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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:citral
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Accession:CHEBI:23316 term browser browse the term
Definition:An enal that consists of octa-2,6-dienal bearing methyl substituents at positions 3 and 7. A mixture of the two geometric isomers geranial and neral, it is the major constituent (75-85%) of oil of lemon grass, the volatile oil of Cymbopogon citratus, or of C. flexuosus. It also occurs in oils of verbena, lemon, and orange.
Synonyms:exact_synonym: 3,7-dimethylocta-2,6-dienal
 related_synonym: 3,7-dimethyl-2,6-octadienal;   Formula=C10H16O;   InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3;   InChIKey=WTEVQBCEXWBHNA-UHFFFAOYSA-N;   SMILES=C(=C(CCC=C(C)C)C)C=O;   cis,trans-Citral
 xref: Beilstein:1721871;   CAS:5392-40-5
 xref_mesh: MESH:C007076
 xref: PMID:20303242;   PMID:21174108;   PMID:21209212;   PMID:21316719;   PMID:21366054;   PMID:21510187;   PMID:21517071;   PMID:21525620;   PMID:21596542;   PMID:21713095;   PMID:21782918;   PMID:21826789;   Patent:US2661368;   Reaxys:970018;   Wikipedia:Citral


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citral term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Afp alpha-fetoprotein multiple interactions EXP citral inhibits the reaction [Diethylnitrosamine results in increased expression of AFP protein] CTD PMID:32302048 NCBI chr14:19,141,755...19,159,919
Ensembl chr14:19,141,755...19,159,923
JBrowse link
G Akr1c2 aldo-keto reductase family 1, member C2 increases expression
increases activity
ISO citral results in increased expression of AKR1C2 mRNA
citral results in increased activity of AKR1C2 promoter
CTD PMID:20491607, PMID:21195160 NCBI chr17:69,388,337...69,435,160
Ensembl chr17:69,388,335...69,404,341
JBrowse link
G Aldh1a2 aldehyde dehydrogenase 1 family, member A2 increases oxidation EXP ALDH1A2 protein results in increased oxidation of citral CTD PMID:23220587 NCBI chr 8:77,640,234...77,719,488
Ensembl chr 8:77,640,222...77,719,489
JBrowse link
G Cat catalase multiple interactions EXP citral inhibits the reaction [Diethylnitrosamine results in decreased expression of CAT protein] CTD PMID:32302048 NCBI chr 3:93,379,872...93,412,058
Ensembl chr 3:93,379,874...93,412,058
JBrowse link
G Cd86 CD86 molecule increases expression ISO citral results in increased expression of CD86 protein CTD PMID:29540657 NCBI chr11:67,060,305...67,117,990
Ensembl chr11:67,082,193...67,118,795
JBrowse link
G Ceacam20 CEA cell adhesion molecule 20 multiple interactions EXP citral inhibits the reaction [Diethylnitrosamine results in increased expression of CEACAM20 protein] CTD PMID:32302048 NCBI chr 1:80,880,856...80,912,082
Ensembl chr 1:80,880,856...80,912,082
JBrowse link
G Cxcl2 C-X-C motif chemokine ligand 2 increases expression ISO citral results in increased expression of CXCL2 protein CTD PMID:23178550 NCBI chr14:18,731,346...18,733,391
Ensembl chr14:18,731,378...18,733,391
JBrowse link
G Cyb5a cytochrome b5 type A multiple interactions EXP citral inhibits the reaction [Diethylnitrosamine results in increased expression of CYB5A protein] CTD PMID:32302048 NCBI chr18:81,694,818...81,726,821
Ensembl chr18:81,694,808...81,726,821
JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 multiple interactions ISO [[CYP1A1 protein co-treated with CYP1B1 protein co-treated with CYP2B6 protein co-treated with CYP2E1 protein co-treated with CYP3A5 protein] results in increased metabolism of geraniol] which results in increased chemical synthesis of citral; [[CYP1A1 protein co-treated with CYP1B1 protein co-treated with CYP2B6 protein co-treated with CYP2E1 protein co-treated with CYP3A5 protein] results in increased metabolism of geraniol] which results in increased chemical synthesis of citral metabolite; [CYP1A1 protein results in increased metabolism of geraniol] which results in increased chemical synthesis of citral CTD PMID:18824010 NCBI chr 8:62,472,087...62,478,122
Ensembl chr 8:62,472,095...62,478,147
JBrowse link
G Cyp1b1 cytochrome P450, family 1, subfamily b, polypeptide 1 multiple interactions ISO [[CYP1A1 protein co-treated with CYP1B1 protein co-treated with CYP2B6 protein co-treated with CYP2E1 protein co-treated with CYP3A5 protein] results in increased metabolism of geraniol] which results in increased chemical synthesis of citral; [[CYP1A1 protein co-treated with CYP1B1 protein co-treated with CYP2B6 protein co-treated with CYP2E1 protein co-treated with CYP3A5 protein] results in increased metabolism of geraniol] which results in increased chemical synthesis of citral metabolite CTD PMID:18824010 NCBI chr 6:2,308,179...2,316,739
Ensembl chr 6:2,307,808...2,316,722
JBrowse link
