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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:dihydrolipoic acid
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Accession:CHEBI:18047 term browser browse the term
Definition:A thio-fatty acid that is reduced form of lipoic acid. A potent antioxidant shown to directly destroy superoxide, hydroperoxy and hydroxyl radicals; also has neuroprotective and anti-tumour effects.
Synonyms:exact_synonym: 6,8-disulfanyloctanoic acid
 related_synonym: 6,8-Dihydrothioctic acid;   6,8-bis-sulfanyloctanoic acid;   6,8-dimercapto-octanoic acid;   6,8-dimercaptooctanoic acid;   DHLA;   Dihydrothioctic acid;   Formula=C8H16O2S2;   InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10);   InChIKey=IZFHEQBZOYJLPK-UHFFFAOYSA-N;   SMILES=OC(=O)CCCCC(S)CCS;   dihydro-alpha-lipoic acid;   dihydro-lipoic acid
 alt_id: CHEBI:23752;   CHEBI:4569
 xref: Beilstein:1722777;   CAS:462-20-4;   DrugBank:DB03760;   Gmelin:675796;   HMDB:HMDB0012210;   KEGG:C02147
 xref_mesh: MESH:C015144
 xref: PMID:12127266;   PMID:1345759;   PMID:17403519;   PMID:18951944;   Reaxys:1722777;   Wikipedia:Dihydrolipoic_acid
 cyclic_relationship: is_conjugate_acid_of CHEBI:30316


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dihydrolipoic acid term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Acta2 actin alpha 2, smooth muscle multiple interactions EXP dihydrolipoic acid inhibits the reaction [TGFB1 protein results in increased expression of ACTA2 protein] CTD PMID:21251946 NCBI chr 1:252,537,614...252,550,394
Ensembl chr 1:252,537,615...252,550,394
JBrowse link
G Akt1 AKT serine/threonine kinase 1 multiple interactions EXP dihydrolipoic acid inhibits the reaction [PDGFB protein results in increased phosphorylation of AKT1 protein] CTD PMID:21251946 NCBI chr 6:137,218,398...137,239,970
Ensembl chr 6:137,218,376...137,236,258
JBrowse link
G Casp3 caspase 3 increases activity
multiple interactions
ISO dihydrolipoic acid results in increased activity of CASP3 protein
2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide inhibits the reaction [dihydrolipoic acid results in increased activity of CASP3 protein]
CTD PMID:21462292 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Casp9 caspase 9 increases activity
multiple interactions
ISO dihydrolipoic acid results in increased activity of CASP9 protein
2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide inhibits the reaction [dihydrolipoic acid results in increased activity of CASP9 protein]
CTD PMID:21462292 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 multiple interactions
increases expression
ISO 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide inhibits the reaction [dihydrolipoic acid results in increased expression of CDKN1A mRNA]; Acetylcysteine inhibits the reaction [dihydrolipoic acid results in increased expression of CDKN1A mRNA] CTD PMID:21462292 NCBI chr20:6,348,422...6,358,864
Ensembl chr20:6,351,458...6,358,864
JBrowse link
G Gstp1 glutathione S-transferase pi 1 multiple interactions
increases expression
EXP [dihydrolipoic acid promotes the reaction [JUN protein binds to GSTP1 enhancer]] which results in increased expression of GSTP1 mRNA; [dihydrolipoic acid promotes the reaction [NFE2L2 protein binds to GSTP1 enhancer]] which results in increased expression of GSTP1 mRNA; dihydrolipoic acid promotes the reaction [JUN protein binds to GSTP1 enhancer]; dihydrolipoic acid promotes the reaction [NFE2L2 protein binds to GSTP1 enhancer]; dihydrolipoic acid results in increased expression of and results in increased activity of GSTP1 protein
dihydrolipoic acid results in increased expression of GSTP1 mRNA
CTD PMID:20237067 NCBI chr 1:219,291,679...219,294,147
Ensembl chr 1:219,291,679...219,294,147
JBrowse link
G Jun Jun proto-oncogene, AP-1 transcription factor subunit multiple interactions
increases activity
increases expression
EXP [dihydrolipoic acid promotes the reaction [JUN protein binds to GSTP1 enhancer]] which results in increased expression of GSTP1 mRNA; dihydrolipoic acid promotes the reaction [JUN protein binds to GSTP1 enhancer]
dihydrolipoic acid results in increased activity of JUN protein
dihydrolipoic acid results in increased expression of JUN protein
CTD PMID:20237067 NCBI chr 5:114,011,184...114,014,277
Ensembl chr 5:114,011,189...114,014,277
JBrowse link
G Map2 microtubule-associated protein 2 multiple interactions ISO dihydrolipoic acid inhibits the reaction [NGF protein results in increased expression of MAP2 protein] CTD PMID:21462292 NCBI chr 9:73,204,753...73,462,965
Ensembl chr 9:73,319,710...73,462,972
JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions EXP dihydrolipoic acid inhibits the reaction [TGFB1 protein results in increased phosphorylation of MAPK1 protein] CTD PMID:21251946 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 multiple interactions EXP dihydrolipoic acid inhibits the reaction [TGFB1 protein results in increased phosphorylation of MAPK3 protein] CTD PMID:21251946 NCBI chr 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975
