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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 chr14:19,176,275...19,191,793
Ensembl chr14:19,176,277...19,191,863
JBrowse link
G Bak1 BCL2-antagonist/killer 1 multiple interactions
increases response to substance
ISO [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 chr20:5,609,620...5,618,899
Ensembl chr20:5,609,625...5,618,260
JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions
increases response to substance
ISO [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 1:101,451,801...101,457,207
Ensembl chr 1:101,451,802...101,457,207
JBrowse link
G Bcl2 BCL2, apoptosis regulator multiple interactions ISO BCL2 protein inhibits the reaction [Auranofin results in increased activity of CASP3 protein] CTD PMID:18789312 NCBI chr13:26,605,426...26,769,374
Ensembl chr13:26,605,426...26,769,374
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 chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
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 9:65,614,142...65,662,624
Ensembl chr 9:65,614,142...65,662,106
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 5:160,356,211...160,373,774
Ensembl chr 5:160,355,833...160,373,778
JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A increases expression ISO Auranofin results in increased expression of CDKN1A protein CTD PMID:20542334 NCBI chr20:6,348,422...6,358,864
Ensembl chr20:6,351,458...6,358,864
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 chr15:33,356,119...33,357,517
Ensembl chr15:33,355,947...33,358,138
JBrowse link
G Chuk component of inhibitor of nuclear factor kappa B kinase complex multiple interactions 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 chr 1:263,848,829...263,884,354
Ensembl chr 1:263,848,884...263,885,169
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 8:117,117,430...117,118,528
Ensembl chr 8:117,117,430...117,118,522
JBrowse link
G Hmox1 heme oxygenase 1 increases expression ISO 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 chr19:14,508,634...14,515,455
Ensembl chr19:14,508,616...14,515,456
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 3:121,876,256...121,882,637
Ensembl chr 3:121,876,263...121,882,726
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 4:3,043,231...3,047,807
Ensembl chr 4:3,043,231...3,047,807
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 chr 2:44,279,199...44,319,427
Ensembl chr 2:44,289,393...44,314,944
JBrowse link
G Irak1 interleukin-1 receptor-associated kinase 1 multiple interactions ISO Auranofin inhibits the reaction [lipopolysaccharide A results in increased degradation of IRAK1 protein] CTD PMID:17034761 NCBI chr  X:156,716,469...156,726,367
Ensembl chr  X:156,716,604...156,725,977
JBrowse link
G Irf3 interferon regulatory factor 3 multiple interactions ISO 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 1:100,992,244...100,997,202
Ensembl chr 1:100,992,405...100,997,198
JBrowse link
G Itgam integrin subunit alpha M multiple interactions ISO [Auranofin co-treated with Tretinoin] results in increased expression of ITGAM protein CTD PMID:15159275 NCBI chr 1:199,495,312...199,545,738
Ensembl chr 1:199,495,298...199,623,960
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 chr 1:247,398,667...247,457,521
Ensembl chr 1:247,398,598...247,458,509
JBrowse link
G Mcl1 MCL1 apoptosis regulator, BCL2 family member 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 2:197,786,212...197,788,992 JBrowse link
G Nfkbia NFKB inhibitor alpha multiple interactions ISO Auranofin inhibits the reaction [Lipopolysaccharides results in increased degradation of NFKBIA protein] CTD PMID:10820281 NCBI chr 6:76,267,227...76,270,457
Ensembl chr 6:76,267,228...76,270,457
JBrowse link
G Nfkbib NFKB inhibitor beta multiple interactions ISO Auranofin inhibits the reaction [Lipopolysaccharides results in increased degradation of NFKBIB protein] CTD PMID:10820281 NCBI chr 1:86,941,073...86,948,845
Ensembl chr 1:86,941,074...86,948,845
JBrowse link
G Parp1 poly (ADP-ribose) polymerase 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 chr13:98,857,255...98,889,444
Ensembl chr13:98,857,177...98,889,716
JBrowse link
G Ppif peptidylprolyl isomerase F increases oxidation
multiple interactions
ISO
EXP
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 chr16:1,979,191...1,985,912
Ensembl chr16:1,979,191...1,985,908
JBrowse link
G Prdx3 peroxiredoxin 3 increases oxidation
multiple interactions
ISO
EXP
Auranofin results in increased oxidation of PRDX3 protein
Cyclosporine promotes the reaction [Auranofin results in increased oxidation of PRDX3 protein]
Auranofin promotes the reaction [[Lipopolysaccharides co-treated with Peptidoglycan] results in increased expression of PRDX3 protein]
CTD PMID:18789312, PMID:21355852, PMID:26975474 NCBI chr 1:282,238,774...282,251,193
Ensembl chr 1:282,238,773...282,251,257
