(3S)-3-[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-4-methoxy-4-oxobutanoic acid

Details

• Internal ID: 871286ad-61f7-4682-be18-71b93c9fbebc
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: (3S)-3-[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-4-methoxy-4-oxobutanoic acid
• SMILES (Canonical): COC(=O)C(CC(=O)O)OC(=O)C=CC1=CC=C(C=C1)O
• SMILES (Isomeric): COC(=O)[C@H](CC(=O)O)OC(=O)/C=C\C1=CC=C(C=C1)O
• InChI: InChI=1S/C14H14O7/c1-20-14(19)11(8-12(16)17)21-13(18)7-4-9-2-5-10(15)6-3-9/h2-7,11,15H,8H2,1H3,(H,16,17)/b7-4-/t11-/m0/s1
• InChI Key: GVCNRGIEFGYOMQ-IBHLPDHGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₄O₇
• Molecular Weight: 294.26 g/mol
• Exact Mass: 294.07395278 g/mol
• Topological Polar Surface Area (TPSA): 110.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.96
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9677	96.77%
Caco-2	+	0.5556	55.56%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7962	79.62%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8959	89.59%
OATP1B3 inhibitior	+	0.9438	94.38%
MATE1 inhibitior	-	0.6600	66.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7332	73.32%
P-glycoprotein inhibitior	-	0.9002	90.02%
P-glycoprotein substrate	-	0.8211	82.11%
CYP3A4 substrate	+	0.5080	50.80%
CYP2C9 substrate	-	0.5976	59.76%
CYP2D6 substrate	-	0.8609	86.09%
CYP3A4 inhibition	-	0.8700	87.00%
CYP2C9 inhibition	-	0.8842	88.42%
CYP2C19 inhibition	-	0.9013	90.13%
CYP2D6 inhibition	-	0.9232	92.32%
CYP1A2 inhibition	-	0.9051	90.51%
CYP2C8 inhibition	+	0.6351	63.51%
CYP inhibitory promiscuity	-	0.9425	94.25%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7036	70.36%
Carcinogenicity (trinary)	Non-required	0.6015	60.15%
Eye corrosion	-	0.9263	92.63%
Eye irritation	-	0.5785	57.85%
Skin irritation	-	0.6529	65.29%
Skin corrosion	-	0.9180	91.80%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7300	73.00%
Micronuclear	+	0.6577	65.77%
Hepatotoxicity	-	0.6572	65.72%
skin sensitisation	-	0.7321	73.21%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.5752	57.52%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.6135	61.35%
Acute Oral Toxicity (c)	III	0.6255	62.55%
Estrogen receptor binding	+	0.6885	68.85%
Androgen receptor binding	+	0.8289	82.89%
Thyroid receptor binding	-	0.7088	70.88%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.5928	59.28%
PPAR gamma	-	0.8071	80.71%
Honey bee toxicity	-	0.8937	89.37%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.7981	79.81%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.67%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.54%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.39%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.12%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.79%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.15%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.74%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.13%	94.45%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	84.00%	100.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.20%	89.67%

Plants that contains it

• Pyrus pyrifolia

Cross-Links

• PubChem: 163187700
• LOTUS: LTS0239330
• wikiData: Q105021047