Detailed information for compound 257842

Basic information

Technical information
  • TDR Targets ID: 257842
  • Name: 3-hydroxychromen-2-one
  • MW: 162.142 | Formula: C9H6O3
  • H donors: 1 H acceptors: 2 LogP: 1.76 Rotable bonds: 0
    Rule of 5 violations (Lipinski): 1
  • SMILES: O=c1oc2ccccc2cc1O
  • InChi: 1S/C9H6O3/c10-7-5-6-3-1-2-4-8(6)12-9(7)11/h1-5,10H
  • InChiKey: MJKVTPMWOKAVMS-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 3-hydroxy-1-benzopyran-2-one
  • 3-hydroxycoumarin
  • 3-hydroxy-2-chromenone
  • 939-19-5
  • SpecPlus_000860
  • Spectrum3_001267
  • 2H-1-Benzopyran-2-one, 3-hydroxy- (9CI)
  • 3-Hydroxy-2-benzopyrone
  • 3-Hydroxy-2H-1-benzopyran-2-one
  • 5-18-01-00376 (Beilstein Handbook Reference)
  • BRN 0128032
  • COUMARIN, 3-HYDROXY-
  • EINECS 213-355-3
  • NSC 74691
  • SPBio_000669
  • AN-829/40355682
  • 642673_ALDRICH
  • KBio1_001900
  • Spectrum4_001576
  • KBioSS_000956
  • KBio3_002334
  • Spectrum_000476
  • ST5331499
  • KBioGR_002132
  • KBio2_000956
  • Spectrum5_000232
  • KBio2_003524
  • KBio2_006092
  • DivK1c_006956
  • Spectrum2_000805
  • SPECTRUM211538
  • NSC74691
  • BSPBio_002834
  • NCGC00095536-01
  • ZINC00336205
  • SDCCGMLS-0066523.P001

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens hydroxyprostaglandin dehydrogenase 15-(NAD) Starlite/ChEMBL No references
Homo sapiens D-amino-acid oxidase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Mycobacterium ulcerans D-amino acid oxidase Aao Get druggable targets OG5_127583 All targets in OG5_127583
Schistosoma japonicum ko:K00272 D-aspartate oxidase [EC1.4.3.1], putative Get druggable targets OG5_127583 All targets in OG5_127583
Mycobacterium leprae PROBABLE D-AMINO ACID OXIDASE AAO Get druggable targets OG5_127583 All targets in OG5_127583
Candida albicans D-amino acid oxidase Get druggable targets OG5_127583 All targets in OG5_127583
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_127583 All targets in OG5_127583
Schistosoma mansoni d-amino acid oxidase Get druggable targets OG5_127583 All targets in OG5_127583
Candida albicans putative d-amino acid oxidase Get druggable targets OG5_127583 All targets in OG5_127583
Candida albicans D-amino acid oxidase Get druggable targets OG5_127583 All targets in OG5_127583
Mycobacterium tuberculosis Probable D-amino acid oxidase Aao Get druggable targets OG5_127583 All targets in OG5_127583
Candida albicans putative d-amino acid oxidase Get druggable targets OG5_127583 All targets in OG5_127583
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Mycobacterium ulcerans D-amino acid oxidase Aao D-amino-acid oxidase 347 aa 378 aa 24.6 %
Plasmodium falciparum steroid dehydrogenase, putative hydroxyprostaglandin dehydrogenase 15-(NAD) 266 aa 216 aa 22.2 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Loa Loa (eye worm) integrin beta-2 0.029 0.6244 1
Echinococcus granulosus integrin beta 2 0.029 0.6244 1
Loa Loa (eye worm) hypothetical protein 0.0195 0.3194 0.5115
Mycobacterium tuberculosis Probable D-amino acid oxidase Aao 0.0179 0.2674 0.5
Schistosoma mansoni integrin beta subunit 0.023 0.4338 0.4338
Echinococcus multilocularis integrin beta 2 0.029 0.6244 1
Mycobacterium leprae PROBABLE D-AMINO ACID OXIDASE AAO 0.0195 0.3194 0.5
Mycobacterium ulcerans D-amino acid oxidase Aao 0.0195 0.3194 0.5
Schistosoma mansoni d-amino acid oxidase 0.0195 0.3194 0.3194
Brugia malayi Integrin beta pat-3 precursor 0.029 0.6244 1

