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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 1:231,746,527...231,759,307
Ensembl chr 1:231,746,548...231,759,554
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 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921
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 chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
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 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626
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 chr20:7,149,177...7,159,727
Ensembl chr20:7,149,217...7,159,585
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 1:201,337,762...201,340,230
Ensembl chr 1:201,321,672...201,340,226
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 5:109,894,175...109,897,268
Ensembl chr 5:109,893,145...109,897,656
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 9:67,723,422...67,981,886
Ensembl chr 9:67,723,371...67,979,809
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 chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616
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 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863
JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 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 3:60,594,239...60,621,785
Ensembl chr 3:60,594,242...60,621,737
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 2:189,901,058...189,954,452
Ensembl chr 2:189,901,058...189,954,452
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 chr10:63,815,308...63,851,208
Ensembl chr10:63,815,308...63,851,210
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 chr19:35,295,633...35,310,528
Ensembl chr19:35,295,573...35,310,557
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 7:111,539,444...111,557,984
Ensembl chr 7:111,540,345...111,557,984
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 chr10:71,323,777...71,367,908
Ensembl chr10:71,323,777...71,367,908
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 1:81,196,532...81,212,848
Ensembl chr 1:81,196,532...81,212,847
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 chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 20089
    role 20042
      chemical role 19589
        antioxidant 15678
          dihydrolipoic acid 18
            (R)-dihydrolipoic acid + 0
            (S)-dihydrolipoic acid + 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 20089
    subatomic particle 20058
      composite particle 20058
        hadron 20088
          baryon 20088
            nucleon 20088
              atomic nucleus 20088
                atom 20058
                  main group element atom 19960
                    p-block element atom 19990
                      carbon group element atom 19916
                        carbon atom 19909
                          organic molecular entity 19909
                            organic group 18988
                              organic divalent group 18950
                                organodiyl group 18974
                                  carbonyl group 18903
                                    carbonyl compound 18925
                                      carboxylic acid 18597
                                        monocarboxylic acid 17843
                                          fatty acid 16480
                                            saturated fatty acid 16128
                                              straight-chain saturated fatty acid 15570
                                                octanoic acid 2725
                                                  dihydrolipoic acid 18
                                                    (R)-dihydrolipoic acid + 0
                                                    (S)-dihydrolipoic acid + 0
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