Detailed information for compound 230218
Basic information
Technical information
- TDR Targets ID: 230218
- Name: benzyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoa te
- MW: 270.28 | Formula: C16H14O4
-
H donors: 2
H acceptors: 3
LogP: 2.98
Rotable bonds: 5
Rule of 5 violations (Lipinski): 1 - SMILES: O=C(OCc1ccccc1)/C=C/c1ccc(c(c1)O)O
- 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+
- InChiKey: WWVKQTNONPWVEL-VQHVLOKHSA-N
Network
Hover on a compound node to display the structore
Synonyms
- (E)-3-(3,4-dihydroxyphenyl)-2-propenoic acid benzyl ester
- phenylmethyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
- (E)-3-(3,4-dihydroxyphenyl)acrylic acid benzyl ester
- caffeic acid phenethyl ester
- benzyl caffeate
- phenylmethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
- 3-(3,4-dihydroxyphenyl)prop-2-enoic acid phenylmethyl ester
- (E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid phenylmethyl ester
- 3-(3,4-dihydroxyphenyl)acrylic acid benzyl ester
- 107843-77-6
- NSC 666590
- Phenylmethyl 3-(3,4-dihydroxyphenyl)-2-Propenoate
- Phenylmethyl caffeate
- NCI60_023208
- AIDS-085230
- AIDS085230
- Benzyl 3,4-dihydroxycinnamate
- NSC666590
- MEGxp0_000689
- 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, phenylmethyl ester
Targets
Known targets for this compound
| Species | Target name | Source | Bibliographic reference |
|---|---|---|---|
| Homo sapiens | transthyretin | Starlite/ChEMBL | References |
| Homo sapiens | aldo-keto reductase family 1, member B1 (aldose reductase) | Starlite/ChEMBL | References |
| Homo sapiens | aldo-keto reductase family 1, member B10 (aldose reductase) | Starlite/ChEMBL | References |
| Human immunodeficiency virus 1 | Human immunodeficiency virus type 1 integrase | Starlite/ChEMBL | References |
Predicted pathogen targets for this compound
By orthology
By sequence similarity to non orthologous known druggable targets
| Species | Potential target | Known druggable target | Length | Alignment span | Identity |
|---|---|---|---|---|---|
| Mycobacterium tuberculosis | Conserved protein | aldo-keto reductase family 1, member B1 (aldose reductase) | 316 aa | 325 aa | 24.6 % |
| Mycobacterium tuberculosis | Conserved protein | aldo-keto reductase family 1, member B10 (aldose reductase) | 316 aa | 331 aa | 22.4 % |
Obtained from network model
Ranking Plot
Putative Targets List
| Species | Potential target | Raw | Global | Species |
|---|---|---|---|---|
| Entamoeba histolytica | aldose reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Trichomonas vaginalis | aldo-keto reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Brugia malayi | oxidoreductase, aldo/keto reductase family protein | 0.0077 | 0.2886 | 0.5 |
| Leishmania major | prostaglandin f2-alpha synthase/D-arabinose dehydrogenase | 0.0077 | 0.2886 | 0.5 |
| Trichomonas vaginalis | aldo-keto reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Leishmania major | aldehyde reductase, putative,oxidoreductase, putative | 0.0077 | 0.2886 | 0.5 |
| Trichomonas vaginalis | dihydrodiol dehydrogenase, putative | 0.0077 | 0.2886 | 0.5 |
| Loa Loa (eye worm) | oxidoreductase | 0.0077 | 0.2886 | 0.5 |
| Trypanosoma cruzi | aldo/keto reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Trypanosoma brucei | RNA helicase, putative | 0.0125 | 0.9202 | 1 |
| Onchocerca volvulus | 0.0077 | 0.2886 | 0.5 | |
| Trypanosoma cruzi | aldo-keto reductase | 0.0077 | 0.2886 | 0.5 |
| Echinococcus multilocularis | aldo keto reductase family 1, member B4 | 0.0077 | 0.2886 | 1 |
| Echinococcus granulosus | aldo keto reductase family 1 member B4 | 0.0077 | 0.2886 | 1 |
| Brugia malayi | oxidoreductase, aldo/keto reductase family protein | 0.0077 | 0.2886 | 0.5 |
| Trichomonas vaginalis | aldo-keto reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Echinococcus multilocularis | aldo keto reductase | 0.0077 | 0.2886 | 1 |
| Echinococcus multilocularis | aldo keto reductase | 0.0077 | 0.2886 | 1 |
