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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:citraconic acid
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Accession:CHEBI:17626 term browser browse the term
Definition:A dicarboxylic acid consisting of maleic acid having a methyl substituent at the 2-position.
Synonyms:exact_synonym: (2Z)-2-methylbut-2-enedioic acid
 related_synonym: (Z)-2-Methyl-2-butenedioic acid;   2-Methyl-2-butenedioic acid;   2-methylmaleic acid;   Citraconsaeure;   Formula=C5H6O4;   InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2-;   InChIKey=HNEGQIOMVPPMNR-IHWYPQMZSA-N;   Methyl-maleinsaeure;   Methylmaleic acid;   SMILES=C\\C(=C\\C(O)=O)C(O)=O;   alpha-methylmaleic acid;   cis-2-methylbutenedioic acid;   cis-Methylbutenedioic acid
 alt_id: CHEBI:11623;   CHEBI:1207;   CHEBI:19703;   CHEBI:19704
 xref: CAS:498-23-7;   DrugBank:DB04734;   HMDB:HMDB0000634;   KEGG:C02226
 xref_mesh: MESH:C073341
 xref: MetaCyc:2-METHYLMALEATE;   PMID:101016;   PMID:18852880;   PMID:955226;   Reaxys:1722679;   Wikipedia:Citraconic_acid
 cyclic_relationship: is_conjugate_acid_of CHEBI:30719


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citraconic acid term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Bach1 BTB domain and CNC homolog 1 affects localization ISO citraconic acid affects the localization of BACH1 protein CTD PMID:27277809 NCBI chr11:26,939,429...26,974,876
Ensembl chr11:40,425,664...40,461,277 		JBrowse link
G Foxm1 forkhead box M1 increases expression ISO citraconic acid results in increased expression of FOXM1 protein CTD PMID:28289076 NCBI chr 4:161,639,538...161,652,012
Ensembl chr 4:163,325,614...163,337,172 		JBrowse link
G Fth1 ferritin heavy chain 1 increases expression ISO citraconic acid results in increased expression of FTH1 protein CTD PMID:28289076 NCBI chr 1:216,052,037...216,054,325
Ensembl chr 1:216,051,998...216,055,214 		JBrowse link
G Ftl1 ferritin light chain 1 multiple interactions
increases expression 		ISO citraconic acid promotes the reaction [NFE2L2 protein results in increased expression of FTL protein]; NFE2L2 protein affects the reaction [citraconic acid results in increased expression of FTL protein] CTD PMID:28289076 NCBI chr 1:95,936,387...95,938,234
Ensembl chr  X:45,399,355...45,399,915
Ensembl chr 2:45,399,355...45,399,915
Ensembl chr 1:45,399,355...45,399,915 		JBrowse link
G Gclc glutamate-cysteine ligase, catalytic subunit increases expression EXP
ISO 		citraconic acid results in increased expression of GCLC protein
citraconic acid results in increased expression of GCLC mRNA 		CTD PMID:27277809 NCBI chr 8:87,510,251...87,548,896
Ensembl chr 8:87,510,463...87,548,893 		JBrowse link
G Gclm glutamate cysteine ligase, modifier subunit increases expression EXP
ISO 		citraconic acid results in increased expression of GCLM protein
citraconic acid results in increased expression of GCLM mRNA 		CTD PMID:27277809 NCBI chr 2:210,347,482...210,367,537
Ensembl chr 2:213,031,838...213,055,003 		JBrowse link
G Gsr glutathione-disulfide reductase increases expression ISO
EXP 		citraconic acid results in increased expression of GSR mRNA
citraconic acid results in increased expression of GSR protein 		CTD PMID:27277809 NCBI chr16:58,482,209...58,525,256
Ensembl chr16:65,185,574...65,228,394 		JBrowse link
G Hcar2 hydroxycarboxylic acid receptor 2 multiple interactions ISO citraconic acid binds to and results in increased activity of HCAR2 protein CTD PMID:18722346 NCBI chr12:32,726,252...32,728,238
Ensembl chr12:38,387,230...38,389,391 		JBrowse link
G Hmox1 heme oxygenase 1 increases expression EXP
ISO 		citraconic acid results in increased expression of HMOX1 mRNA; citraconic acid results in increased expression of HMOX1 protein CTD PMID:27277809 NCBI chr19:13,452,365...13,479,823
Ensembl chr19:13,472,884...13,479,818 		JBrowse link
G Mt-cyb mitochondrially encoded cytochrome b multiple interactions
increases expression 		ISO NFE2L2 protein affects the reaction [citraconic acid results in increased expression of CYTB mRNA] CTD PMID:27277809 NCBI chr MT:14,136...15,278
NCBI chr MT:14,136...15,278
NCBI chr MT:14,136...15,278
NCBI chr MT:14,136...15,278
NCBI chr MT:14,136...15,278
NCBI chr MT:14,136...15,278
NCBI chr MT:14,136...15,278
NCBI chr MT:14,136...15,278
NCBI chr MT:14,136...15,278
NCBI chr MT:14,136...15,278
NCBI chr MT:14,136...15,278
NCBI chr MT:14,136...15,278
NCBI chr MT:14,136...15,278
NCBI chr MT:14,136...15,278
Ensembl chr MT:14,124...15,266 		JBrowse link
G Mt-nd1 mitochondrially encoded NADH:ubiquinone oxidoreductase core subunit 1 increases expression
multiple interactions 		ISO citraconic acid results in increased expression of ND1 mRNA
