Detailed information for compound 304071

Basic information

Technical information
  • TDR Targets ID: 304071
  • Name: (2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)me thyl]butane-1,4-diol
  • MW: 362.417 | Formula: C20H26O6
  • H donors: 4 H acceptors: 4 LogP: 2.52 Rotable bonds: 9
    Rule of 5 violations (Lipinski): 1
  • SMILES: OC[C@@H]([C@@H](Cc1ccc(c(c1)OC)O)CO)Cc1ccc(c(c1)OC)O
  • InChi: 1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16-/m0/s1
  • InChiKey: PUETUDUXMCLALY-HOTGVXAUSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (2R,3R)-2,3-bis[(4-hydroxy-3-methoxy-phenyl)methyl]butane-1,4-diol
  • (2R,3R)-2,3-divanillylbutane-1,4-diol
  • secoisolariciresinol
  • (2R,3R)-2,3-bis(4-hydroxy-3-methoxy-benzyl)butane-1,4-diol
  • 29388-59-8
  • (2R*,3R*)-2,3-Bis(4-hydroxy-3-methoxybenzyl)-1,4-butanediol
  • 60372_FLUKA
  • (R-(R*,R*))-2,3-Bis((4-hydroxy-3-methoxyphenyl)methyl)butane-1,4-diol
  • CCRIS 7790
  • EINECS 249-599-2
  • (-)-Secoisolariciresinol
  • 2,3-Bis(4-hydroxy-3-methoxybenzyl)-1,4-butanediol, (-)
  • AIDS-005043
  • AIDS005043
  • Arbo 8