| Echinococcus multilocularis | aldo keto reductase family 1, member B4 | 0.0077 | 0.2886 | 1 |
| Trichomonas vaginalis | dihydrodiol dehydrogenase, putative | 0.0077 | 0.2886 | 0.5 |
| Echinococcus granulosus | aldo keto reductase family 1 member B4 | 0.0077 | 0.2886 | 1 |
| Entamoeba histolytica | aldose reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Brugia malayi | oxidoreductase, aldo/keto reductase family protein | 0.0077 | 0.2886 | 0.5 |
| Echinococcus multilocularis | aldo keto reductase family 1, member B4 | 0.0077 | 0.2886 | 1 |
| Trichomonas vaginalis | aldo-keto reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Echinococcus granulosus | aldo keto reductase family 1 member B4 | 0.0077 | 0.2886 | 1 |
| Trichomonas vaginalis | aldo-keto reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Echinococcus granulosus | aldo keto reductase | 0.0077 | 0.2886 | 1 |
| Echinococcus granulosus | aldo keto reductase family 1 member B4 | 0.0077 | 0.2886 | 1 |
| Loa Loa (eye worm) | oxidoreductase | 0.0077 | 0.2886 | 0.5 |
| Trichomonas vaginalis | aldo-keto reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Onchocerca volvulus | 0.0077 | 0.2886 | 0.5 | |
| Loa Loa (eye worm) | oxidoreductase | 0.0077 | 0.2886 | 0.5 |
| Onchocerca volvulus | 0.0077 | 0.2886 | 0.5 | |
| Mycobacterium leprae | PROBABLE OXIDOREDUCTASE | 0.0077 | 0.2886 | 1 |
| Trichomonas vaginalis | dihydrodiol dehydrogenase, putative | 0.0077 | 0.2886 | 0.5 |
| Giardia lamblia | Aldose reductase | 0.0077 | 0.2886 | 0.5 |
| Echinococcus multilocularis | aldo keto reductase | 0.0077 | 0.2886 | 1 |
| Trichomonas vaginalis | aldo-keto reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Entamoeba histolytica | aldose reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Leishmania major | aldo-keto reductase-like protein | 0.0077 | 0.2886 | 0.5 |
| Trichomonas vaginalis | aldo/keto reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Echinococcus multilocularis | aldo keto reductase family 1, member B4 | 0.0077 | 0.2886 | 1 |
| Onchocerca volvulus | 0.0077 | 0.2886 | 0.5 | |
| Echinococcus granulosus | aldo keto reductase family 1 member B4 | 0.0077 | 0.2886 | 1 |
| Echinococcus multilocularis | aldo keto reductase family 1, member B4 | 0.0077 | 0.2886 | 1 |
| Echinococcus granulosus | aldo keto reductase | 0.0077 | 0.2886 | 1 |
| Echinococcus multilocularis | aldo keto reductase family 1, member B4 | 0.0077 | 0.2886 | 1 |
| Trichomonas vaginalis | aldo/keto reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Onchocerca volvulus | 0.0077 | 0.2886 | 0.5 | |
| Echinococcus multilocularis | aldo keto reductase family 1, member B4 | 0.0077 | 0.2886 | 1 |
| Leishmania major | prostaglandin f synthase, putative | 0.0077 | 0.2886 | 0.5 |
| Echinococcus multilocularis | aldo keto reductase family 1, member B4 | 0.0077 | 0.2886 | 1 |
| Trichomonas vaginalis | aldo/keto reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Trichomonas vaginalis | aldo-keto reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Echinococcus granulosus | aldo keto reductase family 1 member B4 | 0.0077 | 0.2886 | 1 |
| Trichomonas vaginalis | aldo-keto reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Echinococcus granulosus | aldo keto reductase family 1 member B4 | 0.0077 | 0.2886 | 1 |
| Loa Loa (eye worm) | oxidoreductase | 0.0077 | 0.2886 | 0.5 |
| Mycobacterium tuberculosis | Probable oxidoreductase | 0.0077 | 0.2886 | 0.5 |
| Echinococcus granulosus | hypothetical protein | 0.0077 | 0.2886 | 1 |
| Echinococcus multilocularis | aldo keto reductase | 0.0077 | 0.2886 | 1 |
| Trichomonas vaginalis | aldo-keto reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Schistosoma mansoni | hypothetical protein | 0.0125 | 0.9202 | 1 |
| Echinococcus granulosus | aldo keto reductase | 0.0077 | 0.2886 | 1 |
| Echinococcus multilocularis | aldo keto reductase family 1, member B4 | 0.0077 | 0.2886 | 1 |
| Echinococcus multilocularis | aldo keto reductase family 1, member B4 | 0.0077 | 0.2886 | 1 |