G Cyp2b1 cytochrome P450, family 2, subfamily b, polypeptide 1 decreases activity EXP citral results in decreased activity of CYP2B1 protein CTD PMID:9242356 NCBI chr 7:99,142,431...99,183,540
Ensembl chr 7:99,142,450...99,181,783
JBrowse link
G Cyp2b3 cytochrome P450, family 2, subfamily b, polypeptide 3 multiple interactions ISO [[CYP1A1 protein co-treated with CYP1B1 protein co-treated with CYP2B6 protein co-treated with CYP2E1 protein co-treated with CYP3A5 protein] results in increased metabolism of geraniol] which results in increased chemical synthesis of citral; [[CYP1A1 protein co-treated with CYP1B1 protein co-treated with CYP2B6 protein co-treated with CYP2E1 protein co-treated with CYP3A5 protein] results in increased metabolism of geraniol] which results in increased chemical synthesis of citral metabolite; [CYP2B6 protein results in increased metabolism of geraniol] which results in increased chemical synthesis of citral; citral inhibits the reaction [CYP2B6 protein results in increased hydrolysis of Bupropion] CTD PMID:18611395, PMID:18824010 NCBI chr 1:83,163,103...83,236,615
Ensembl chr 1:83,163,079...83,236,615
JBrowse link
G Cyp2e1 cytochrome P450, family 2, subfamily e, polypeptide 1 multiple interactions ISO [[CYP1A1 protein co-treated with CYP1B1 protein co-treated with CYP2B6 protein co-treated with CYP2E1 protein co-treated with CYP3A5 protein] results in increased metabolism of geraniol] which results in increased chemical synthesis of citral; [[CYP1A1 protein co-treated with CYP1B1 protein co-treated with CYP2B6 protein co-treated with CYP2E1 protein co-treated with CYP3A5 protein] results in increased metabolism of geraniol] which results in increased chemical synthesis of citral metabolite CTD PMID:18824010 NCBI chr 1:213,511,892...213,522,195
Ensembl chr 1:213,511,874...213,535,542
JBrowse link
G Cyp3a9 cytochrome P450, family 3, subfamily a, polypeptide 9 multiple interactions ISO [[CYP1A1 protein co-treated with CYP1B1 protein co-treated with CYP2B6 protein co-treated with CYP2E1 protein co-treated with CYP3A5 protein] results in increased metabolism of geraniol] which results in increased chemical synthesis of citral; [[CYP1A1 protein co-treated with CYP1B1 protein co-treated with CYP2B6 protein co-treated with CYP2E1 protein co-treated with CYP3A5 protein] results in increased metabolism of geraniol] which results in increased chemical synthesis of citral metabolite; [CYP3A5 protein results in increased metabolism of geraniol] which results in increased chemical synthesis of citral CTD PMID:18824010 NCBI chr12:19,074,288...19,114,491
Ensembl chr12:19,074,583...19,114,399
JBrowse link
G Dnajb4 DnaJ heat shock protein family (Hsp40) member B4 increases expression ISO citral results in increased expression of DNAJB4 mRNA CTD PMID:27965148 NCBI chr 2:257,394,692...257,425,344
Ensembl chr 2:257,394,818...257,425,242
JBrowse link
G Esr1 estrogen receptor 1 affects binding
multiple interactions
ISO citral binds to ESR1 protein
citral inhibits the reaction [Estradiol binds to ESR1 protein]
CTD PMID:12495555 NCBI chr 1:41,192,029...41,594,799
Ensembl chr 1:41,192,824...41,594,796
JBrowse link
G Esr2 estrogen receptor 2 affects binding
multiple interactions
ISO citral binds to ESR2 protein
citral inhibits the reaction [Estradiol binds to ESR2 protein]
CTD PMID:12495555 NCBI chr 6:99,163,953...99,214,711
Ensembl chr 6:99,164,357...99,214,251
JBrowse link
G Gclm glutamate cysteine ligase, modifier subunit increases expression ISO citral results in increased expression of GCLM mRNA CTD PMID:27965148 NCBI chr 2:225,827,504...225,847,876
Ensembl chr 2:225,827,504...225,847,874
JBrowse link
G Gpt glutamic--pyruvic transaminase multiple interactions EXP citral inhibits the reaction [Diethylnitrosamine results in increased expression of GPT protein] CTD PMID:32302048 NCBI chr 7:117,759,083...117,761,932
Ensembl chr 7:117,759,083...117,761,931
JBrowse link
G Gsr glutathione-disulfide reductase multiple interactions EXP citral inhibits the reaction [Diethylnitrosamine results in decreased expression of GSR protein] CTD PMID:32302048 NCBI chr16:62,197,617...62,239,987
Ensembl chr16:62,197,617...62,241,361
JBrowse link
G Hmox1 heme oxygenase 1 increases expression ISO citral results in increased expression of HMOX1 mRNA CTD PMID:20491607, PMID:26244607 NCBI chr19:14,508,634...14,515,455
Ensembl chr19:14,508,616...14,515,456
JBrowse link
G Hoxa1 homeobox A1 multiple interactions ISO citral inhibits the reaction [Vitamin A results in increased expression of HOXA1 mRNA] CTD PMID:23696197 NCBI chr 4:82,124,358...82,127,182
Ensembl chr 4:82,125,406...82,127,066
JBrowse link
G Icam1 intercellular adhesion molecule 1 increases expression ISO citral results in increased expression of ICAM1 protein CTD PMID:29540657 NCBI chr 8:22,035,287...22,047,049
Ensembl chr 8:22,035,256...22,047,059
