6-Hydroxy-9-(hydroxymethyl)-3,5a-dimethyl-3,3a,4,5,6,7,9a,9b-octahydrobenzo[g][1]benzofuran-2-one

Details

• Internal ID: dd4baec7-9458-48c8-8b30-086254ce7d34
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 6-hydroxy-9-(hydroxymethyl)-3,5a-dimethyl-3,3a,4,5,6,7,9a,9b-octahydrobenzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1C2CCC3(C(CC=C(C3C2OC1=O)CO)O)C
• SMILES (Isomeric): CC1C2CCC3(C(CC=C(C3C2OC1=O)CO)O)C
• InChI: InChI=1S/C15H22O4/c1-8-10-5-6-15(2)11(17)4-3-9(7-16)12(15)13(10)19-14(8)18/h3,8,10-13,16-17H,4-7H2,1-2H3
• InChI Key: MTVKTTBORXMRAK-UHFFFAOYSA-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: 0.90
• Atomic LogP (AlogP): 1.26
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9900	99.00%
Caco-2	+	0.6486	64.86%
Blood Brain Barrier	-	0.5395	53.95%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8037	80.37%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.9118	91.18%
OATP1B3 inhibitior	+	0.9672	96.72%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	+	0.5436	54.36%
BSEP inhibitior	-	0.9397	93.97%
P-glycoprotein inhibitior	-	0.9495	94.95%
P-glycoprotein substrate	-	0.7723	77.23%
CYP3A4 substrate	+	0.6482	64.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8480	84.80%
CYP3A4 inhibition	+	0.5648	56.48%
CYP2C9 inhibition	-	0.9360	93.60%
CYP2C19 inhibition	-	0.9332	93.32%
CYP2D6 inhibition	-	0.9197	91.97%
CYP1A2 inhibition	-	0.8994	89.94%
CYP2C8 inhibition	-	0.9050	90.50%
CYP inhibitory promiscuity	-	0.8043	80.43%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5718	57.18%
Eye corrosion	-	0.9938	99.38%
Eye irritation	-	0.9617	96.17%
Skin irritation	+	0.5442	54.42%
Skin corrosion	-	0.9475	94.75%
Ames mutagenesis	-	0.7337	73.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6610	66.10%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.6182	61.82%
skin sensitisation	-	0.8782	87.82%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6321	63.21%
Acute Oral Toxicity (c)	III	0.6043	60.43%
Estrogen receptor binding	+	0.6272	62.72%
Androgen receptor binding	+	0.6631	66.31%
Thyroid receptor binding	+	0.5309	53.09%
Glucocorticoid receptor binding	+	0.7193	71.93%
Aromatase binding	-	0.7060	70.60%
PPAR gamma	-	0.7283	72.83%
Honey bee toxicity	-	0.8604	86.04%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9831	98.31%

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	95.30%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.43%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.31%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.82%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.15%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.55%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.79%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.67%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.29%	89.00%
CHEMBL1871	P10275	Androgen Receptor	82.10%	96.43%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.39%	93.04%

Plants that contains it

• Sonchus arvensis
• Sonchus arvensis subsp. uliginosus

Cross-Links

• PubChem: 163025111
• LOTUS: LTS0174546
• wikiData: Q105171898