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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:auranofin
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Accession:CHEBI:2922 term browser browse the term
Definition:An S-glycosyl compound consisting of 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-glucopyranose with the sufur atom coordinated to (triethylphosphoranylidene)gold. It is administered orally for the treatment of active progressive rheumatoid arthritis.
Synonyms:exact_synonym: (2,3,4,6-tetra-O-acetyl-1-thio-beta-D-glucopyranosato-kappaS(1))(triethylphosphine)gold
 related_synonym: (1-Thio-beta-D-glucopyranosato)(triethylphosphine)gold 2,3,4,6-tetraacetate;   2,3,4,6-Tetra-O-acetyl-1-thio-beta-D-glucopyranosato-S (triethylphosphine)gold;   Formula=C20H34AuO9PS;   InChI=1S/C14H20O9S.C6H15P.Au/c1-6(15)19-5-10-11(20-7(2)16)12(21-8(3)17)13(14(24)23-10)22-9(4)18;1-4-7(5-2)6-3;/h10-14,24H,5H2,1-4H3;4-6H2,1-3H3;/q;;+1/p-1/t10-,11-,12+,13-,14+;;/m1../s1;   InChIKey=AUJRCFUBUPVWSZ-XTZHGVARSA-M;   Ridaura;   SMILES=CC[P+](CC)(CC)[Au-]S[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O;   Triethylphosphine gold;   auranofina;   auranofine;   auranofinum
 xref: Beilstein:8187029;   CAS:34031-32-8;   DrugBank:DB00995;   Gmelin:112479;   Gmelin:294107;   KEGG:D00237
 xref_mesh: MESH:D001310
 xref: PMID:10796461;   PMID:11071118;   PMID:16036347;   PMID:17645497;   PMID:18409052;   PMID:18789312;   PMID:20127591;   PMID:22610278;   PMID:2656613;   PMID:6426843;   PMID:6426923;   PMID:9189058;   Patent:DE2051495;   Patent:US3635945;   Reaxys:11644694;   Reaxys:14401468;   Wikipedia:Auranofin



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auranofin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Alb albumin affects binding ISO Auranofin analog binds to ALB protein CTD PMID:16791640 NCBI chr 5:90,608,729...90,624,461
Ensembl chr 5:90,608,756...90,624,461
JBrowse link
G Bak1 BCL2-antagonist/killer 1 multiple interactions
increases response to substance
EXP [BAX co-treated with BAK1] results in increased susceptibility to Auranofin; BAK1 mutant form inhibits the reaction [Auranofin results in increased activity of CASP3 protein]
BAK1 results in increased susceptibility to Auranofin
CTD PMID:18789312 PMID:21172426 NCBI chr17:27,238,786...27,247,601
Ensembl chr17:27,238,784...27,247,983
JBrowse link
G Bax BCL2-associated X protein multiple interactions
increases response to substance
EXP [BAX co-treated with BAK1] results in increased susceptibility to Auranofin; BAX mutant form inhibits the reaction [Auranofin results in increased activity of CASP3 protein]
BAX results in increased susceptibility to Auranofin
CTD PMID:18789312 PMID:21172426 NCBI chr 7:45,111,124...45,116,332
Ensembl chr 7:45,111,121...45,116,322
JBrowse link
G Bcl2 B cell leukemia/lymphoma 2 multiple interactions ISO BCL2 protein inhibits the reaction [Auranofin results in increased activity of CASP3 protein] CTD PMID:18789312 NCBI chr 1:106,465,906...106,642,020
Ensembl chr 1:106,465,908...106,642,004
JBrowse link
G Casp3 caspase 3 multiple interactions
increases activity
ISO
EXP
Auranofin promotes the reaction [TNF protein results in increased activity of CASP3 protein]; Auranofin results in decreased expression of and results in increased cleavage of CASP3 protein; BCL2 protein inhibits the reaction [Auranofin results in increased activity of CASP3 protein]
BAK1 mutant form inhibits the reaction [Auranofin results in increased activity of CASP3 protein]; BAX mutant form inhibits the reaction [Auranofin results in increased activity of CASP3 protein]