Activities

Activity type Activity value Assay description Source Reference
Activity (binding) Binding affinity to corpus collosum myelin in central nervous system of mouse at 100 uM after 20 mins by fluorescent microscopy ChEMBL. 21391687
Activity (binding) Binding affinity to human recombinant N-terminal His-tagged DAO expressed in Escherichia coli BL21(DE3) at 40 uM after 2 to 30 mins by absorption spectra analysis ChEMBL. 23391306
Activity (functional) = 5.3 % Induction of apoptosis in human U937 cells at 250 uM after 24 hrs ChEMBL. 18060791
Activity (functional) = 5.3 % Induction of apoptosis in human U937 cells at 250 uM after 24 hrs ChEMBL. 18060791
CC50 (functional) > 2000 uM Cytotoxicity against human U937 cells by trypan blue assay after 48 hrs ChEMBL. 18060791
CC50 (functional) > 2000 uM Cytotoxicity against human U937 cells by trypan blue assay after 48 hrs ChEMBL. 18060791
CD (binding) = 1.5 uM Ability to induce NAD(P)H quinone reductase activity in cultured Hepa 1c1c7 murine hepatoma cells. ChEMBL. 9857096
CD (binding) = 1.5 uM Ability to induce NAD(P)H quinone reductase activity in cultured Hepa 1c1c7 murine hepatoma cells. ChEMBL. 9857096
FC (binding) = 0.94 Activation of Nrf2 in human HSC3-ARE9 cells assessed as increase of ARE-mediated luciferase expression at 50 uM after 24 hrs relative to control ChEMBL. 26519930
IC50 (binding) = 7.46 Competitive inhibition of human recombinant DAAO after 1 hr by coupled enzyme assay in presence of D-serine ChEMBL. 23631755
IC50 (binding) = 0.44 uM Inhibition of human recombinant N-terminal His-tagged DAO expressed in Escherichia coli BL21(DE3) using D-serine as substrate by colorimetric assay ChEMBL. 23391306
IC50 (binding) = 0.943 uM Inhibition of human recombinant N-terminal His-tagged DAO expressed in Escherichia coli BL21(DE3) using D-alanine as substrate by colorimetric assay ChEMBL. 23391306
IC50 (binding) = 62 uM Inhibition human recombinant aldose reductase 1 by spectrophotometric analysis ChEMBL. 20805028
IC50 (binding) = 106 uM Inhibition sorbitol dehydrogenase by spectrophotometric analysis ChEMBL. 20805028
IC50 (binding) = 131 uM Inhibition of xanthine oxidase ChEMBL. 17316915
IC50 (binding) = 131 uM Inhibition of xanthine oxidase ChEMBL. 17316915
IC50 (functional) > 2000 uM Growth inhibition of human U937 cells by [3H]thymidine incorporation assay ChEMBL. 18060791
IC50 (functional) > 2000 uM Growth inhibition of human U937 cells by [3H]thymidine incorporation assay ChEMBL. 18060791
IC50 (binding) = 7579 uM Inhibition of human recombinant N-terminal His-tagged DDO expressed in Escherichia coli BL21(DE3) using D-aspartate as substrate by colorimetric assay ChEMBL. 23391306
IC50 (binding) > 10000 uM Inhibition of human recombinant N-terminal His-tagged serine racemase expressed in Escherichia coli BL21(DE3) using L-serine as substrate after 10 mins by fluorescence assay ChEMBL. 23391306
Inhibition (binding) Inhibition of human recombinant DAO expressed in G418-resistant HEK293/NEO cells assessed as effect on D-alanine level at 83 uM incubated for 30 mins prior to D-alanine addition measured after 24 hrs by HPLC analysis relative to vehicle-treated control ChEMBL. 23391306
Inhibition (binding) Inhibition of human recombinant N-terminal His-tagged DAO expressed in Escherichia coli BL21(DE3) using D-serine as substrate by colorimetric assay ChEMBL. 23391306