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions 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 chr13:67,351,230...67,356,920
Ensembl chr13:67,351,087...67,359,335
JBrowse link
G Rb1 RB transcriptional corepressor 1 decreases phosphorylation ISO Auranofin results in decreased phosphorylation of RB1 protein CTD PMID:20542334 NCBI chr15:55,081,582...55,209,060
Ensembl chr15:55,083,140...55,209,342
JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions ISO Auranofin inhibits the reaction [IL1B protein affects the localization of RELA protein] CTD PMID:10594346 NCBI chr 1:220,992,770...221,003,249
Ensembl chr 1:220,992,770...221,003,249
JBrowse link
G RT1-Ba RT1 class II, locus Ba increases response to substance ISO HLA-DQA1 gene polymorphism results in increased susceptibility to Auranofin CTD PMID:11436868 NCBI chr20:4,066,133...4,070,726
Ensembl chr20:4,066,132...4,070,721
JBrowse link
G RT1-Db1 RT1 class II, locus Db1 increases response to substance ISO HLA-DRB1 gene polymorphism results in increased susceptibility to Auranofin CTD PMID:11436868 NCBI chr20:4,087,621...4,097,190
Ensembl chr20:4,087,618...4,097,190
JBrowse link
G Slc22a2 solute carrier family 22 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 chr 1:48,318,025...48,360,219
Ensembl chr 1:48,317,995...48,360,261
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 chr10:88,790,401...88,842,263
Ensembl chr10:88,790,408...88,842,233
JBrowse link
G Tbk1 TANK-binding kinase 1 multiple interactions ISO Auranofin inhibits the reaction [TBK1 protein results in increased activity of IRF3 protein] CTD PMID:17034761 NCBI chr 7:63,655,247...63,687,978
Ensembl chr 7:63,655,247...63,687,978
JBrowse link
G Ticam1 toll-like receptor adaptor molecule 1 multiple interactions ISO Auranofin inhibits the reaction [TICAM1 protein results in increased activity of IRF3 protein] CTD PMID:17034761 NCBI chr 9:10,780,185...10,790,280 JBrowse link
G Tlr4 toll-like receptor 4 multiple interactions ISO Auranofin inhibits the reaction [lipopolysaccharide A promotes the reaction [TLR4 protein binds to TLR4 protein]] CTD PMID:17034761 NCBI chr 5:82,587,424...82,601,056
Ensembl chr 5:82,587,420...82,601,052
JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO 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 chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link
G Txn1 thioredoxin 1 increases oxidation ISO Auranofin results in increased oxidation of TXN protein CTD PMID:26975474 NCBI chr 5:75,049,735...75,057,731
Ensembl chr 5:75,049,747...75,057,752
JBrowse link
G Txn2 thioredoxin 2 increases oxidation
multiple interactions
ISO
EXP
Auranofin results in increased oxidation of TXN2 protein
Cyclosporine promotes the reaction [Auranofin results in increased oxidation of TXN2 protein]
CTD PMID:26975474 NCBI chr 7:119,144,350...119,158,173
Ensembl chr 7:119,144,351...119,158,201
JBrowse link
G Txnrd1 thioredoxin reductase 1 multiple interactions
decreases activity
increases oxidation
increases expression
ISO
EXP
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 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]
Auranofin results in decreased activity of TXNRD1 protein
Auranofin results in increased expression of TXNRD1 mRNA
CTD PMID:16510263, PMID:18405881, PMID:18789312, PMID:19486940, PMID:20457604, PMID:21172426, PMID:26975474 NCBI chr 7:26,946,124...26,984,400
Ensembl chr 7:26,946,125...26,984,400
JBrowse link
G Txnrd2 thioredoxin reductase 2 multiple interactions
decreases activity
ISO
EXP
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 chr11:86,667,994...86,716,063
Ensembl chr11:86,667,997...86,716,254
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19787
    role 19734
      biological role 19734
        immunomodulator 13691
          immunosuppressive agent 11937
            auranofin 40
Path 2
Term Annotations click to browse term
  CHEBI ontology 19787
    subatomic particle 19784
      composite particle 19784
        hadron 19784
          baryon 19784
            nucleon 19784
              atomic nucleus 19784
                atom 19784
                  main group element atom 19672
                    p-block element atom 19672
                      carbon group element atom 19574
                        carbon atom 19563
                          organic molecular entity 19563
                            heteroorganic entity 19148
                              organochalcogen compound 18856
                                organooxygen compound 18778
                                  carbohydrates and carbohydrate derivatives 12180
                                    carbohydrate 12180
                                      carbohydrate derivative 11804
                                        glycosyl compound 10848
                                          S-glycosyl compound 56
                                            auranofin 40
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.