(3R,4S)-4-ethenyl-3-(3-hydroxy-3-phenylprop-2-enoyl)-4-methyloxolan-2-one

Details

• Internal ID: 48340591-df02-413a-a2b0-c26b2cd37ae5
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Styrenes
• IUPAC Name: (3R,4S)-4-ethenyl-3-(3-hydroxy-3-phenylprop-2-enoyl)-4-methyloxolan-2-one
• SMILES (Canonical): CC1(COC(=O)C1C(=O)C=C(C2=CC=CC=C2)O)C=C
• SMILES (Isomeric): C[C@]1(COC(=O)[C@H]1C(=O)C=C(C2=CC=CC=C2)O)C=C
• InChI: InChI=1S/C16H16O4/c1-3-16(2)10-20-15(19)14(16)13(18)9-12(17)11-7-5-4-6-8-11/h3-9,14,17H,1,10H2,2H3/t14-,16-/m1/s1
• InChI Key: SYWQVHNVGPYUQH-GDBMZVCRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₆O₄
• Molecular Weight: 272.29 g/mol
• Exact Mass: 272.10485899 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 2.52
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9797	97.97%
Caco-2	+	0.8052	80.52%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7776	77.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9433	94.33%
OATP1B3 inhibitior	+	0.9535	95.35%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7560	75.60%
P-glycoprotein inhibitior	-	0.8601	86.01%
P-glycoprotein substrate	-	0.9077	90.77%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.8063	80.63%
CYP2D6 substrate	-	0.8978	89.78%
CYP3A4 inhibition	-	0.8709	87.09%
CYP2C9 inhibition	-	0.8224	82.24%
CYP2C19 inhibition	-	0.8325	83.25%
CYP2D6 inhibition	-	0.9608	96.08%
CYP1A2 inhibition	-	0.6931	69.31%
CYP2C8 inhibition	-	0.7636	76.36%
CYP inhibitory promiscuity	-	0.8719	87.19%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8171	81.71%
Carcinogenicity (trinary)	Non-required	0.5364	53.64%
Eye corrosion	-	0.9383	93.83%
Eye irritation	-	0.5000	50.00%
Skin irritation	-	0.5194	51.94%
Skin corrosion	-	0.8755	87.55%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7002	70.02%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	0.7250	72.50%
skin sensitisation	-	0.5775	57.75%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	-	0.5556	55.56%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	+	0.5727	57.27%
Acute Oral Toxicity (c)	III	0.6364	63.64%
Estrogen receptor binding	+	0.7320	73.20%
Androgen receptor binding	+	0.6643	66.43%
Thyroid receptor binding	+	0.5540	55.40%
Glucocorticoid receptor binding	-	0.4752	47.52%
Aromatase binding	+	0.6500	65.00%
PPAR gamma	-	0.6131	61.31%
Honey bee toxicity	-	0.9199	91.99%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9891	98.91%

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	95.69%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.74%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.86%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.37%	99.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.59%	94.62%
CHEMBL221	P23219	Cyclooxygenase-1	86.16%	90.17%
CHEMBL2581	P07339	Cathepsin D	86.11%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.91%	89.00%
CHEMBL5028	O14672	ADAM10	82.27%	97.50%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.94%	89.67%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	80.33%	89.44%

Plants that contains it

• Cratoxylum cochinchinense

Cross-Links

• PubChem: 163003395
• LOTUS: LTS0206435
• wikiData: Q105263835