Targets

Known targets for this compound

No curated genes were found associated with this compound

Predicted pathogen targets for this compound

By orthology
No druggable targets predicted by orthology data
By sequence similarity to non orthologous known druggable targets
No druggable targets predicted by sequence similarity
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Schistosoma mansoni jumonji domain containing protein 0.0089 0.1028 0.1934
Brugia malayi Thioredoxin reductase 0.0046 0.0113 0.0113
Echinococcus granulosus jumonji domain containing protein 0.0047 0.0134 0.0175
Loa Loa (eye worm) IRE protein kinase 0.0217 0.3808 0.7165
Mycobacterium leprae DIHYDROLIPOAMIDE DEHYDROGENASE LPD (LIPOAMIDE REDUCTASE (NADH)) (LIPOYL DEHYDROGENASE) (DIHYDROLIPOYL DEHYDROGENASE) (DIAPHORASE 0.0118 0.1659 1
Plasmodium falciparum thioredoxin reductase 0.0046 0.0113 1
Mycobacterium ulcerans glutaminase 0.0286 0.5315 0.5278
Entamoeba histolytica protein kinase, putative 0.0217 0.3808 0.5
Chlamydia trachomatis glutamate-1-semialdehyde-2,1-aminomutase 0.0045 0.0077 0.5
Schistosoma mansoni cellular tumor antigen P53 0.0058 0.0359 0.0676
Brugia malayi jmjC domain containing protein 0.0111 0.1525 0.1525
Echinococcus granulosus Transcription factor JmjC domain containing protein 0.0111 0.1525 0.1989
Plasmodium vivax thioredoxin reductase, putative 0.0046 0.0113 1
Schistosoma mansoni ornithine--oxo-acid transaminase 0.0045 0.0077 0.0144
Echinococcus multilocularis ornithine aminotransferase 0.0045 0.0077 0.01
Echinococcus multilocularis serine:threonine protein kinase:endoribonuclease 0.0217 0.3808 0.4966
Brugia malayi glutathione reductase 0.0046 0.0113 0.0113
Echinococcus multilocularis thioredoxin glutathione reductase 0.0046 0.0113 0.0147
Trichomonas vaginalis conserved hypothetical protein 0.011 0.1502 0.2721
Mycobacterium tuberculosis Probable dehydrogenase 0.0106 0.1403 0.1336
Mycobacterium tuberculosis Probable membrane NADH dehydrogenase NdhA 0.0106 0.1403 0.1336
Echinococcus multilocularis ornithine aminotransferase 0.0045 0.0077 0.01
Loa Loa (eye worm) glutathione reductase 0.0046 0.0113 0.0212
Echinococcus granulosus ornithine aminotransferase 0.0045 0.0077 0.01
Echinococcus granulosus serine:threonine protein kinase:endoribonuclease 0.0217 0.3808 0.4966
Plasmodium vivax glutathione reductase, putative 0.0046 0.0113 1
Loa Loa (eye worm) hypothetical protein 0.0058 0.0359 0.0676
Plasmodium falciparum glutathione reductase 0.0046 0.0113 1
Mycobacterium ulcerans L-lysine aminotransferase 0.0502 1 1
Mycobacterium tuberculosis Dihydrolipoamide dehydrogenase LpdC (lipoamide reductase (NADH)) (lipoyl dehydrogenase) (dihydrolipoyl dehydrogenase) (diaphoras 0.0118 0.1659 0.1594
Echinococcus granulosus thioredoxin glutathione reductase 0.0046 0.0113 0.0147
Mycobacterium tuberculosis Probable nitrite reductase [NAD(P)H] large subunit [FAD flavoprotein] NirB 0.0106 0.1403 0.1336
Brugia malayi glutaminase DH11.1 0.0286 0.5315 0.5315
Loa Loa (eye worm) glutaminase 2 0.0286 0.5315 1
Loa Loa (eye worm) thioredoxin reductase 0.0046 0.0113 0.0212
Trichomonas vaginalis serine threonine-protein kinase, putative 0.011 0.1502 0.2721
Echinococcus multilocularis tumor protein p63 0.0395 0.7668 1
Onchocerca volvulus 0.0058 0.0359 0.5
Echinococcus multilocularis geminin 0.0166 0.2714 0.3539
Loa Loa (eye worm) glutaminase 0.0286 0.5315 1
Schistosoma mansoni hypothetical protein 0.0166 0.2714 0.5107
Trichomonas vaginalis glutaminase, putative 0.0286 0.5315 1
Toxoplasma gondii thioredoxin reductase 0.0046 0.0113 1
Echinococcus granulosus tumor protein p63 0.0395 0.7668 1
Loa Loa (eye worm) hypothetical protein 0.0058 0.0372 0.0701
Leishmania major trypanothione reductase 0.0046 0.0113 0.5
Wolbachia endosymbiont of Brugia malayi acetylornithine transaminase protein 0.0045 0.0077 0.5
Trypanosoma cruzi trypanothione reductase, putative 0.0046 0.0113 0.5
Echinococcus multilocularis Transcription factor, JmjC domain containing protein 0.0111 0.1525 0.1989
Schistosoma mansoni hypothetical protein 0.0166 0.2714 0.5107
Mycobacterium tuberculosis Probable oxidoreductase 0.0118 0.1659 0.1594
Echinococcus granulosus geminin 0.0166 0.2714 0.3539
Mycobacterium tuberculosis NADPH-dependent mycothiol reductase Mtr 0.0046 0.0113 0.0036
Mycobacterium tuberculosis Probable reductase 0.0106 0.1403 0.1336
Schistosoma mansoni glutaminase 0.0286 0.5315 1
Mycobacterium tuberculosis NAD(P)H quinone reductase LpdA 0.0118 0.1659 0.1594
Echinococcus granulosus Aminotransferase class III 0.0045 0.0077 0.01
Loa Loa (eye worm) jmjC domain-containing protein 0.007 0.0631 0.1188
Mycobacterium leprae PROBABLE NADH DEHYDROGENASE NDH 0.0106 0.1403 0.838
Entamoeba histolytica protein kinase, putative 0.0217 0.3808 0.5
Mycobacterium tuberculosis Probable NADH dehydrogenase Ndh 0.0106 0.1403 0.1336
Echinococcus multilocularis Aminotransferase class III 0.0045 0.0077 0.01
Trypanosoma brucei trypanothione reductase 0.0046 0.0113 0.5
Echinococcus multilocularis jumonji domain containing protein 0.0047 0.0134 0.0175
Mycobacterium tuberculosis Probable L-lysine-epsilon aminotransferase Lat (L-lysine aminotransferase) (lysine 6-aminotransferase) 0.0502 1 1
Mycobacterium tuberculosis Putative ferredoxin reductase 0.0106 0.1403 0.1336
Schistosoma mansoni serine/threonine protein kinase 0.0111 0.1517 0.2854
Brugia malayi Ribonuclease 2-5A family protein 0.0217 0.3808 0.3808