NFE2L2 protein affects the reaction [citraconic acid results in increased expression of ND1 mRNA] 		CTD PMID:27277809 NCBI chr MT:2,740...3,694
NCBI chr MT:2,740...3,694
NCBI chr MT:2,740...3,694
Ensembl chr MT:2,729...3,685 		JBrowse link
G Mt-nd5 mitochondrially encoded NADH:ubiquinone oxidoreductase core subunit 5 increases expression
multiple interactions 		ISO citraconic acid results in increased expression of ND5 mRNA
NFE2L2 protein affects the reaction [citraconic acid results in increased expression of ND5 mRNA] 		CTD PMID:27277809 NCBI chr MT:11,736...13,565
NCBI chr MT:11,736...13,565
NCBI chr MT:11,736...13,565
NCBI chr MT:11,736...13,565
NCBI chr MT:11,736...13,565
NCBI chr MT:11,736...13,565
NCBI chr MT:11,736...13,565
NCBI chr MT:11,736...13,565
NCBI chr MT:11,736...13,565
NCBI chr MT:11,736...13,565
NCBI chr MT:11,736...13,565
NCBI chr MT:11,736...13,565
NCBI chr MT:11,736...13,565
Ensembl chr MT:11,721...13,553 		JBrowse link
G Mt-nd6 mitochondrially encoded NADH:ubiquinone oxidoreductase core subunit 6 multiple interactions
increases expression 		ISO NFE2L2 protein affects the reaction [citraconic acid results in increased expression of ND6 mRNA] CTD PMID:27277809 NCBI chr MT:13,543...14,061
NCBI chr MT:13,543...14,061
NCBI chr MT:13,543...14,061
NCBI chr MT:13,543...14,061
NCBI chr MT:13,543...14,061
NCBI chr MT:13,543...14,061
NCBI chr MT:13,543...14,061
NCBI chr MT:13,543...14,061
NCBI chr MT:13,543...14,061
NCBI chr MT:13,543...14,061
NCBI chr MT:13,543...14,061
NCBI chr MT:13,543...14,061
NCBI chr MT:13,543...14,061
NCBI chr MT:13,543...14,061
NCBI chr MT:13,543...14,061
NCBI chr MT:13,543...14,061
Ensembl chr MT:13,531...14,049 		JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 2 multiple interactions
affects localization 		ISO NFE2L2 protein affects the reaction [citraconic acid results in increased expression of CYTB mRNA]; NFE2L2 protein affects the reaction [citraconic acid results in increased expression of ND1 mRNA]; NFE2L2 protein affects the reaction [citraconic acid results in increased expression of ND5 mRNA]; NFE2L2 protein affects the reaction [citraconic acid results in increased expression of ND6 mRNA]; NFE2L2 protein affects the reaction [citraconic acid results in increased expression of POLRMT mRNA]
citraconic acid affects the localization of NFE2L2 protein
citraconic acid promotes the reaction [NFE2L2 protein results in increased expression of FTL protein]; NFE2L2 protein affects the reaction [citraconic acid results in increased expression of FTL protein] 		CTD PMID:27277809 PMID:28289076 NCBI chr 3:81,001,529...81,031,165
Ensembl chr 3:81,001,529...81,029,090 		JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 increases expression EXP citraconic acid results in increased expression of NQO1 mRNA; citraconic acid results in increased expression of NQO1 protein CTD PMID:27277809 NCBI chr19:52,205,374...52,220,267
Ensembl chr19:52,205,314...52,220,260 		JBrowse link
G Polrmt RNA polymerase mitochondrial increases expression
multiple interactions 		ISO citraconic acid results in increased expression of POLRMT mRNA
NFE2L2 protein affects the reaction [citraconic acid results in increased expression of POLRMT mRNA] 		CTD PMID:27277809 NCBI chr 7:10,610,149...10,620,411
Ensembl chr 7:10,610,198...10,621,205 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 20862
    role 20820
      biological role 20818
        biochemical role 20264
          metabolite 20245
            eukaryotic metabolite 19958
              plant metabolite 18270
                maleic acid 595
                  citraconic acid 16
Path 2
Term Annotations click to browse term
  CHEBI ontology 20862
    subatomic particle 20860
      composite particle 20860
        hadron 20860
          baryon 20860
            nucleon 20860
              atomic nucleus 20860
                atom 20860
                  main group element atom 20781
                    p-block element atom 20781
                      carbon group element atom 20715
                        carbon atom 20710
                          organic molecular entity 20710
                            heteroorganic entity 20219
                              organochalcogen compound 19904
                                organooxygen compound 19806
                                  carbonyl compound 19440
                                    dicarboxylic acids and O-substituted derivatives 12725
                                      dicarboxylic acid 12722
                                        C4-dicarboxylic acid 1372
                                          butenedioic acid 635
                                            maleic acid 595
                                              citraconic acid 16
paths to the root