Ethyl p-methoxycinnamate

Details

• Internal ID: 2b6a7d7b-d2bb-410a-ad78-0c717e60000a
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid esters
• IUPAC Name: ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): CCOC(=O)C=CC1=CC=C(C=C1)OC
• SMILES (Isomeric): CCOC(=O)/C=C/C1=CC=C(C=C1)OC
• InChI: InChI=1S/C12H14O3/c1-3-15-12(13)9-6-10-4-7-11(14-2)8-5-10/h4-9H,3H2,1-2H3/b9-6+
• InChI Key: DHNGCHLFKUPGPX-RMKNXTFCSA-N
• Popularity: 101 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₄O₃
• Molecular Weight: 206.24 g/mol
• Exact Mass: 206.094294304 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.27
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• Ethyl 4-Methoxycinnamate
• Ethyl p-methoxycinnamate
• 4-Methoxycinnamic Acid Ethyl Ester
• (E)-Ethyl 3-(4-methoxyphenyl)acrylate
• 1929-30-2
• Ethyl 3-(4-methoxyphenyl)acrylate
• Ethyl methoxycinnamate
• Ethyl trans-p-methoxycinnamate
• Solaboost SPF
• ethyl trans-4-methoxycinnamate
• Uvsob B
• Ethyl (E)-4-methoxycinnamate
• 4-Methoxy Ethyl Cinnamate
• ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
• ethyl (2E)-3-(4-methoxyphenyl)prop-2-enoate
• Ethyl (E)-p-methoxycinnamate
• Ethyl 3-(4-methoxyphenyl)-2-propenoate
• Ethyl (E)-3-(4-methoxyphenyl)-2-propenoate
• Methyl-p-coumaric acid, ethyl ester
• 3-(4-Methoxyphenyl)-2-propenoic acid, ethyl ester
• UNII-SD418S06XD
• 2-Propenoic acid, 3-(4-methoxyphenyl)-, ethyl ester
• SD418S06XD
• Ethyl (E)-3-(p-methoxyphenyl)-2-propenoate
• 3-(Methoxyphenyl)-2-propenoic acid, ethyl ester
• EINECS 217-679-6
• NSC636698
• (2E)-3-(4-Methoxyphenyl)-2-propenoic acid ethyl ester
• 2-Propenoic acid, 3-(4-methoxyphenyl)-, ethyl ester, (E)-
• 2-Propenoic acid, 3-(4-methoxyphenyl)-, ethyl ester, (2E)-
• AI3-05527
• ethyl (E)-3-(4-methoxyphenyl)acrylate
• (E)-Ethyl p-methoxycinnamate
• ETHYLP-METHOXYCINNAMATE
• MFCD00026906
• p-Methoxycinnamic acid ethyl ester
• EPMC
• Ethyl4-methoxycinnamate
• Ethyl p- methoxycinnamate
• ethyl para-methoxycinnamate
• p-Methoxyl methyl cinnamate
• SCHEMBL15190
• (e)-ethyl-p-methoxycinnamate
• CHEMBL95956
• SCHEMBL1056347
• Ethyl 4-methoxy-trans-cinnamate
• Ethyl3-(4-methoxyphenyl)acrylate
• DTXSID401308962
• HMS3886P22
• BDBM50486903
• ETHYL METHOXYCINNAMATE [INCI]
• NSC 26462
• NSC 44831
• s9350
• AKOS005070817
• CCG-266623
• NSC-636698
• (E)-4-Methoxycinnamic acid ethyl ester
• 4-Methoxybenzeneacrylic acid ethyl ester
• trans-4-Methoxycinnamic acid ethyl ester
• AC-29413
• 3-(4-Methoxyphenyl)acrylic Acid Ethyl Ester
• M1204
• 3-(4-methoxy-phenyl)-acrylic acid ethyl ester
• Ethyl (2E)-3-(4-methoxyphenyl)-2-propenoate
• EN300-1453807
• 6Z-0282
• A877939
• A880299
• Ethyl trans-4-methoxycinnamate, analytical standard
• J-502027
• Q-100958
• Q27289147
• Z53833826
• (E)-3-(4-Methoxyphenyl)-2-propenoic acid ethyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9430	94.30%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.9016	90.16%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9490	94.90%
OATP1B3 inhibitior	+	0.9725	97.25%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.4734	47.34%
P-glycoprotein inhibitior	-	0.9821	98.21%
P-glycoprotein substrate	-	0.9861	98.61%
CYP3A4 substrate	-	0.5687	56.87%
CYP2C9 substrate	-	0.7982	79.82%
CYP2D6 substrate	-	0.8644	86.44%
CYP3A4 inhibition	-	0.9282	92.82%
CYP2C9 inhibition	-	0.9355	93.55%
CYP2C19 inhibition	-	0.8036	80.36%
CYP2D6 inhibition	-	0.9509	95.09%
CYP1A2 inhibition	+	0.8150	81.50%
CYP2C8 inhibition	-	0.6826	68.26%
CYP inhibitory promiscuity	+	0.5121	51.21%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6342	63.42%
Carcinogenicity (trinary)	Non-required	0.6448	64.48%
Eye corrosion	-	0.8278	82.78%
Eye irritation	+	0.9847	98.47%
Skin irritation	-	0.5584	55.84%
Skin corrosion	-	0.9848	98.48%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4609	46.09%
Micronuclear	-	0.7593	75.93%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.5659	56.59%
Respiratory toxicity	-	0.9333	93.33%
Reproductive toxicity	-	0.6556	65.56%
Mitochondrial toxicity	-	0.9500	95.00%
Nephrotoxicity	-	0.6531	65.31%
Acute Oral Toxicity (c)	III	0.8565	85.65%
Estrogen receptor binding	-	0.4885	48.85%
Androgen receptor binding	+	0.6293	62.93%
Thyroid receptor binding	-	0.7477	74.77%
Glucocorticoid receptor binding	-	0.7057	70.57%
Aromatase binding	+	0.5524	55.24%
PPAR gamma	-	0.9098	90.98%
Honey bee toxicity	-	0.9635	96.35%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9531	95.31%

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	95.43%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.17%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	94.55%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.74%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.64%	86.33%
CHEMBL4208	P20618	Proteasome component C5	89.49%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.75%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	85.11%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.46%	96.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.07%	93.99%

Plants that contains it

• Curcuma kwangsiensis
• Curcuma phaeocaulis
• Curcuma wenyujin
• Curcuma zedoaria
• Dalbergia odorifera
• Eucommia ulmoides
• Hedychium spicatum
• Kaempferia galanga

Cross-Links

• PubChem: 5281783
• NPASS: NPC179686
• ChEMBL: CHEMBL95956
• LOTUS: LTS0171262
• wikiData: Q27289147