(3S,3aS,5aR,6R,7R,9aS,9bS)-6,7-dihydroxy-3,5a,9-trimethyl-3,3a,4,5,6,7,9a,9b-octahydrobenzo[g][1]benzofuran-2-one

Details

• Internal ID: dc96e2bb-1493-4a93-9756-05693d929173
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3S,3aS,5aR,6R,7R,9aS,9bS)-6,7-dihydroxy-3,5a,9-trimethyl-3,3a,4,5,6,7,9a,9b-octahydrobenzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1C2CCC3(C(C2OC1=O)C(=CC(C3O)O)C)C
• SMILES (Isomeric): C[C@H]1[C@@H]2CC[C@@]3([C@@H]([C@H]2OC1=O)C(=C[C@H]([C@@H]3O)O)C)C
• InChI: InChI=1S/C15H22O4/c1-7-6-10(16)13(17)15(3)5-4-9-8(2)14(18)19-12(9)11(7)15/h6,8-13,16-17H,4-5H2,1-3H3/t8-,9-,10+,11+,12-,13-,15+/m0/s1
• InChI Key: YGEXJFGZYRLOHG-QZNOIVSHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.26
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9749	97.49%
Caco-2	-	0.6148	61.48%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6626	66.26%
OATP2B1 inhibitior	-	0.8540	85.40%
OATP1B1 inhibitior	+	0.9029	90.29%
OATP1B3 inhibitior	+	0.9096	90.96%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7071	70.71%
BSEP inhibitior	-	0.9693	96.93%
P-glycoprotein inhibitior	-	0.9215	92.15%
P-glycoprotein substrate	-	0.8514	85.14%
CYP3A4 substrate	+	0.6359	63.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8444	84.44%
CYP3A4 inhibition	-	0.6528	65.28%
CYP2C9 inhibition	-	0.8121	81.21%
CYP2C19 inhibition	-	0.7888	78.88%
CYP2D6 inhibition	-	0.8865	88.65%
CYP1A2 inhibition	+	0.5920	59.20%
CYP2C8 inhibition	-	0.9378	93.78%
CYP inhibitory promiscuity	-	0.7268	72.68%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4713	47.13%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9618	96.18%
Skin irritation	+	0.5695	56.95%
Skin corrosion	-	0.8609	86.09%
Ames mutagenesis	-	0.7360	73.60%
Human Ether-a-go-go-Related Gene inhibition	-	0.6177	61.77%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.6908	69.08%
skin sensitisation	-	0.6960	69.60%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5591	55.91%
Acute Oral Toxicity (c)	III	0.5524	55.24%
Estrogen receptor binding	+	0.6580	65.80%
Androgen receptor binding	+	0.6046	60.46%
Thyroid receptor binding	-	0.4915	49.15%
Glucocorticoid receptor binding	-	0.6648	66.48%
Aromatase binding	-	0.8529	85.29%
PPAR gamma	-	0.6501	65.01%
Honey bee toxicity	-	0.8082	80.82%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9850	98.50%

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	92.56%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.73%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.87%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.54%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.49%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.65%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.84%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.46%	99.23%
CHEMBL1871	P10275	Androgen Receptor	82.16%	96.43%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.53%	94.45%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.92%	93.04%

Plants that contains it

• Lactuca tatarica

Cross-Links

• PubChem: 162870025
• LOTUS: LTS0250083
• wikiData: Q105348052