(3aS,4R,5S,6R,7aR)-6-ethenyl-4-hydroxy-6-(hydroxymethyl)-3-methylidene-5-prop-1-en-2-yl-4,5,7,7a-tetrahydro-3aH-1-benzofuran-2-one

Details

• Internal ID: 6623458d-de01-45c4-8c05-a3fe6097a4cf
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3aS,4R,5S,6R,7aR)-6-ethenyl-4-hydroxy-6-(hydroxymethyl)-3-methylidene-5-prop-1-en-2-yl-4,5,7,7a-tetrahydro-3aH-1-benzofuran-2-one
• SMILES (Canonical): CC(=C)C1C(C2C(CC1(CO)C=C)OC(=O)C2=C)O
• SMILES (Isomeric): CC(=C)[C@@H]1[C@H]([C@H]2[C@@H](C[C@@]1(CO)C=C)OC(=O)C2=C)O
• InChI: InChI=1S/C15H20O4/c1-5-15(7-16)6-10-11(9(4)14(18)19-10)13(17)12(15)8(2)3/h5,10-13,16-17H,1-2,4,6-7H2,3H3/t10-,11-,12-,13+,15-/m1/s1
• InChI Key: CVSUQAVSBQBOMA-XLFUENPSSA-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: 1.90
• Atomic LogP (AlogP): 1.21
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9684	96.84%
Caco-2	-	0.8045	80.45%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6794	67.94%
OATP2B1 inhibitior	-	0.8575	85.75%
OATP1B1 inhibitior	+	0.9186	91.86%
OATP1B3 inhibitior	+	0.9462	94.62%
MATE1 inhibitior	-	0.9012	90.12%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9330	93.30%
P-glycoprotein inhibitior	-	0.9203	92.03%
P-glycoprotein substrate	-	0.8223	82.23%
CYP3A4 substrate	+	0.5492	54.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8459	84.59%
CYP3A4 inhibition	-	0.8941	89.41%
CYP2C9 inhibition	-	0.8561	85.61%
CYP2C19 inhibition	-	0.8510	85.10%
CYP2D6 inhibition	-	0.9544	95.44%
CYP1A2 inhibition	-	0.8005	80.05%
CYP2C8 inhibition	-	0.9000	90.00%
CYP inhibitory promiscuity	-	0.7310	73.10%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5466	54.66%
Eye corrosion	-	0.9783	97.83%
Eye irritation	-	0.8909	89.09%
Skin irritation	-	0.6491	64.91%
Skin corrosion	-	0.9031	90.31%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6870	68.70%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.5783	57.83%
skin sensitisation	-	0.7467	74.67%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.8820	88.20%
Acute Oral Toxicity (c)	III	0.4992	49.92%
Estrogen receptor binding	-	0.5059	50.59%
Androgen receptor binding	-	0.4819	48.19%
Thyroid receptor binding	-	0.5256	52.56%
Glucocorticoid receptor binding	+	0.5376	53.76%
Aromatase binding	-	0.7136	71.36%
PPAR gamma	-	0.5816	58.16%
Honey bee toxicity	-	0.7453	74.53%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.8410	84.10%

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	96.40%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.01%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.65%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.85%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.68%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	82.96%	90.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.89%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.74%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.67%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.50%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	81.28%	94.73%
CHEMBL4530	P00488	Coagulation factor XIII	81.17%	96.00%

Plants that contains it

• Schkuhria schkuhrioides

Cross-Links

• PubChem: 13858230
• LOTUS: LTS0090644
• wikiData: Q104970974