2-[(5R,6S,7aS)-6-ethenyl-7a-hydroxy-3,6-dimethyl-2-oxo-5,7-dihydro-4H-1-benzofuran-5-yl]prop-2-enoic acid

Details

• Internal ID: 9a86e6c4-f50f-443b-95db-e018948e49e5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: 2-[(5R,6S,7aS)-6-ethenyl-7a-hydroxy-3,6-dimethyl-2-oxo-5,7-dihydro-4H-1-benzofuran-5-yl]prop-2-enoic acid
• InChI: InChI=1S/C15H18O5/c1-5-14(4)7-15(19)11(9(3)13(18)20-15)6-10(14)8(2)12(16)17/h5,10,19H,1-2,6-7H2,3-4H3,(H,16,17)/t10-,14+,15-/m0/s1
• InChI Key: LCYXSLKTAYHKQA-VQISRLSMSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.79
• 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	+	0.9883	98.83%
Caco-2	-	0.6518	65.18%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7063	70.63%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.8927	89.27%
OATP1B3 inhibitior	+	0.9302	93.02%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8674	86.74%
P-glycoprotein inhibitior	-	0.9402	94.02%
P-glycoprotein substrate	-	0.8684	86.84%
CYP3A4 substrate	+	0.5743	57.43%
CYP2C9 substrate	-	0.8042	80.42%
CYP2D6 substrate	-	0.9000	90.00%
CYP3A4 inhibition	-	0.6393	63.93%
CYP2C9 inhibition	-	0.8850	88.50%
CYP2C19 inhibition	-	0.9259	92.59%
CYP2D6 inhibition	-	0.9512	95.12%
CYP1A2 inhibition	-	0.7529	75.29%
CYP2C8 inhibition	-	0.7903	79.03%
CYP inhibitory promiscuity	-	0.9355	93.55%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4573	45.73%
Eye corrosion	-	0.9823	98.23%
Eye irritation	-	0.7899	78.99%
Skin irritation	+	0.5418	54.18%
Skin corrosion	-	0.8507	85.07%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5546	55.46%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.6951	69.51%
skin sensitisation	-	0.7385	73.85%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.8010	80.10%
Acute Oral Toxicity (c)	I	0.3382	33.82%
Estrogen receptor binding	-	0.5601	56.01%
Androgen receptor binding	+	0.6043	60.43%
Thyroid receptor binding	-	0.6126	61.26%
Glucocorticoid receptor binding	-	0.6176	61.76%
Aromatase binding	-	0.6039	60.39%
PPAR gamma	+	0.6407	64.07%
Honey bee toxicity	-	0.8873	88.73%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9928	99.28%

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	95.75%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.61%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.45%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.26%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.52%	99.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.98%	93.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.63%	96.09%
CHEMBL1902	P62942	FK506-binding protein 1A	82.39%	97.05%
CHEMBL5028	O14672	ADAM10	82.09%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	80.63%	91.19%
CHEMBL1951	P21397	Monoamine oxidase A	80.52%	91.49%

Plants that contains it

• Neolitsea aciculata
• Neolitsea hiiranensis

Cross-Links

• PubChem: 163045963
• LOTUS: LTS0247107
• wikiData: Q105150078