JBrowse link
G Ifng interferon gamma multiple interactions ISO [citral co-treated with Ionomycin co-treated with Tetradecanoylphorbol Acetate] results in decreased expression of IFNG mRNA CTD PMID:29594315 NCBI chr 7:61,337,383...61,341,419
Ensembl chr 7:61,337,381...61,341,419
JBrowse link
G Il18 interleukin 18 increases expression ISO citral results in increased expression of IL18 protein CTD PMID:23063874 NCBI chr 8:55,009,666...55,016,286
Ensembl chr 8:54,993,859...55,016,299
JBrowse link
G Il1a interleukin 1 alpha increases expression ISO citral results in increased expression of IL1A protein CTD PMID:23178550 NCBI chr 3:121,824,712...121,836,122
Ensembl chr 3:121,825,412...121,836,086
JBrowse link
G Il2 interleukin 2 increases secretion
multiple interactions
ISO citral results in increased secretion of IL2 protein
[citral co-treated with Ionomycin co-treated with Tetradecanoylphorbol Acetate] results in decreased expression of IL2 mRNA
CTD PMID:22245253, PMID:29594315 NCBI chr 2:123,847,150...123,851,854
Ensembl chr 2:123,847,150...123,851,854
JBrowse link
G Il6 interleukin 6 increases secretion ISO citral results in increased secretion of IL6 protein CTD PMID:22245253 NCBI chr 4:3,043,231...3,047,807
Ensembl chr 4:3,043,231...3,047,807
JBrowse link
G Maff MAF bZIP transcription factor F increases expression ISO citral results in increased expression of MAFF mRNA CTD PMID:20491607 NCBI chr 7:120,580,743...120,592,095
Ensembl chr 7:120,580,743...120,592,095
JBrowse link
G Pcna proliferating cell nuclear antigen multiple interactions EXP citral inhibits the reaction [Diethylnitrosamine results in increased expression of PCNA protein] CTD PMID:32302048 NCBI chr 3:124,880,698...124,884,570
Ensembl chr 3:124,880,698...124,884,570
JBrowse link
G Por cytochrome p450 oxidoreductase multiple interactions EXP citral inhibits the reaction [Diethylnitrosamine results in increased expression of POR protein] CTD PMID:32302048 NCBI chr12:23,998,411...24,017,063
Ensembl chr12:23,998,411...24,046,814
JBrowse link
G Vegfa vascular endothelial growth factor A increases expression ISO citral results in increased expression of VEGFA protein CTD PMID:25617811 NCBI chr 9:17,340,341...17,355,681
Ensembl chr 9:17,340,341...17,355,681
JBrowse link
citral dimethyl acetal term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Gna15 G protein subunit alpha 15 increases response to substance
multiple interactions
ISO GNA15 protein results in increased susceptibility to citral dimethyl acetal
[GNA15 protein results in increased susceptibility to citral dimethyl acetal] which results in increased activity of OLFR43 protein
CTD PMID:15598656 NCBI chr 7:11,054,249...11,075,152
Ensembl chr 7:11,054,333...11,077,251
JBrowse link
G Olr1513 olfactory receptor 1513 multiple interactions ISO [GNA15 protein results in increased susceptibility to citral dimethyl acetal] which results in increased activity of OLFR43 protein CTD PMID:15598656 NCBI chr10:61,033,113...61,034,051
Ensembl chr10:61,033,113...61,034,051
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19816
    role 19764
      application 19426
        fragrance 854
          citral 34
            citral dimethyl acetal 2
Path 2
Term Annotations click to browse term
  CHEBI ontology 19816
    subatomic particle 19814
      composite particle 19814
        hadron 19814
          baryon 19814
            nucleon 19814
              atomic nucleus 19814
                atom 19814
                  main group element atom 19702
                    p-block element atom 19702
                      carbon group element atom 19608
                        carbon atom 19597
                          organic molecular entity 19597
                            organic group 18537
                              organic divalent group 18530
                                organodiyl group 18530
                                  carbonyl group 18436
                                    carbonyl compound 18436
                                      carboxylic acid 18114
                                        carboacyl group 17372
                                          univalent carboacyl group 17372
                                            formyl group 7851
                                              aldehyde 7851
                                                alpha,beta-unsaturated aldehyde 1300
                                                  enal 1300
                                                    polyprenal 34
                                                      geranial 34
                                                        citral 34
                                                          citral dimethyl acetal 2
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.