Activities

Activity type Activity value Assay description Source Reference
EC50 (functional) = 5.9 ug ml-1 Antiproliferative activity against human HT1080 cells by MTT assay ChEMBL. 12444707
IC50 (binding) Inhibition of human recombinant MMP9 catalytic domain incubated for 20 mins by fluorimetric assay ChEMBL. 22658537
IC50 (binding) Inhibition of HIV1 reverse transcriptase ChEMBL. 7525878
IC50 (binding) Inhibition of human recombinant MMP2 catalytic domain incubated for 20 mins by fluorimetric assay ChEMBL. 22658537
IC50 (binding) Inhibition of human recombinant MMP3 catalytic domain incubated for 20 mins by fluorimetric assay ChEMBL. 22658537
IC50 (binding) Inhibition of human recombinant MMP13 catalytic domain incubated for 20 mins by fluorimetric assay ChEMBL. 22658537
IC50 (binding) Inhibition of human recombinant MMP12 catalytic domain incubated for 20 mins by fluorimetric assay ChEMBL. 22658537
IC50 (functional) > 5 ug ml-1 Cytotoxicity against human KB cells by colorimetric method ChEMBL. 16038539
IC50 (functional) > 5 ug ml-1 Cytotoxicity against human NCI-H187 cells by colorimetric method ChEMBL. 16038539
IC50 (functional) > 40 ug ml-1 Cytotoxicity against human A549 cells after 48 hrs by SRB assay ChEMBL. 18603435
IC50 (functional) > 40 ug ml-1 Cytotoxicity against human SK-MEL-2 cells after 48 hrs by SRB assay ChEMBL. 18603435
IC50 (functional) = 18.75 uM Anticancer activity against human XF498 cells by SRB assay ChEMBL. 21420296
IC50 (functional) = 21.47 uM Anticancer activity against human SK-MEL-2 cells by SRB assay ChEMBL. 21420296
IC50 (functional) > 30 uM Anticancer activity against human A549 cells by SRB assay ChEMBL. 21420296
IC50 (functional) > 30 uM Anticancer activity against human SKOV3 cells by SRB assay ChEMBL. 21420296
IC50 (ADMET) = 47.3 uM Inhibition of CYP3A4 after 30 mins by fluorometric assay ChEMBL. 21138310
IC50 (binding) = 50.12 uM Inhibition of human recombinant MMP1 catalytic domain incubated for 20 mins by fluorimetric assay ChEMBL. 22658537
IC50 (functional) = 87.62 uM Antiinflammatory activity in mouse BV2 cells assessed as inhibition of lipopolysaccharide induced NO production ChEMBL. 21420296
IC50 (ADMET) > 100 uM Inhibition of CYP2D6 after 30 mins by fluorometric assay ChEMBL. 21138310
IC50 (functional) > 110.4 uM Cytotoxicity against human A549 cells after 48 hrs by sulforhodamine B assay ChEMBL. 21958542
IC50 (functional) > 110.4 uM Cytotoxicity against mouse B16F10 cells after 48 hrs by sulforhodamine B assay ChEMBL. 21958542
IC50 (functional) > 110.4 uM Cytotoxicity against human HCT15 cells after 48 hrs by sulforhodamine B assay ChEMBL. 21958542
IC50 (functional) > 110.4 uM Cytotoxicity against human SKOV3 cells after 48 hrs by sulforhodamine B assay ChEMBL. 21958542
IC50 (functional) > 110.4 uM Cytotoxicity against human SK-MEL-2 cells after 48 hrs by sulforhodamine B assay ChEMBL. 21958542
IC50 (binding) = 213 uM Inhibition of xanthine oxidase ChEMBL. 16309309
IC50 (binding) = 230 uM Displacement of [3H]DHT from human serum SHBG ChEMBL. 9461660
IC50 (functional) = 0.172 uM/ml Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide production after 24 hrs ChEMBL. 18986199
Inhibition (binding) < 5 % Inhibitory activity against 3'-processing by HIV-1 Integrase at 100 microM ChEMBL. 8568830
Inhibition (binding) < 5 % Inhibitory activity against strand transfer by HIV-1 Integrase at 100 microM ChEMBL. 8568830
Inhibition (binding) < 5 % Inhibitory activity against 3'-processing by HIV-1 Integrase at 100 microM ChEMBL. 8568830
Inhibition (binding) < 5 % Inhibitory activity against strand transfer by HIV-1 Integrase at 100 microM ChEMBL. 8568830
Inhibition (binding) > 30 % Inhibition of human recombinant MMP1 catalytic domain at 10 uM incubated for 20 mins by fluorimetric assay ChEMBL. 22658537
Papp (ADMET) = 9.5 ucm/s Apparent permeability across basolateral to apical side in human Caco2 cells after 2 hrs by HPLC analysis ChEMBL. 24417583

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Homo sapiens ChEMBL23 16038539

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

5 literature references were collected for this gene.

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