CTD PMID:15159275 PMID:15191400 PMID:18789312 PMID:20542334 PMID:21699084 NCBI chr 8:47,070,326...47,092,733
Ensembl chr 8:47,070,326...47,092,724
JBrowse link
G Casp8 caspase 8 multiple interactions ISO Auranofin results in decreased expression of and results in increased cleavage of CASP8 protein CTD PMID:20542334 NCBI chr 1:58,834,553...58,886,663
Ensembl chr 1:58,834,533...58,886,662
JBrowse link
G Casp9 caspase 9 multiple interactions ISO Auranofin results in decreased expression of and results in increased cleavage of CASP9 protein CTD PMID:20542334 NCBI chr 4:141,520,923...141,543,289
Ensembl chr 4:141,520,923...141,543,287
JBrowse link
G Cdkn1a cyclin dependent kinase inhibitor 1A increases expression ISO Auranofin results in increased expression of CDKN1A protein CTD PMID:20542334 NCBI chr17:29,309,953...29,319,696
Ensembl chr17:29,309,950...29,319,701
JBrowse link
G Cebpe CCAAT/enhancer binding protein epsilon multiple interactions ISO [Auranofin co-treated with Tretinoin] results in increased expression of CEBPE protein CTD PMID:15159275 NCBI chr14:54,947,823...54,949,604
Ensembl chr14:54,947,817...54,949,631
JBrowse link
G Chuk conserved helix-loop-helix ubiquitous kinase multiple interactions EXP
ISO
Auranofin inhibits the reaction [[Ionomycin co-treated with Tetradecanoylphorbol Acetate] results in increased activity of CHUK protein]; Auranofin inhibits the reaction [Lipopolysaccharides results in increased activity of CHUK protein]
Auranofin inhibits the reaction [TNF protein results in increased activity of CHUK protein]
CTD PMID:10820281 NCBI chr19:44,061,773...44,095,940
Ensembl chr19:44,061,774...44,095,919
JBrowse link
G Dio1 deiodinase, iodothyronine, type I decreases activity ISO Auranofin results in decreased activity of DIO1 protein CTD PMID:34662569 NCBI chr 4:107,148,662...107,164,365
Ensembl chr 4:107,148,662...107,164,366
JBrowse link
G Gpx1 glutathione peroxidase 1 multiple interactions
increases expression
ISO [Peptidoglycan co-treated with Lipopolysaccharides] promotes the reaction [Auranofin results in increased expression of GPX1 protein]; Auranofin promotes the reaction [[Lipopolysaccharides co-treated with Peptidoglycan] results in increased expression of GPX1 protein] CTD PMID:21355852 NCBI chr 9:108,216,279...108,217,541
Ensembl chr 9:108,216,102...108,217,542
JBrowse link
G H2-Aa histocompatibility 2, class II antigen A, alpha increases response to substance ISO HLA-DQA1 gene polymorphism results in increased susceptibility to Auranofin CTD PMID:11436868 NCBI chr17:34,501,718...34,506,797
Ensembl chr17:34,501,718...34,506,797
JBrowse link
G H2-Eb1 histocompatibility 2, class II antigen E beta increases response to substance ISO HLA-DRB1 gene polymorphism results in increased susceptibility to Auranofin CTD PMID:11436868 NCBI chr17:34,524,841...34,535,648
Ensembl chr17:34,524,841...34,535,648
JBrowse link
G Hmox1 heme oxygenase 1 increases expression ISO
EXP
Auranofin results in increased expression of HMOX1 mRNA
Auranofin results in increased expression of HMOX1 mRNA; Auranofin results in increased expression of HMOX1 protein
CTD PMID:22008538 PMID:23942037 NCBI chr 8:75,820,246...75,827,221
Ensembl chr 8:75,820,249...75,827,217
JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO Auranofin inhibits the reaction [IL1B protein affects the localization of RELA protein]; Auranofin inhibits the reaction [IL1B protein results in increased expression of PTGS2 mRNA]; Auranofin inhibits the reaction [IL1B protein results in increased expression of PTGS2 protein] CTD PMID:10594346 NCBI chr 2:129,206,490...129,213,059
Ensembl chr 2:129,206,490...129,213,059
JBrowse link
