[(3S,3aR,4S,5aR,9R,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-2,6-dioxo-3,3a,4,5,9a,9b-hexahydrobenzo[g][1]benzofuran-4-yl] acetate

Details

• Internal ID: 43ba8048-62bf-4a6f-b8a7-268e788ab674
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3S,3aR,4S,5aR,9R,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-2,6-dioxo-3,3a,4,5,9a,9b-hexahydrobenzo[g][1]benzofuran-4-yl] acetate
• SMILES (Canonical): CC1C2C(CC3(C(C2OC1=O)C(C=CC3=O)(C)O)C)OC(=O)C
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@H](C[C@@]3([C@@H]([C@H]2OC1=O)[C@](C=CC3=O)(C)O)C)OC(=O)C
• InChI: InChI=1S/C17H22O6/c1-8-12-10(22-9(2)18)7-16(3)11(19)5-6-17(4,21)14(16)13(12)23-15(8)20/h5-6,8,10,12-14,21H,7H2,1-4H3/t8-,10-,12+,13-,14+,16-,17+/m0/s1
• InChI Key: YFKOMLOLNDFZBJ-TTWDUYPJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₆
• Molecular Weight: 322.40 g/mol
• Exact Mass: 322.14163842 g/mol
• Topological Polar Surface Area (TPSA): 89.90 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.01
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9724	97.24%
Caco-2	-	0.5533	55.33%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5912	59.12%
OATP2B1 inhibitior	-	0.8566	85.66%
OATP1B1 inhibitior	+	0.9159	91.59%
OATP1B3 inhibitior	+	0.9090	90.90%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6852	68.52%
P-glycoprotein inhibitior	-	0.7281	72.81%
P-glycoprotein substrate	-	0.7255	72.55%
CYP3A4 substrate	+	0.6146	61.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9120	91.20%
CYP3A4 inhibition	-	0.6350	63.50%
CYP2C9 inhibition	-	0.8507	85.07%
CYP2C19 inhibition	-	0.9199	91.99%
CYP2D6 inhibition	-	0.9687	96.87%
CYP1A2 inhibition	-	0.8212	82.12%
CYP2C8 inhibition	-	0.8825	88.25%
CYP inhibitory promiscuity	-	0.8025	80.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Danger	0.3880	38.80%
Eye corrosion	-	0.9815	98.15%
Eye irritation	-	0.9043	90.43%
Skin irritation	-	0.6194	61.94%
Skin corrosion	-	0.8600	86.00%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5629	56.29%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.6283	62.83%
skin sensitisation	-	0.7680	76.80%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.4677	46.77%
Acute Oral Toxicity (c)	III	0.3263	32.63%
Estrogen receptor binding	+	0.7066	70.66%
Androgen receptor binding	+	0.5662	56.62%
Thyroid receptor binding	+	0.5676	56.76%
Glucocorticoid receptor binding	-	0.5379	53.79%
Aromatase binding	-	0.6928	69.28%
PPAR gamma	-	0.5135	51.35%
Honey bee toxicity	-	0.8031	80.31%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5950	59.50%
Fish aquatic toxicity	+	0.9614	96.14%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.56%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.38%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.96%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.89%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.82%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	86.54%	91.49%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.48%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.87%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.66%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.95%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.82%	99.23%

Plants that contains it

• Artemisia cana

Cross-Links

• PubChem: 15479021
• LOTUS: LTS0230089
• wikiData: Q105347638