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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 chr14:17,607,397...17,622,814
Ensembl chr14:17,607,381...17,622,836
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 chr20:5,100,480...5,109,669
Ensembl chr20:5,100,480...5,109,264
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 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368
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 chr13:22,689,783...22,853,920 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 chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
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 9:60,263,863...60,312,542
Ensembl chr 9:60,264,075...60,312,542
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 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626
JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A increases expression ISO Auranofin results in increased expression of CDKN1A protein CTD PMID:20542334 NCBI chr20:7,149,177...7,159,727
Ensembl chr20:7,149,217...7,159,585
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 chr15:28,169,885...28,171,283
Ensembl chr15:28,169,704...28,171,814
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 1:242,959,539...242,995,066
Ensembl chr 1:242,959,760...242,995,065
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 8:109,026,905...109,028,031
Ensembl chr 8:109,026,905...109,028,024
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 chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079
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 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415
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 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178
JBrowse link
G Il6st interleukin 6 cytokine family signal transducer multiple interactions ISO [Auranofin co-treated with IL6 protein] results in decreased phosphorylation of IL6ST protein CTD PMID:20542334 NCBI chr 2:44,065,979...44,106,255
Ensembl chr 2:44,066,130...44,109,936
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:151,768,621...151,778,521
Ensembl chr  X:151,768,777...151,778,521
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 1:95,479,966...95,484,926
Ensembl chr 1:95,479,821...95,484,935
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 1:182,659,047...182,709,495
Ensembl chr 1:182,659,000...182,709,503
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 1:226,995,334...227,054,381
Ensembl chr 1:226,995,334...227,054,189
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 2:183,219,137...183,235,676
Ensembl chr 2:183,219,220...183,222,303
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 6:72,858,713...72,861,941
Ensembl chr 6:72,858,712...72,861,941
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 1:84,046,292...84,053,862
Ensembl chr 1:84,046,295...84,053,862
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 chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404
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 chr16:1,257,197...1,263,919
Ensembl chr16:1,257,106...1,263,913
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 1:260,001,642...260,014,064
Ensembl chr 1:260,001,637...260,014,111
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 chr13:62,164,080...62,169,770
Ensembl chr13:62,163,932...62,172,188
JBrowse link
G Rb1 RB transcriptional corepressor 1 decreases phosphorylation ISO Auranofin results in decreased phosphorylation of RB1 protein CTD PMID:20542334 NCBI chr15:48,371,295...48,502,473
Ensembl chr15:48,371,296...48,502,302
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 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484
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 chr20:4,575,134...4,579,727
Ensembl chr20:4,575,134...4,579,744
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 chr20:4,548,664...4,558,237
Ensembl chr20:4,548,666...4,558,258
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 1:48,121,061...48,163,268
Ensembl chr 1:48,121,061...48,163,268
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 chr10:85,811,206...85,863,057
Ensembl chr10:85,811,218...85,863,057
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 7:57,077,830...57,110,868
Ensembl chr 7:57,077,830...57,110,892
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 9:1,102,559...1,115,573 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 5:80,145,867...80,159,501
Ensembl chr 5:80,145,826...80,159,628
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 chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link
G Txn1 thioredoxin 1 increases oxidation ISO Auranofin results in increased oxidation of TXN protein CTD PMID:26975474 NCBI chr 5:72,712,334...72,724,564
Ensembl chr 5:72,711,933...72,724,629
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 7:109,496,772...109,510,378
Ensembl chr 7:109,496,761...109,510,359
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 More... NCBI chr 7:20,830,042...20,914,990
Ensembl chr 7:20,830,045...20,907,863
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 chr11:82,519,996...82,568,156
Ensembl chr11:82,519,999...82,568,156
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19800
    role 19751
      biological role 19751
        immunomodulator 14908
          immunosuppressive agent 13741
            auranofin 40
Path 2
Term Annotations click to browse term
  CHEBI ontology 19800
    subatomic particle 19799
      composite particle 19799
        hadron 19799
          baryon 19799
            nucleon 19799
              atomic nucleus 19799
                atom 19799
                  main group element atom 19698
                    p-block element atom 19698
                      carbon group element atom 19619
                        carbon atom 19609
                          organic molecular entity 19609
                            heteroorganic entity 19278
                              organochalcogen compound 19052
                                organooxygen compound 18998
                                  carbohydrates and carbohydrate derivatives 12342
                                    carbohydrate 12342
                                      carbohydrate derivative 11946
                                        glycosyl compound 10983
                                          S-glycosyl compound 57
                                            auranofin 40
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