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

Details

• Internal ID: 9ca1b4be-a6d7-4486-994d-08e9f765d5aa
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: benzyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC=C(C=C1)COC(=O)C=CC2=CC=C(C=C2)O
• SMILES (Isomeric): C1=CC=C(C=C1)COC(=O)/C=C/C2=CC=C(C=C2)O
• InChI: InChI=1S/C16H14O3/c17-15-9-6-13(7-10-15)8-11-16(18)19-12-14-4-2-1-3-5-14/h1-11,17H,12H2/b11-8+
• InChI Key: RGZZCZQQPNJCPO-DHZHZOJOSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.28 g/mol
• Exact Mass: 254.094294304 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.15
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 61844-62-0
• (E)-Benzyl 3-(4-hydroxyphenyl)acrylate
• CHEMBL1095574
• 2-Propenoic acid, 3-(4-hydroxyphenyl)-, phenylmethyl ester, (2E)-
• benzyl-p-coumarate
• Phenylmethyl p-coumarate
• benzyl (E)-p-coumarate
• Benzyl trans-4-coumarate
• SCHEMBL4501585
• RGZZCZQQPNJCPO-DHZHZOJOSA-N
• 4-Hydroxycinnamic acid benzyl ester
• Benzyl 3-(4-Hydroxyphenyl)Acrylate
• BDBM50362850
• AKOS040761407

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9973	99.73%
Caco-2	+	0.6345	63.45%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8869	88.69%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9098	90.98%
OATP1B3 inhibitior	+	0.9195	91.95%
MATE1 inhibitior	-	0.6000	60.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.4659	46.59%
P-glycoprotein inhibitior	-	0.9555	95.55%
P-glycoprotein substrate	-	0.9743	97.43%
CYP3A4 substrate	-	0.5949	59.49%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8578	85.78%
CYP3A4 inhibition	-	0.9200	92.00%
CYP2C9 inhibition	-	0.8943	89.43%
CYP2C19 inhibition	+	0.5225	52.25%
CYP2D6 inhibition	-	0.9392	93.92%
CYP1A2 inhibition	+	0.6006	60.06%
CYP2C8 inhibition	+	0.7624	76.24%
CYP inhibitory promiscuity	+	0.5411	54.11%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.6719	67.19%
Carcinogenicity (trinary)	Non-required	0.6071	60.71%
Eye corrosion	-	0.9905	99.05%
Eye irritation	+	0.9689	96.89%
Skin irritation	-	0.6461	64.61%
Skin corrosion	-	0.9927	99.27%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4686	46.86%
Micronuclear	-	0.5493	54.93%
Hepatotoxicity	-	0.6573	65.73%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	-	0.9556	95.56%
Reproductive toxicity	-	0.8222	82.22%
Mitochondrial toxicity	-	0.8375	83.75%
Nephrotoxicity	-	0.7039	70.39%
Acute Oral Toxicity (c)	III	0.7839	78.39%
Estrogen receptor binding	+	0.8903	89.03%
Androgen receptor binding	+	0.9289	92.89%
Thyroid receptor binding	-	0.6210	62.10%
Glucocorticoid receptor binding	-	0.6990	69.90%
Aromatase binding	+	0.6972	69.72%
PPAR gamma	+	0.5668	56.68%
Honey bee toxicity	-	0.8850	88.50%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.5755	57.55%
Fish aquatic toxicity	+	0.9885	98.85%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5983	O60218	Aldo-keto reductase family 1 member B10	130 nM; 130 nM	IC50; IC50	PMID: 22236472; via Super-PRED
CHEMBL1900	P15121	Aldose reductase	2200 nM	IC50	PMID: 22236472
CHEMBL3729	P22748	Carbonic anhydrase IV	18700 nM	Ki	PMID: 26498394
CHEMBL3594	Q16790	Carbonic anhydrase IX	860 nM; 860 nM	Ki; Ki	PMID: 26498394; via Super-PRED
CHEMBL4789	P35218	Carbonic anhydrase VA	970 nM; 970 nM	Ki; Ki	PMID: 26498394; via Super-PRED
CHEMBL3969	Q9Y2D0	Carbonic anhydrase VB	800 nM; 800 nM	Ki; Ki	PMID: 26498394; via Super-PRED
CHEMBL3025	P23280	Carbonic anhydrase VI	730 nM; 730 nM	Ki; Ki	PMID: 26498394; via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	720 nM; 720 nM	Ki; Ki	PMID: 26498394; via Super-PRED
CHEMBL3242	O43570	Carbonic anhydrase XII	29400 nM	Ki	PMID: 26498394
CHEMBL3510	Q9ULX7	Carbonic anhydrase XIV	810 nM; 810 nM	Ki; Ki	via Super-PRED; PMID: 26498394

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.29%	86.33%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	93.34%	91.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.95%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.71%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.44%	91.11%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.53%	94.62%
CHEMBL2581	P07339	Cathepsin D	90.02%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.31%	95.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.23%	96.09%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.96%	89.67%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.55%	96.00%
CHEMBL221	P23219	Cyclooxygenase-1	83.29%	90.17%

Plants that contains it

• Anodendron affine
• Cedrela salvadorensis
• Eriodictyon angustifolium
• Galium latoramosum
• Garcinia gummi-gutta
• Hertia cheirifolia
• Licaria chrysophylla
• Ormosia hosiei
• Ornithoglossum viride
• Petasites radiatus
• Populus balsamifera
• Populus tremuloides
• Schizanthus tricolor
• Sphaeranthus confertifolius

Cross-Links

• PubChem: 10083644
• NPASS: NPC206341
• ChEMBL: CHEMBL1095574
• LOTUS: LTS0016937
• wikiData: Q105236207