| Loa Loa (eye worm) | hypothetical protein | 0.0077 | 0.2886 | 0.5 |
| Echinococcus granulosus | aldo keto reductase family 1 member B4 | 0.0077 | 0.2886 | 1 |
| Trichomonas vaginalis | aldo-keto reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Giardia lamblia | Aldose reductase | 0.0077 | 0.2886 | 0.5 |
| Onchocerca volvulus | 0.0077 | 0.2886 | 0.5 | |
| Loa Loa (eye worm) | oxidoreductase | 0.0077 | 0.2886 | 0.5 |
| Echinococcus multilocularis | aldo keto reductase family 1, member B4 | 0.0077 | 0.2886 | 1 |
| Echinococcus granulosus | aldo keto reductase family 1 member B4 | 0.0077 | 0.2886 | 1 |
| Trichomonas vaginalis | aldo-keto reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Toxoplasma gondii | aldose reductase, putative | 0.0077 | 0.2886 | 0.5 |
| Brugia malayi | oxidoreductase, aldo/keto reductase family protein | 0.0077 | 0.2886 | 0.5 |
Activities
| Activity type | Activity value | Assay description | Source | Reference |
|---|---|---|---|---|
| Activity (binding) | Competitive binding to TTR V30M mutant (unknown origin) expressed in Escherichia coli at 1 to 80 uM by fluorescence assay | ChEMBL. | 25314129 | |
| EC50 (functional) | = 0.347 uM | Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells assessed as nitrite accumulation administered 1 hr before LPS challenge and measured after 24 hrs by Griess reagent assay | ChEMBL. | 18667320 |
| EC50 (functional) | = 2.33 uM | Antiproliferative activity against human HeLa cells after 72 hrs by MTT assay | ChEMBL. | 12027739 |
| EC50 (functional) | = 9.74 uM | Antiproliferative activity against human HT1080 cells after 72 hrs by MTT assay | ChEMBL. | 12027739 |
| EC50 (binding) | = 16 uM | Inhibition of TTR V30M mutant (unknown origin) expressed in Escherichia coli assessed as inhibition of amyloid fibril formation by fluorescence assay | ChEMBL. | 25314129 |
| EC50 (functional) | = 35 uM | Antiproliferative activity against human A549 cells after 72 hrs by MTT assay | ChEMBL. | 12027739 |
| EC50 (ADMET) | = 38.8 uM | Cytotoxicity against mouse RAW264.7 cells assessed as cell survival after 24 hrs by MTT assay | ChEMBL. | 18667320 |
| GI50 (functional) | -6.028 | PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the HL-60(TB) Leukemia cell line. (Class of assay: confirmatory) | ChEMBL. | No reference |
| GI50 (functional) | -5.357 | PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the MDA-N Breast cell line. (Class of assay: confirmatory) | ChEMBL. | No reference |
| GI50 (functional) | -5.151 | PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the SF-539 Central Nervous System cell line. (Class of assay: confirmatory) | ChEMBL. | No reference |
| GI50 (functional) | -5.012 | PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the SK-MEL-5 Melanoma cell line. (Class of assay: confirmatory) | ChEMBL. | No reference |
| GI50 (functional) | -4.937 | PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the SN12C Renal cell line. (Class of assay: confirmatory) | ChEMBL. | No reference |
| GI50 (functional) | -4.928 | PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the ACHN Renal cell line. (Class of assay: confirmatory) | ChEMBL. | No reference |
| GI50 (functional) | -4.862 | PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the UO-31 Renal cell line. (Class of assay: confirmatory) | ChEMBL. | No reference |
| GI50 (functional) | -4.829 | PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the NCI-H23 Non-Small Cell Lung cell line. (Class of assay: confirmatory) | ChEMBL. | No reference |
| GI50 (functional) | -4.82 | PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the DU-145 Prostate cell line. (Class of assay: confirmatory) | ChEMBL. | No reference |
| GI50 (functional) | -4.79 | PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the HOP-92 Non-Small Cell Lung cell line. (Class of assay: confirmatory) | ChEMBL. | No reference |
| IC50 (binding) | = -5.05 | Inhibitory activity against HIV-1 Integrase (HIV-1-IN) | ChEMBL. | 11831895 |
