(3S,3aS,5aR,6R,8S,9R,9aS,9bS)-8-hydroxy-3,5a,9-trimethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,3a,4,5,6,7,8,9,9a,9b-decahydrobenzo[g][1]benzofuran-2-one

Details

• Internal ID: 9b6e6267-27bb-46ca-a049-7b9ffdf38cb5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3S,3aS,5aR,6R,8S,9R,9aS,9bS)-8-hydroxy-3,5a,9-trimethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,3a,4,5,6,7,8,9,9a,9b-decahydrobenzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1C(CC(C2(C1C3C(CC2)C(C(=O)O3)C)C)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@H](C[C@H]([C@]2([C@H]1[C@@H]3[C@@H](CC2)[C@@H](C(=O)O3)C)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C21H34O9/c1-8-10-4-5-21(3)13(6-11(23)9(2)14(21)18(10)30-19(8)27)29-20-17(26)16(25)15(24)12(7-22)28-20/h8-18,20,22-26H,4-7H2,1-3H3/t8-,9-,10-,11-,12+,13+,14+,15+,16-,17+,18-,20-,21-/m0/s1
• InChI Key: STAINRWYRZEEJG-OZTGAUEKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₄O₉
• Molecular Weight: 430.50 g/mol
• Exact Mass: 430.22028266 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): -0.83
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6667	66.67%
Caco-2	-	0.7937	79.37%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7492	74.92%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8358	83.58%
OATP1B3 inhibitior	+	0.9302	93.02%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.7954	79.54%
P-glycoprotein inhibitior	-	0.8171	81.71%
P-glycoprotein substrate	-	0.8060	80.60%
CYP3A4 substrate	+	0.6829	68.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8861	88.61%
CYP3A4 inhibition	-	0.8925	89.25%
CYP2C9 inhibition	-	0.9165	91.65%
CYP2C19 inhibition	-	0.9332	93.32%
CYP2D6 inhibition	-	0.9591	95.91%
CYP1A2 inhibition	-	0.9113	91.13%
CYP2C8 inhibition	-	0.8386	83.86%
CYP inhibitory promiscuity	-	0.9620	96.20%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6578	65.78%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9795	97.95%
Skin irritation	-	0.5573	55.73%
Skin corrosion	-	0.9447	94.47%
Ames mutagenesis	-	0.7954	79.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4896	48.96%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.6524	65.24%
skin sensitisation	-	0.9394	93.94%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6397	63.97%
Acute Oral Toxicity (c)	I	0.6730	67.30%
Estrogen receptor binding	+	0.6223	62.23%
Androgen receptor binding	+	0.5560	55.60%
Thyroid receptor binding	+	0.5756	57.56%
Glucocorticoid receptor binding	-	0.5433	54.33%
Aromatase binding	+	0.6042	60.42%
PPAR gamma	-	0.5519	55.19%
Honey bee toxicity	-	0.7134	71.34%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.8499	84.99%

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	97.40%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.17%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.63%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.90%	97.25%
CHEMBL220	P22303	Acetylcholinesterase	89.43%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.00%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.92%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.49%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.37%	89.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.31%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.08%	95.56%
CHEMBL2581	P07339	Cathepsin D	84.69%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.48%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.16%	99.23%
CHEMBL5255	O00206	Toll-like receptor 4	83.42%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.50%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.10%	96.77%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.51%	96.21%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.67%	93.04%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.65%	86.92%

Plants that contains it

• Taraxacum erythrospermum

Cross-Links

• PubChem: 163046004
• LOTUS: LTS0194856
• wikiData: Q105260078