2-(4-Hydroxyphenyl)ethyl 3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 57fc7fbf-a8bb-4b8c-9397-12610de01605
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: 2-(4-hydroxyphenyl)ethyl 3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=CC=C1CCOC(=O)C=CC2=CC=C(C=C2)O)O
• SMILES (Isomeric): C1=CC(=CC=C1CCOC(=O)C=CC2=CC=C(C=C2)O)O
• InChI: InChI=1S/C17H16O4/c18-15-6-1-13(2-7-15)5-10-17(20)21-12-11-14-3-8-16(19)9-4-14/h1-10,18-19H,11-12H2
• InChI Key: ZCFLGZLKECDZFW-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.31 g/mol
• Exact Mass: 284.10485899 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 2.90
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9848	98.48%
Caco-2	+	0.7405	74.05%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.9022	90.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9235	92.35%
OATP1B3 inhibitior	+	0.9202	92.02%
MATE1 inhibitior	+	0.5600	56.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6011	60.11%
P-glycoprotein inhibitior	-	0.8775	87.75%
P-glycoprotein substrate	-	0.9317	93.17%
CYP3A4 substrate	-	0.5633	56.33%
CYP2C9 substrate	-	0.5886	58.86%
CYP2D6 substrate	-	0.8383	83.83%
CYP3A4 inhibition	-	0.7336	73.36%
CYP2C9 inhibition	-	0.5954	59.54%
CYP2C19 inhibition	+	0.7889	78.89%
CYP2D6 inhibition	-	0.9072	90.72%
CYP1A2 inhibition	+	0.7171	71.71%
CYP2C8 inhibition	+	0.7742	77.42%
CYP inhibitory promiscuity	+	0.5398	53.98%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8079	80.79%
Carcinogenicity (trinary)	Non-required	0.6315	63.15%
Eye corrosion	-	0.9921	99.21%
Eye irritation	+	0.9672	96.72%
Skin irritation	-	0.8941	89.41%
Skin corrosion	-	0.9917	99.17%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5677	56.77%
Micronuclear	-	0.7108	71.08%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8121	81.21%
Respiratory toxicity	-	0.8444	84.44%
Reproductive toxicity	-	0.6778	67.78%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.7772	77.72%
Acute Oral Toxicity (c)	III	0.7326	73.26%
Estrogen receptor binding	+	0.9159	91.59%
Androgen receptor binding	+	0.9298	92.98%
Thyroid receptor binding	-	0.6076	60.76%
Glucocorticoid receptor binding	+	0.5379	53.79%
Aromatase binding	+	0.7250	72.50%
PPAR gamma	+	0.6181	61.81%
Honey bee toxicity	-	0.8031	80.31%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9666	96.66%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3594	Q16790	Carbonic anhydrase IX	710 nM	Ki	via Super-PRED
CHEMBL4789	P35218	Carbonic anhydrase VA	850 nM	Ki	via Super-PRED
CHEMBL3969	Q9Y2D0	Carbonic anhydrase VB	620 nM	Ki	via Super-PRED
CHEMBL3025	P23280	Carbonic anhydrase VI	510 nM	Ki	via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	730 nM	Ki	via Super-PRED
CHEMBL3510	Q9ULX7	Carbonic anhydrase XIV	370 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.37%	86.33%
CHEMBL3194	P02766	Transthyretin	92.30%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.76%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.22%	94.45%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.12%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.71%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.95%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.50%	96.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.27%	91.71%
CHEMBL2581	P07339	Cathepsin D	85.97%	98.95%
CHEMBL3437	Q16853	Amine oxidase, copper containing	85.76%	94.00%

Plants that contains it

• Agnorhiza bolanderi
• Anaxagorea crassipetala
• Araujia sericifera
• Arnica nevadensis
• Artemisia gmelinii
• Beyeria sulcata var. brevipes
• Bursaria spinosa
• Chloranthus tianmushanensis
• Chromolaena odorata
• Chromolaena pulchella
• Citrus × aurantium
• Craibia grandiflora
• Dendrobium falconeri
• Dendrosenecio kilimanjari
• Dipterocarpus alatus
• Drosera peltata
• Echinops amplexicaulis
• Ficus formosana
• Gardenia fosbergii
• Goniothalamus laoticus
• Ilex affinis
• Isodon umbrosus
• Kaempferia pulchra
• Litogyne gariepina
• Odixia angusta
• Prosopis glandulosa
• Prunus laurocerasus
• Pteris plumieri
• Quercus cerris
• Salvia officinalis
• Senecio squalidus
• Seriphidium cinum
• Sesbania punicea
• Simira eliezeriana
• Sorbus pallescens
• Stenostomum lucidum
• Taxodium huegelii
• Vitex madiensis

Cross-Links

• PubChem: 86163337
• NPASS: NPC13933
• LOTUS: LTS0276228
• wikiData: Q105371071