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

Details

• Internal ID: b2a90b64-d18d-4e48-b90a-1d179313d36c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aS,5aR,6R,8S,9R,9aS,9bS)-8-hydroxy-5a,9-dimethyl-3-methylidene-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6,7,8,9,9a,9b-octahydro-3aH-benzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1C(CC(C2(C1C3C(CC2)C(=C)C(=O)O3)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(=C)C(=O)O3)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C21H32O9/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/h9-18,20,22-26H,1,4-7H2,2-3H3/t9-,10-,11-,12+,13+,14+,15+,16-,17+,18-,20-,21-/m0/s1
• InChI Key: CEDACXINXNXTDF-PNTLOSRKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₂O₉
• Molecular Weight: 428.50 g/mol
• Exact Mass: 428.20463259 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -0.91
• 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	+	0.8236	82.36%
Caco-2	-	0.7672	76.72%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7837	78.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7844	78.44%
OATP1B3 inhibitior	+	0.9278	92.78%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.7241	72.41%
P-glycoprotein inhibitior	-	0.7740	77.40%
P-glycoprotein substrate	-	0.8235	82.35%
CYP3A4 substrate	+	0.6900	69.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8749	87.49%
CYP3A4 inhibition	-	0.8453	84.53%
CYP2C9 inhibition	-	0.8998	89.98%
CYP2C19 inhibition	-	0.9171	91.71%
CYP2D6 inhibition	-	0.9258	92.58%
CYP1A2 inhibition	-	0.8805	88.05%
CYP2C8 inhibition	-	0.6488	64.88%
CYP inhibitory promiscuity	-	0.9195	91.95%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6359	63.59%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9732	97.32%
Skin irritation	+	0.5704	57.04%
Skin corrosion	-	0.9379	93.79%
Ames mutagenesis	-	0.7224	72.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.7277	72.77%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.7025	70.25%
skin sensitisation	-	0.9019	90.19%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.6296	62.96%
Acute Oral Toxicity (c)	I	0.6216	62.16%
Estrogen receptor binding	+	0.6814	68.14%
Androgen receptor binding	+	0.6041	60.41%
Thyroid receptor binding	+	0.5686	56.86%
Glucocorticoid receptor binding	+	0.5480	54.80%
Aromatase binding	+	0.5962	59.62%
PPAR gamma	+	0.5850	58.50%
Honey bee toxicity	-	0.7057	70.57%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9742	97.42%

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	97.38%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.52%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.91%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.44%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.21%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.64%	86.33%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.56%	96.61%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.38%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	87.12%	97.79%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.85%	100.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.61%	95.83%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.91%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.51%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.11%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.05%	94.45%
CHEMBL2581	P07339	Cathepsin D	83.70%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.29%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.65%	94.00%

Plants that contains it

• Taraxacum erythrospermum

Cross-Links

• PubChem: 101034643
• LOTUS: LTS0270954
• wikiData: Q104955523