G Il6 interleukin 6 multiple interactions ISO [Auranofin co-treated with IL6 protein] results in decreased phosphorylation of IL6ST protein; [Auranofin co-treated with IL6 protein] results in decreased phosphorylation of JAK2 protein; [Auranofin co-treated with IL6 protein] results in decreased phosphorylation of STAT3 protein CTD PMID:20542334 NCBI chr 5:30,218,112...30,224,973
Ensembl chr 5:30,218,112...30,224,979
JBrowse link
G Il6st interleukin 6 signal transducer multiple interactions ISO [Auranofin co-treated with IL6 protein] results in decreased phosphorylation of IL6ST protein CTD PMID:20542334 NCBI chr13:112,600,604...112,643,394
Ensembl chr13:112,600,604...112,646,620
JBrowse link
G Irak1 interleukin-1 receptor-associated kinase 1 multiple interactions EXP Auranofin inhibits the reaction [lipopolysaccharide A results in increased degradation of IRAK1 protein] CTD PMID:17034761 NCBI chr  X:73,057,520...73,067,527
Ensembl chr  X:73,057,520...73,067,524
JBrowse link
G Irf3 interferon regulatory factor 3 multiple interactions EXP Auranofin inhibits the reaction [lipopolysaccharide A results in increased activity of IRF3 protein]; Auranofin inhibits the reaction [lipopolysaccharide A results in increased phosphorylation of IRF3 protein]; Auranofin inhibits the reaction [TBK1 protein results in increased activity of IRF3 protein]; Auranofin inhibits the reaction [TICAM1 protein results in increased activity of IRF3 protein] CTD PMID:17034761 NCBI chr 7:44,647,072...44,652,272
Ensembl chr 7:44,647,072...44,652,272
JBrowse link
G Itgam integrin alpha M multiple interactions ISO [Auranofin co-treated with Tretinoin] results in increased expression of ITGAM protein CTD PMID:15159275 NCBI chr 7:127,661,812...127,717,663
Ensembl chr 7:127,661,812...127,717,663
JBrowse link
G Jak2 Janus kinase 2 multiple interactions ISO [Auranofin co-treated with IL6 protein] results in decreased phosphorylation of JAK2 protein CTD PMID:20542334 NCBI chr19:29,229,006...29,290,495
Ensembl chr19:29,229,228...29,290,480
JBrowse link
G Mcl1 myeloid cell leukemia sequence 1 multiple interactions
decreases expression
ISO [Auranofin co-treated with SN50 peptide] results in decreased expression of MCL1 protein
Auranofin results in decreased expression of MCL1 protein
CTD PMID:20542334 NCBI chr 3:95,564,017...95,583,553
Ensembl chr 3:95,566,099...95,570,487
JBrowse link
G Nfkbia nuclear factor of kappa light polypeptide gene enhancer in B cells inhibitor, alpha multiple interactions EXP Auranofin inhibits the reaction [Lipopolysaccharides results in increased degradation of NFKBIA protein] CTD PMID:10820281 NCBI chr12:55,536,194...55,539,432
Ensembl chr12:55,536,195...55,539,432
JBrowse link
G Nfkbib nuclear factor of kappa light polypeptide gene enhancer in B cells inhibitor, beta multiple interactions EXP Auranofin inhibits the reaction [Lipopolysaccharides results in increased degradation of NFKBIB protein] CTD PMID:10820281 NCBI chr 7:28,457,676...28,466,069
Ensembl chr 7:28,457,676...28,466,937
JBrowse link
G Parp1 poly (ADP-ribose) polymerase family, member 1 decreases activity
increases cleavage
ISO Auranofin results in decreased activity of PARP1 protein
Auranofin results in increased cleavage of PARP1 protein
CTD PMID:15159275 PMID:21370912 NCBI chr 1:180,396,456...180,428,564
Ensembl chr 1:180,396,489...180,428,819
JBrowse link
G Ppif peptidylprolyl isomerase F (cyclophilin F) increases oxidation
multiple interactions
ISO Auranofin results in increased oxidation of PPIF protein
Auranofin inhibits the reaction [[NADP co-treated with TXNRD1 protein] results in increased activity of PPIF protein]; Cyclosporine promotes the reaction [Auranofin results in increased oxidation of PPIF protein]