| IC50 (binding) | = 210 nM | Inhibition of human recombinant N-terminus His6-tagged AKR1B10 expressed in Escherichia coli BL21 DE3 assessed as pyridine-3-aldehyde reduction by spectrometric analysis | ChEMBL. | 22236472 |
| IC50 (binding) | = 400 nM | Inhibition of human recombinant N-terminus His6-tagged AKR1B1 expressed in Escherichia coli BL21 DE3 assessed as pyridine-3-aldehyde reduction by spectrometric analysis | ChEMBL. | 22236472 |
| IC50 (binding) | = 9 uM | In vitro inhibitory activity against HIV-1 integrase. | ChEMBL. | 7473544 |
| IC50 (binding) | = 9 uM | In vitro inhibitory activity against HIV-1 integrase. | ChEMBL. | 7473544 |
| IC50 (functional) | = 14.1 uM | Cytotoxicity against human MCF7 cells by MTT assay | ChEMBL. | 18952420 |
| IC50 (functional) | = 17.4 uM | Cytotoxicity against human Bel7402 cells by MTT assay | ChEMBL. | 18952420 |
| IC50 (functional) | = 27.3 uM | Cytotoxicity against human A549 cells by MTT assay | ChEMBL. | 18952420 |
| IC50 (functional) | = 45.6 uM | Cytotoxicity against human LNCAP cells assessed as reduction in cell viability after 24 hrs by WST-1 assay | ChEMBL. | 24080105 |
| IC50 (functional) | = 74.27 uM | Antitumor activity against human SiHa cells assessed as inhibition of cell growth by MTT assay | ChEMBL. | 25160837 |
| IC50 (binding) | > 100 uM | Inhibition of HIV1 integrase by ELISA | ChEMBL. | 18952420 |
| Inhibition (functional) | = 8.8 % | Antinociceptive activity in Swiss mouse by inhibition of acetic acid-induced abdominal constriction at 10 mg/kg, ip after 20 mins | ChEMBL. | 19628311 |
| Log IC50 (binding) | = 5.05 | Inhibitory activity against HIV-1 Integrase (HIV-1-IN) | ChEMBL. | 11831895 |
Phenotypes
Whole-cell/tissue/organism interactions
| Species name | Source | Reference | Is orphan |
|---|---|---|---|
| Homo sapiens | ChEMBL23 | 12027739 | |
| Mus musculus | ChEMBL23 | 18667320 |
Many chemical entities in TDR Targets come from high-throughput screenings with whole cells or tissue samples, and not all assayed compounds have been tested against a single a single target protein, probably because they get ruled out during screening process. Even if these compounds may have not been of interest in the original screening, they may come as interesting leads for other screening assays. Furthermore, we may be able to propose drug-target associations using chemical similarities and network patterns.
Annotated phenotypes:
We have no manually annotated phenotypes for this drug.
What does this mean? / Care to help?
In TDR Targets, information about phenotypes that are caused by
drugs, or by genetic manipulation of cells (e.g. gene knockouts or
knockdowns) is manually curated from the literature. These
descriptions help to describe the potential of the target for drug
development. If no information is available for this gene or if the
information is incomplete, this may mean that i) the papers
containing this information either appeared after the curation
effort for this organism was carried out or they were inadvertently
missed by curators; or that ii) the curation effort for this
organism has not yet started.
In any case, if you have information about papers containing relevant validation data for this target, please log in using your TDR Targets username and password and send them to us using the corresponding form in this page (only visible to registered users) or contact us.
In any case, if you have information about papers containing relevant validation data for this target, please log in using your TDR Targets username and password and send them to us using the corresponding form in this page (only visible to registered users) or contact us.
External resources for this compound
- Search by CAS
- ChEMBL: CHEMBL133714
- PubChem: 5919576
Bibliographic References
5 literature references were collected for this gene.
If you have references for this compound, please enter them in a user comment (below) or Contact us.