6-hydroxy-9-(hydroxymethyl)-5a-methyl-3-methylidene-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one

Details

• Internal ID: 846f3612-d8f9-442f-aebe-55d2bf0e2ce4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 6-hydroxy-9-(hydroxymethyl)-5a-methyl-3-methylidene-4,5,6,7,8,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC12CCC3C(C1=C(CCC2O)CO)OC(=O)C3=C
• SMILES (Isomeric): CC12CCC3C(C1=C(CCC2O)CO)OC(=O)C3=C
• InChI: InChI=1S/C15H20O4/c1-8-10-5-6-15(2)11(17)4-3-9(7-16)12(15)13(10)19-14(8)18/h10-11,13,16-17H,1,3-7H2,2H3
• InChI Key: PKQIXCPUGBPWSG-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 1.33
• 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	+	0.7356	73.56%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7798	77.98%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.8456	84.56%
OATP1B3 inhibitior	+	0.9526	95.26%
MATE1 inhibitior	-	0.9012	90.12%
OCT2 inhibitior	+	0.5785	57.85%
BSEP inhibitior	-	0.9622	96.22%
P-glycoprotein inhibitior	-	0.9111	91.11%
P-glycoprotein substrate	-	0.8905	89.05%
CYP3A4 substrate	+	0.6103	61.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8459	84.59%
CYP3A4 inhibition	-	0.5592	55.92%
CYP2C9 inhibition	-	0.9062	90.62%
CYP2C19 inhibition	-	0.8635	86.35%
CYP2D6 inhibition	-	0.9222	92.22%
CYP1A2 inhibition	-	0.8322	83.22%
CYP2C8 inhibition	-	0.7107	71.07%
CYP inhibitory promiscuity	-	0.8360	83.60%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5248	52.48%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.5187	51.87%
Skin irritation	+	0.5483	54.83%
Skin corrosion	-	0.9355	93.55%
Ames mutagenesis	-	0.7670	76.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5495	54.95%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.5899	58.99%
skin sensitisation	-	0.8735	87.35%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5722	57.22%
Acute Oral Toxicity (c)	III	0.6319	63.19%
Estrogen receptor binding	-	0.5932	59.32%
Androgen receptor binding	-	0.5749	57.49%
Thyroid receptor binding	-	0.5782	57.82%
Glucocorticoid receptor binding	+	0.5859	58.59%
Aromatase binding	-	0.6034	60.34%
PPAR gamma	-	0.6579	65.79%
Honey bee toxicity	-	0.8816	88.16%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9913	99.13%

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	93.36%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.34%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.10%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.77%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	89.74%	97.79%
CHEMBL2581	P07339	Cathepsin D	88.86%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.11%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.72%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.67%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.32%	85.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.18%	95.89%

Plants that contains it

• Mikania campanulata

Cross-Links

• PubChem: 73323858
• LOTUS: LTS0162164
• wikiData: Q105210563