type IV	81.74%	91.96%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.68%	91.07%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.64%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.41%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.40%	97.14%

Plants that contains it

• Lactuca sativa

Cross-Links

• PubChem: 163003645
• LOTUS: LTS0040886
• wikiData: Q105028062