(E)-Ethyl 3-(4-hydroxyphenyl)acrylate

Details

• Internal ID: 293c47c8-42cd-4e47-9f0c-86e0f4b6989b
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: ethyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CCOC(=O)C=CC1=CC=C(C=C1)O
• SMILES (Isomeric): CCOC(=O)/C=C/C1=CC=C(C=C1)O
• InChI: InChI=1S/C11H12O3/c1-2-14-11(13)8-5-9-3-6-10(12)7-4-9/h3-8,12H,2H2,1H3/b8-5+
• InChI Key: ZOQCEVXVQCPESC-VMPITWQZSA-N
• Popularity: 44 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.21 g/mol
• Exact Mass: 192.078644241 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 1.97
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 7362-39-2
• (E)-Ethyl 3-(4-hydroxyphenyl)acrylate
• Ethyl coumarate
• Ethyl p-Coumarate
• 2979-06-8
• Ethyl 3-(4-hydroxyphenyl)acrylate
• p-hydroxyl ethyl cinnamate
• ethyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• ethyl (E)-p-hydroxycinnamate
• CHEMBL2074640
• 2-Propenoic acid, 3-(4-hydroxyphenyl)-, ethyl ester, (2E)-
• ethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
• ethyl 3-(4-hydroxyphenyl)prop-2-enoate
• p-Hydroxycinnamic acid, ethyl ester
• p-Coumaricacidethylester
• ethyl p-hydroxycinnamate
• ethyl (E)-4-hydroxycinnamate
• Ethyl trans-4-hydroxycinnamate
• SCHEMBL1341910
• Ethyl3-(4-hydroxyphenyl)acrylate
• CHEBI:180517
• 4-Hydroxycinnamic acid ethyl ester
• DTXSID501341775
• trans-p-Coumaric acid, ethyl ester
• HY-N3103
• BDBM50428388
• MFCD00210460
• NSC408777
• s5834
• AKOS005108054
• MS-2009
• NSC-408777
• CS-0023229
• Y10121
• EN300-1453816
• A866058
• Ethyl (2E)-3-(4-hydroxyphenyl)-2-propenoate #
• 2-Propenoic acid,3-(2-hydroxyphenyl)-,ethyl ester
• Ethyl trans-4-hydroxycinnamateEthyl (E)-p-hydroxycinnamate
• (E)-Ethyl 3-(4-hydroxyphenyl)acrylate;p-Coumaric Acid Ethyl Ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8910	89.10%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8889	88.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9078	90.78%
OATP1B3 inhibitior	+	0.9717	97.17%
MATE1 inhibitior	-	0.6600	66.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7346	73.46%
P-glycoprotein inhibitior	-	0.9895	98.95%
P-glycoprotein substrate	-	0.9817	98.17%
CYP3A4 substrate	-	0.5846	58.46%
CYP2C9 substrate	-	0.7904	79.04%
CYP2D6 substrate	-	0.8750	87.50%
CYP3A4 inhibition	-	0.9406	94.06%
CYP2C9 inhibition	-	0.9181	91.81%
CYP2C19 inhibition	-	0.7880	78.80%
CYP2D6 inhibition	-	0.9558	95.58%
CYP1A2 inhibition	+	0.5603	56.03%
CYP2C8 inhibition	+	0.6261	62.61%
CYP inhibitory promiscuity	-	0.7247	72.47%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.6312	63.12%
Carcinogenicity (trinary)	Non-required	0.6178	61.78%
Eye corrosion	-	0.9153	91.53%
Eye irritation	+	0.9949	99.49%
Skin irritation	+	0.6198	61.98%
Skin corrosion	-	0.9357	93.57%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7420	74.20%
Micronuclear	-	0.6853	68.53%
Hepatotoxicity	-	0.6771	67.71%
skin sensitisation	+	0.5241	52.41%
Respiratory toxicity	-	0.9778	97.78%
Reproductive toxicity	-	0.8889	88.89%
Mitochondrial toxicity	-	0.9375	93.75%
Nephrotoxicity	+	0.4901	49.01%
Acute Oral Toxicity (c)	III	0.8714	87.14%
Estrogen receptor binding	-	0.5699	56.99%
Androgen receptor binding	+	0.7006	70.06%
Thyroid receptor binding	-	0.7444	74.44%
Glucocorticoid receptor binding	-	0.8230	82.30%
Aromatase binding	-	0.6771	67.71%
PPAR gamma	-	0.6873	68.73%
Honey bee toxicity	-	0.9473	94.73%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6755	67.55%
Fish aquatic toxicity	+	0.9595	95.95%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL261	P00915	Carbonic anhydrase I	320 nM; 320 nM	Ki; Ki	PMID: 22668600; via Super-PRED
CHEMBL205	P00918	Carbonic anhydrase II	710 nM; 710 nM	Ki; Ki	PMID: 22668600; via Super-PRED
CHEMBL3594	Q16790	Carbonic anhydrase IX	610 nM; 610 nM	Ki; Ki	PMID: 22668600; via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	850 nM; 850 nM	Ki; Ki	via Super-PRED; PMID: 22668600
CHEMBL3242	O43570	Carbonic anhydrase XII	490 nM; 490 nM	Ki; Ki	PMID: 22668600; via Super-PRED
CHEMBL3510	Q9ULX7	Carbonic anhydrase XIV	800 nM; 800 nM	Ki; Ki	via Super-PRED; PMID: 22668600

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.69%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.15%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.93%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.83%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	89.02%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.27%	99.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.43%	91.71%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	85.04%	90.93%
CHEMBL2581	P07339	Cathepsin D	83.54%	98.95%
CHEMBL3194	P02766	Transthyretin	81.02%	90.71%

Plants that contains it

• Alkekengi officinarum
• Atractylodes lancea
• Atractylodes macrocephala

Cross-Links

• PubChem: 676946
• NPASS: NPC304638
• ChEMBL: CHEMBL2074640
• LOTUS: LTS0171716
• wikiData: Q105380643