CTD PMID:26975474 NCBI chr14:25,693,998...25,700,892
Ensembl chr14:25,694,578...25,700,892
JBrowse link
G Prdx3 peroxiredoxin 3 increases oxidation
multiple interactions
EXP
ISO
Auranofin results in increased oxidation of PRDX3 protein
Auranofin promotes the reaction [[Lipopolysaccharides co-treated with Peptidoglycan] results in increased expression of PRDX3 protein]
Cyclosporine promotes the reaction [Auranofin results in increased oxidation of PRDX3 protein]
CTD PMID:18789312 PMID:21355852 PMID:26975474 NCBI chr19:60,852,504...60,862,976
Ensembl chr19:60,852,489...60,862,994
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions EXP
ISO
[lipopolysaccharide A co-treated with Auranofin] results in decreased expression of PTGS2 protein
Auranofin inhibits the reaction [IL1B protein results in increased expression of PTGS2 mRNA]; Auranofin inhibits the reaction [IL1B protein results in increased expression of PTGS2 protein]
CTD PMID:10594346 PMID:17034761 NCBI chr 1:149,975,851...149,983,978
Ensembl chr 1:149,975,782...149,983,978
JBrowse link
G Rb1 RB transcriptional corepressor 1 decreases phosphorylation ISO Auranofin results in decreased phosphorylation of RB1 protein CTD PMID:20542334 NCBI chr14:73,430,298...73,563,446
Ensembl chr14:73,421,113...73,563,262
JBrowse link
G Rbms3 RNA binding motif, single stranded interacting protein affects response to substance ISO RBMS3 protein affects the susceptibility to Auranofin CTD PMID:36414028 NCBI chr 9:116,401,814...117,869,900
Ensembl chr 9:116,401,814...117,701,749
JBrowse link
G Rela v-rel reticuloendotheliosis viral oncogene homolog A (avian) multiple interactions ISO Auranofin inhibits the reaction [IL1B protein affects the localization of RELA protein] CTD PMID:10594346 NCBI chr19:5,686,993...5,698,162
Ensembl chr19:5,687,511...5,698,158
JBrowse link
G Slc22a2 solute carrier family 22 (organic cation transporter), member 2 multiple interactions ISO Auranofin inhibits the reaction [SLC22A2 protein results in increased uptake of 4-(4-dimethylaminostyryl)-1-methylpyridinium] CTD PMID:21599003 NCBI chr17:12,803,076...12,847,376
Ensembl chr17:12,803,019...12,847,375
JBrowse link
G Stat3 signal transducer and activator of transcription 3 decreases expression
multiple interactions
ISO Auranofin results in decreased expression of STAT3 protein modified form
[Auranofin co-treated with IL6 protein] results in decreased phosphorylation of STAT3 protein
CTD PMID:20542334 NCBI chr11:100,777,632...100,830,447
Ensembl chr11:100,775,924...100,830,366
JBrowse link
G Tbk1 TANK-binding kinase 1 multiple interactions EXP Auranofin inhibits the reaction [TBK1 protein results in increased activity of IRF3 protein] CTD PMID:17034761 NCBI chr10:121,382,360...121,422,699
Ensembl chr10:121,382,360...121,422,692
JBrowse link
G Ticam1 TIR domain containing adaptor molecule 1 multiple interactions EXP Auranofin inhibits the reaction [TICAM1 protein results in increased activity of IRF3 protein] CTD PMID:17034761 NCBI chr17:56,576,462...56,583,767
Ensembl chr17:56,576,319...56,583,786
JBrowse link
G Tlr4 toll-like receptor 4 multiple interactions EXP Auranofin inhibits the reaction [lipopolysaccharide A promotes the reaction [TLR4 protein binds to TLR4 protein]] CTD PMID:17034761 NCBI chr 4:66,745,788...66,765,338
Ensembl chr 4:66,745,821...66,848,521
JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO
EXP
Auranofin inhibits the reaction [TNF protein results in increased activity of CHUK protein]; Auranofin promotes the reaction [TNF protein results in increased activity of CASP3 protein]