JBrowse link
G Nfe2l2 nuclear factor, erythroid 2-like 2 multiple interactions
increases expression
increases activity
EXP [dihydrolipoic acid promotes the reaction [NFE2L2 protein binds to GSTP1 enhancer]] which results in increased expression of GSTP1 mRNA; dihydrolipoic acid promotes the reaction [NFE2L2 protein binds to GSTP1 enhancer]
dihydrolipoic acid results in increased expression of NFE2L2 protein
dihydrolipoic acid results in increased activity of NFE2L2 protein
CTD PMID:20237067 NCBI chr 3:62,497,568...62,525,146
Ensembl chr 3:62,497,571...62,524,996
JBrowse link
G Ngf nerve growth factor multiple interactions ISO dihydrolipoic acid inhibits the reaction [NGF protein results in increased expression of MAP2 protein] CTD PMID:21462292 NCBI chr 2:204,886,158...204,939,523
Ensembl chr 2:204,886,202...204,940,453
JBrowse link
G Nos2 nitric oxide synthase 2 multiple interactions ISO dihydrolipoic acid inhibits the reaction [Lipopolysaccharides results in increased activity of NOS2 protein] CTD PMID:18838692 NCBI chr10:66,188,290...66,221,621
Ensembl chr10:66,189,786...66,313,190
JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 increases activity ISO dihydrolipoic acid results in increased activity of NQO1 protein CTD PMID:18838692 NCBI chr19:38,422,210...38,437,103
Ensembl chr19:38,422,164...38,437,180
JBrowse link
G Pdgfb platelet derived growth factor subunit B multiple interactions
decreases activity
EXP dihydrolipoic acid affects the reaction [PDGFB protein results in increased abundance of Reactive Oxygen Species]; dihydrolipoic acid inhibits the reaction [PDGFB protein results in increased phosphorylation of AKT1 protein]; dihydrolipoic acid inhibits the reaction [PDGFB protein results in increased phosphorylation of RPS6KB1 protein]
dihydrolipoic acid results in decreased activity of PDGFB protein
CTD PMID:21251946 NCBI chr 7:121,215,458...121,233,092
Ensembl chr 7:121,214,628...121,232,741
JBrowse link
G Rps6kb1 ribosomal protein S6 kinase B1 multiple interactions EXP dihydrolipoic acid inhibits the reaction [PDGFB protein results in increased phosphorylation of RPS6KB1 protein] CTD PMID:21251946 NCBI chr10:73,824,200...73,865,503
Ensembl chr10:73,824,202...73,865,364
JBrowse link
G Tgfb1 transforming growth factor, beta 1 multiple interactions EXP dihydrolipoic acid affects the reaction [TGFB1 protein results in increased abundance of Reactive Oxygen Species]; dihydrolipoic acid inhibits the reaction [TGFB1 protein results in increased expression of ACTA2 protein]; dihydrolipoic acid inhibits the reaction [TGFB1 protein results in increased phosphorylation of MAPK1 protein]; dihydrolipoic acid inhibits the reaction [TGFB1 protein results in increased phosphorylation of MAPK3 protein] CTD PMID:21251946 NCBI chr 1:82,480,875...82,497,196
Ensembl chr 1:82,480,195...82,497,199
JBrowse link
G Tp53 tumor protein p53 multiple interactions
increases expression
ISO 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide inhibits the reaction [dihydrolipoic acid results in increased expression of TRP53 mRNA]; Acetylcysteine inhibits the reaction [dihydrolipoic acid results in increased expression of TRP53 mRNA] CTD PMID:21462292 NCBI chr10:56,186,299...56,198,449
Ensembl chr10:56,187,020...56,198,449
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19841
    role 19792
      chemical role 19309
        antioxidant 14234
          dihydrolipoic acid 18
            (R)-dihydrolipoic acid + 0
            (S)-dihydrolipoic acid + 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19841
    subatomic particle 19839
      composite particle 19839
        hadron 19839
          baryon 19839
            nucleon 19839
              atomic nucleus 19839
                atom 19839
                  main group element atom 19732
                    p-block element atom 19732
                      carbon group element atom 19636
                        carbon atom 19625
                          organic molecular entity 19625
                            organic group 18537
                              organic divalent group 18528
                                organodiyl group 18528
                                  carbonyl group 18436
                                    carbonyl compound 18436
                                      carboxylic acid 18113
                                        monocarboxylic acid 17483
                                          fatty acid 16001
                                            saturated fatty acid 15974
                                              straight-chain saturated fatty acid 15424
                                                octanoic acid 2259
                                                  dihydrolipoic acid 18
                                                    (R)-dihydrolipoic acid + 0
                                                    (S)-dihydrolipoic acid + 0
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