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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:2,3-bis(4-hydroxyphenyl)propionitrile
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Accession:CHEBI:63949 term browser browse the term
Definition:A nitrile that is acetonitrile in which one of the hydrogens is replaced by a 4-hydroxyphenyl group while a second hydrogen is replaced by a 4-hydroxybenzyl group. It is a specific agonist for estrogen receptor beta (ERbeta).
Synonyms:exact_synonym: 2,3-BHPPN ;   2,3-bis(4-hydroxyphenyl)propanenitrile;   DPN compound
 related_synonym: 2,3-bis(p-hydroxyphenyl)propionitrile;   Formula=C15H13NO2;   InChI=1S/C15H13NO2/c16-10-13(12-3-7-15(18)8-4-12)9-11-1-5-14(17)6-2-11/h1-8,13,17-18H,9H2;   InChIKey=GHZHWDWADLAOIQ-UHFFFAOYSA-N;   SMILES=Oc1ccc(CC(C#N)c2ccc(O)cc2)cc1
 alt_id: MESH:C486182
 xref: CAS:1428-67-7;   LINCS:LSM-1423
 xref_mesh: MESH:C486182
 xref: PMID:21268084;   PMID:21397017;   PMID:21636213;   PMID:21712365;   Reaxys:3337109


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2,3-bis(4-hydroxyphenyl)propionitrile term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Bcl2 BCL2, apoptosis regulator increases expression
multiple interactions
ISO 2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of BCL2 mRNA; 2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of BCL2 protein
2,3-bis(4-hydroxyphenyl)-propionitrile promotes the reaction [Chlorodiphenyl (54% Chlorine) results in decreased expression of BCL2 protein]
ESR1 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of BCL2 protein]; ESR2 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of BCL2 mRNA]
CTD PMID:19264808 PMID:24216299 NCBI chr13:26,605,426...26,769,374
Ensembl chr13:26,605,426...26,769,374
JBrowse link
G Casp3 caspase 3 multiple interactions ISO 2,3-bis(4-hydroxyphenyl)-propionitrile promotes the reaction [Chlorodiphenyl (54% Chlorine) results in increased activity of CASP3 protein] CTD PMID:24216299 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Ccnd1 cyclin D1 multiple interactions ISO 2,3-bis(4-hydroxyphenyl)-propionitrile promotes the reaction [Chlorodiphenyl (54% Chlorine) results in decreased expression of CCND1 protein] CTD PMID:24216299 NCBI chr 1:218,090,750...218,100,447
Ensembl chr 1:218,090,750...218,100,325
JBrowse link
G Esr1 estrogen receptor 1 multiple interactions ISO 2,3-bis(4-hydroxyphenyl)-propionitrile binds to and results in increased activity of ESR1 protein; ESR1 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of BCL2 protein]; ESR1 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of PDCD4 protein]; ESR1 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of PTEN protein] CTD PMID:19264808 PMID:24425189 NCBI chr 1:41,192,029...41,594,799
Ensembl chr 1:41,192,824...41,594,796
JBrowse link
G Esr2 estrogen receptor 2 increases activity
increases expression
multiple interactions
ISO
EXP
2,3-bis(4-hydroxyphenyl)-propionitrile results in increased activity of ESR2 protein
2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of ESR2 protein; 2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of ESR2 protein alternative form
2,3-bis(4-hydroxyphenyl)-propionitrile binds to and results in increased activity of ESR2 protein; [2,3-bis(4-hydroxyphenyl)-propionitrile binds to and results in increased activity of ESR2 protein] inhibits the reaction [resveratrol results in decreased expression of PRL protein]
2,3-bis(4-hydroxyphenyl)-propionitrile results in increased phosphorylation of and results in increased localization of and results in increased activity of ESR2 protein; ESR2 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of BCL2 mRNA]; ESR2 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of PDCD4 mRNA]
2,3-bis(4-hydroxyphenyl)-propionitrile binds to and results in increased activity of ESR2 protein; [2,3-bis(4-hydroxyphenyl)-propionitrile binds to and results in increased activity of ESR2 protein] which results in increased secretion of Bicarbonates; ESR2 protein alternative form inhibits the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of ESR2 protein]
CTD PMID:18499763 PMID:19264808 PMID:20623183 PMID:22104698 PMID:22257560 PMID:25106122 PMID:27634370 NCBI chr 6:99,163,953...99,214,711
Ensembl chr 6:99,164,357...99,214,251
JBrowse link
G Mapk1 mitogen activated protein kinase 1 affects phosphorylation EXP 2,3-bis(4-hydroxyphenyl)-propionitrile affects the phosphorylation of MAPK1 protein CTD PMID:20870566 NCBI chr11:88,203,863...88,273,301