Auranofin inhibits the reaction [Lipopolysaccharides results in increased expression of TNF mRNA]
CTD PMID:10820281 PMID:18789312 NCBI chr17:35,418,343...35,420,983
Ensembl chr17:35,418,357...35,420,983
JBrowse link
G Txn1 thioredoxin 1 increases oxidation ISO Auranofin results in increased oxidation of TXN protein CTD PMID:26975474 NCBI chr 4:57,943,373...57,956,411
Ensembl chr 4:57,943,373...57,956,411
JBrowse link
G Txn2 thioredoxin 2 increases oxidation
multiple interactions
ISO Auranofin results in increased oxidation of TXN2 protein
Cyclosporine promotes the reaction [Auranofin results in increased oxidation of TXN2 protein]
CTD PMID:26975474 NCBI chr15:77,799,251...77,813,194
Ensembl chr15:77,799,247...77,813,206
JBrowse link
G Txnrd1 thioredoxin reductase 1 multiple interactions
increases expression
increases oxidation
decreases activity
ISO Auranofin inhibits the reaction [Sodium Selenite results in increased activity of TXNRD1 protein]; Auranofin promotes the reaction [Sodium Selenite results in increased expression of TXNRD1 mRNA]; potassium tellurate(IV) promotes the reaction [Auranofin results in increased oxidation of TXNRD1 protein]; Sodium Selenite promotes the reaction [Auranofin results in increased oxidation of TXNRD1 protein]
Auranofin results in increased expression of TXNRD1 mRNA
Auranofin results in decreased activity of TXNRD1 protein
Auranofin inhibits the reaction [[NADP co-treated with TXNRD1 protein] results in increased activity of PPIF protein]; Auranofin inhibits the reaction [[TXNRD1 protein co-treated with NADP] results in increased abundance of Superoxides]
CTD PMID:16510263 PMID:18405881 PMID:18789312 PMID:19486940 PMID:20457604 More... NCBI chr10:82,669,785...82,733,558
Ensembl chr10:82,669,785...82,733,546
JBrowse link
G Txnrd2 thioredoxin reductase 2 multiple interactions
decreases activity
ISO Auranofin inhibits the reaction [Sodium Selenite results in increased activity of TXNRD2 protein]; Auranofin promotes the reaction [Sodium Selenite results in decreased expression of TXNRD2 mRNA]
Auranofin results in decreased activity of TXNRD2 protein
CTD PMID:15458826 PMID:19486940 PMID:21172426 PMID:21355852 NCBI chr16:18,245,167...18,297,823
Ensembl chr16:18,245,134...18,297,823
JBrowse link

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  CHEBI ontology 22178
    role 22194
      biological role 22162
        immunomodulator 15681
          immunosuppressive agent 14566
            auranofin 42
Path 2
Term Annotations click to browse term
  CHEBI ontology 22178
    subatomic particle 22170
      composite particle 22170
        hadron 22201
          baryon 22170
            nucleon 22170
              atomic nucleus 22170
                atom 22170
                  main group element atom 22104
                    p-block element atom 22104
                      carbon group element atom 21904
                        carbon atom 21859
                          organic molecular entity 21830
                            heteroorganic entity 21482
                              organochalcogen compound 20966
                                organooxygen compound 20806
                                  carbohydrates and carbohydrate derivatives 16021
                                    carbohydrate 16041
                                      carbohydrate derivative 14790
                                        glycosyl compound 13148
                                          S-glycosyl compound 56
                                            auranofin 42
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