Inhibition (binding) Inhibition of human recombinant N-terminal His-tagged DDO expressed in Escherichia coli BL21(DE3) using D-aspartate as substrate by colorimetric assay ChEMBL. 23391306
Inhibition (binding) Inhibition of human recombinant N-terminal His-tagged DAO expressed in Escherichia coli BL21(DE3) using D-alanine as substrate by colorimetric assay ChEMBL. 23391306
Inhibition (binding) Inhibition of N-terminal HA-tagged human recombinant DAO overexpressed in G418-resistant HEK293 cells assessed as increase in D-alanine levels at 83 uM incubated for 30 mins prior to D-alanine addition measured after 24 hrs by HPLC analysis relative to vehicle-treated control ChEMBL. 23391306
Inhibition (binding) Competitive inhibition of human recombinant N-terminal His-tagged DAO expressed in Escherichia coli BL21(DE3) using D-alanine as substrate by Lineweaver-Burk plot analysis ChEMBL. 23391306
Inhibition (binding) Inhibition of human recombinant N-terminal His-tagged serine racemase expressed in Escherichia coli BL21(DE3) using L-serine as substrate after 10 mins by fluorescence assay ChEMBL. 23391306
Inhibition (ADMET) = 116.7288245 % Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM ChEMBL. 23571415
Inhibition (ADMET) = 126.8474101 % Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM ChEMBL. 23571415
Kd (binding) = 4 uM Binding affinity to human recombinant DAAO at 443 nm spectral modification by spectrophotometric analysis in presence of FAD ChEMBL. 23631755
Kd (binding) = 5.6 uM Binding affinity to human recombinant DAAO at 496 nm spectral modification by spectrophotometric analysis in presence of FAD ChEMBL. 23631755
Kd (binding) = 6.3 uM Binding affinity to human recombinant DAAO by stopped flow spectrophotometric analysis in presence of FAD ChEMBL. 23631755
Ki (binding) = 13 nM Competitive inhibition of human recombinant DAAO by Michaelis-Menten plot analysis in presence of D-serine ChEMBL. 23631755
Ki (binding) = 0.156 uM Inhibition of human recombinant N-terminal His-tagged DAO expressed in Escherichia coli BL21(DE3) using D-serine as substrate by Lineweaver-Burk plot analysis ChEMBL. 23391306
Kinact (binding) = 0.508 uM Inhibition of human CA9 by CO2 hydration assay ChEMBL. 20580555
Kinact (binding) = 9.6 uM Inhibition of human CA12 by CO2 hydration assay ChEMBL. 20580555
Kinact (binding) = 79.4 uM Inhibition of human CA1 by CO2 hydration assay ChEMBL. 20580555
Kinact (binding) > 100 uM Inhibition of human CA2 by CO2 hydration assay ChEMBL. 20580555
Potency (functional) = 17.7828 um PUBCHEM_BIOASSAY: qHTS Assay for Inhibitors of HPGD (15-Hydroxyprostaglandin Dehydrogenase). (Class of assay: confirmatory) [Related pubchem assays: 2429 (Confirmation qHTS Assay for Inhibitors of HPGD (15-Hydroxyprostaglandin Dehydrogenase)), 2407 (Probe Development Summary for Inhibitors of HPGD (15-Hydroxyprostaglandin Dehydrogenase)), 2427 (Thermal Shift Assay for Inhibitors of HPGD (15-Hydroxyprostaglandin Dehydrogenase))] ChEMBL. No reference

Phenotypes

Whole-cell/tissue/organism interactions

We have no records of whole-cell/tissue assays done with this compound What does this mean?

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.

External resources for this compound

Bibliographic References

10 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.