Phenylethyl 3-methylcaffeate

Details

• Internal ID: 5aafed5a-c619-49b9-8c84-58a932b333ac
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: 2-phenylethyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OCCC2=CC=CC=C2)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)OCCC2=CC=CC=C2)O
• InChI: InChI=1S/C18H18O4/c1-21-17-13-15(7-9-16(17)19)8-10-18(20)22-12-11-14-5-3-2-4-6-14/h2-10,13,19H,11-12H2,1H3/b10-8+
• InChI Key: CZQNYPBIOHVQQN-CSKARUKUSA-N
• Popularity: 14 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₈O₄
• Molecular Weight: 298.30 g/mol
• Exact Mass: 298.12050905 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.20
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• Phenylethyl 3-methylcaffeate
• Phenyethyl 3-methylcaffeate
• Phenylethyl-3-methylcaffeate
• CCRIS 7791
• Caffeic Acid 3-Methyl Phenethyl Ester
• 2-Phenylethyl 3-(4-hydroxy-3-methoxyphenyl)-2-propenoate
• CHEMBL442022
• 2-phenylethyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• NSC666255
• B49B43355J
• NSC-666255
• NSC-671193
• 2-phenylethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, 2-phenylethyl ester
• phenethyl 3-(4-hydroxy-3-methoxyphenyl)acrylate
• 2-phenylethyl (2E)-3-[4-hydroxy-3-(methyloxy)phenyl]prop-2-enoate
• 2-Phenylethyl Ferulate
• Ferulic Acid Phenethyl Ester
• Phenetyl ferulate
• phenylethyl ferulate
• beta-Phenethyl ferulate
• phenethyl-trans-ferulate
• DTXSID8021143
• SCHEMBL14259660
• UNII-B49B43355J
• BDBM50029216
• MFCD18385026
• NSC671193
• 3-methylcaffeic acid phenylethyl ester
• AKOS015966757
• AKOS040760769
• CS-W009964
• HY-W009248
• CAFFEICACID,3-METHYLPHENETHYLESTER
• MS-24287
• LS-184855
• .beta.-Phenylethyl 4-hydroxy-3-methoxycinnamate
• 4-Hydroxy-3-methoxycinnamic acid phenethyl ester
• Q27464606
• phenethyl (E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoate
• 3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid phenethyl ester
• (E)-3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid phenethyl ester
• 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, 2-phenylethyl ester, (2E)-
• 132335-98-9

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9881	98.81%
Caco-2	+	0.6690	66.90%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.9244	92.44%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.9126	91.26%
OATP1B3 inhibitior	+	0.9659	96.59%
MATE1 inhibitior	-	0.5600	56.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9280	92.80%
P-glycoprotein inhibitior	-	0.8360	83.60%
P-glycoprotein substrate	-	0.8846	88.46%
CYP3A4 substrate	+	0.5056	50.56%
CYP2C9 substrate	-	0.7914	79.14%
CYP2D6 substrate	-	0.8167	81.67%
CYP3A4 inhibition	-	0.7771	77.71%
CYP2C9 inhibition	+	0.6915	69.15%
CYP2C19 inhibition	+	0.7037	70.37%
CYP2D6 inhibition	-	0.9032	90.32%
CYP1A2 inhibition	+	0.7357	73.57%
CYP2C8 inhibition	+	0.8860	88.60%
CYP inhibitory promiscuity	-	0.5184	51.84%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7971	79.71%
Carcinogenicity (trinary)	Non-required	0.6984	69.84%
Eye corrosion	-	0.9850	98.50%
Eye irritation	+	0.6136	61.36%
Skin irritation	-	0.8058	80.58%
Skin corrosion	-	0.9850	98.50%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7057	70.57%
Micronuclear	-	0.6816	68.16%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8847	88.47%
Respiratory toxicity	-	0.8222	82.22%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	-	0.9000	90.00%
Nephrotoxicity	-	0.8910	89.10%
Acute Oral Toxicity (c)	III	0.7858	78.58%
Estrogen receptor binding	+	0.9494	94.94%
Androgen receptor binding	+	0.9150	91.50%
Thyroid receptor binding	-	0.5540	55.40%
Glucocorticoid receptor binding	+	0.6900	69.00%
Aromatase binding	+	0.8210	82.10%
PPAR gamma	+	0.5325	53.25%
Honey bee toxicity	-	0.8940	89.40%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9569	95.69%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3194	P02766	Transthyretin	7900 nM	EC50	PMID: 25314129

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.64%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.13%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.81%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.93%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.06%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	93.05%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.16%	99.17%
CHEMBL2581	P07339	Cathepsin D	89.84%	98.95%
CHEMBL3194	P02766	Transthyretin	88.79%	90.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.99%	95.50%
CHEMBL2535	P11166	Glucose transporter	84.91%	98.75%
CHEMBL221	P23219	Cyclooxygenase-1	83.08%	90.17%
CHEMBL1255126	O15151	Protein Mdm4	82.11%	90.20%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.90%	91.71%
CHEMBL4208	P20618	Proteasome component C5	81.32%	90.00%

Plants that contains it

• Hansenia forbesii
• Hansenia weberbaueriana
• Pteronia paniculata

Cross-Links

• PubChem: 5284444
• NPASS: NPC120225
• ChEMBL: CHEMBL442022
• LOTUS: LTS0270566
• wikiData: Q27464606