Benzyl caffeate

Details

• Internal ID: 392dc3ca-b69e-42e6-9cb7-fe04c25b1335
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: benzyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC=C(C=C1)COC(=O)C=CC2=CC(=C(C=C2)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)COC(=O)/C=C/C2=CC(=C(C=C2)O)O
• InChI: InChI=1S/C16H14O4/c17-14-8-6-12(10-15(14)18)7-9-16(19)20-11-13-4-2-1-3-5-13/h1-10,17-18H,11H2/b9-7+
• InChI Key: WWVKQTNONPWVEL-VQHVLOKHSA-N
• Popularity: 34 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₄
• Molecular Weight: 270.28 g/mol
• Exact Mass: 270.08920892 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 3.10

Synonyms

• (E)-Benzyl 3-(3,4-dihydroxyphenyl)acrylate
• 107843-77-6
• Caffeic Acid Benzyl Ester
• 130734-47-3
• benzyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CaffeicAcidBenzylEster-d5
• BD29SJL432
• CHEMBL133714
• NSC666590
• NSC-666590
• Benzyl 3-(3,4-Dihydroxyphenyl)Acrylate
• benzyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• Phenylmethyl caffeate
• 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, phenylmethyl ester
• NSC 666590
• UNII-BD29SJL432
• Phenylmethyl 3-(3,4-dihydroxyphenyl)-2-Propenoate
• Benzyl 3,4-dihydroxycinnamate
• MEGxp0_000689
• BDBM50029198
• (E)-Benzyl3-(3,4-dihydroxyphenyl)acrylate
• CS-0363076
• Benzyl (E)-3-(3,4-dihydroxyphenyl)acrylate
• A801008
• Phenylmethyl 1-(3',4'-Dihydroxyphenyl)Propenate
• 3-(3,4-Dihydroxy-phenyl)-acrylic acid benzyl ester
• J-501993
• Phenylmethyl 1-(3'',4''-dihydroxyphenyl)propenate
• (E)-3-(3,4-Dihydroxy-phenyl)-acrylic acid benzyl ester
• 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, phenylmethyl ester, (2Z)-
• benzyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate;Phenethyl 3-(3,4-Dihydroxyphenyl)acrylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5983	O60218	Aldo-keto reductase family 1 member B10	210 nM	IC50	via Super-PRED
CHEMBL1900	P15121	Aldose reductase	400 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.39%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.03%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.84%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.51%	99.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	93.11%	91.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.92%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.02%	94.62%
CHEMBL2581	P07339	Cathepsin D	90.48%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.11%	95.50%
CHEMBL3194	P02766	Transthyretin	87.14%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.92%	99.15%
CHEMBL221	P23219	Cyclooxygenase-1	86.87%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.61%	96.09%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.31%	80.78%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.97%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	82.64%	94.73%

Plants that contains it

• Baccharis sarothroides
• Populus deltoides
• Populus laurifolia
• Populus tremuloides
• Populus violascens

Cross-Links

• PubChem: 5919576
• LOTUS: LTS0228896
• wikiData: Q104383832