Ensembl chr11:88,211,599...88,273,254
JBrowse link
G Mapk3 mitogen activated protein kinase 3 affects phosphorylation EXP 2,3-bis(4-hydroxyphenyl)-propionitrile affects the phosphorylation of MAPK3 protein CTD PMID:20870566 NCBI chr 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
JBrowse link
G Mir21 microRNA 21 decreases expression ISO 2,3-bis(4-hydroxyphenyl)-propionitrile results in decreased expression of MIR21 mRNA CTD PMID:19264808 NCBI chr10:73,902,210...73,902,301
Ensembl chr10:73,902,210...73,902,301
JBrowse link
G Pdcd4 programmed cell death 4 increases expression
decreases expression
multiple interactions
ISO 2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of PDCD4 protein
2,3-bis(4-hydroxyphenyl)-propionitrile results in decreased expression of PDCD4 mRNA
ESR1 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of PDCD4 protein]; ESR2 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of PDCD4 mRNA]
CTD PMID:19264808 NCBI chr 1:274,616,625...274,648,204
Ensembl chr 1:274,625,224...274,648,204
JBrowse link
G Prl prolactin multiple interactions EXP [2,3-bis(4-hydroxyphenyl)-propionitrile binds to and results in increased activity of ESR2 protein] inhibits the reaction [resveratrol results in decreased expression of PRL protein] CTD PMID:22104698 NCBI chr17:39,814,236...39,824,299
Ensembl chr17:39,814,244...39,824,299
JBrowse link
G Pten phosphatase and tensin homolog increases expression
multiple interactions
ISO 2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of PTEN protein
ESR1 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of PTEN protein]
CTD PMID:19264808 NCBI chr 1:251,421,814...251,487,634
Ensembl chr 1:251,421,596...251,487,832
JBrowse link
G Ptger2 prostaglandin E receptor 2 decreases expression EXP 2,3-bis(4-hydroxyphenyl)-propionitrile results in decreased expression of PTGER2 mRNA CTD PMID:22257560 NCBI chr15:19,336,029...19,349,759
Ensembl chr15:19,338,175...19,350,210
JBrowse link
G Ptger4 prostaglandin E receptor 4 decreases expression EXP 2,3-bis(4-hydroxyphenyl)-propionitrile results in decreased expression of PTGER4 mRNA CTD PMID:22257560 NCBI chr 2:54,951,625...54,966,470
Ensembl chr 2:54,952,821...54,963,448
JBrowse link
G Ryr2 ryanodine receptor 2 increases phosphorylation EXP 2,3-bis(4-hydroxyphenyl)-propionitrile results in increased phosphorylation of RYR2 protein CTD PMID:25723814 NCBI chr17:65,533,998...65,955,606
Ensembl chr17:65,535,403...65,955,606
JBrowse link
G Sod2 superoxide dismutase 2 multiple interactions EXP
ISO
2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [[Oxygen deficiency co-treated with Oxygen] results in decreased activity of SOD2 protein]
2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [4,4',4''-(4-propyl-((1)H)-pyrazole-1,3,5-triyl) tris-phenol inhibits the reaction [Glucose results in decreased expression of SOD2 protein]]
CTD PMID:20962025 PMID:24465521 NCBI chr 1:47,914,757...47,921,587
Ensembl chr 1:47,914,759...47,921,587
JBrowse link
G Star steroidogenic acute regulatory protein increases expression ISO 2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of STAR protein CTD PMID:30206973 NCBI chr16:71,036,204...71,040,847
Ensembl chr16:71,036,204...71,040,847
JBrowse link

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  CHEBI ontology 19771
    chemical entity 19771
      group 19689
        pseudohalo group 2943
          cyano group 2943
            nitrile 2943
              2,3-bis(4-hydroxyphenyl)propionitrile 16
Path 2
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  CHEBI ontology 19771
    subatomic particle 19770
      composite particle 19770
        hadron 19770
          baryon 19770
            nucleon 19770
              atomic nucleus 19770
                atom 19770
                  main group element atom 19658
                    p-block element atom 19658
                      carbon group element atom 19574
                        carbon atom 19564
                          organic molecular entity 19564
                            one-carbon compound 17596
                              hydrogen cyanide 2947
                                cyanides 2947
                                  nitrile 2943
                                    2,3-bis(4-hydroxyphenyl)propionitrile 16
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