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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:neral
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Accession:CHEBI:29020 term browser browse the term
Definition:An enal that is 3,7-dimethyloctanal with unsaturation at positions C-2 and C-6. It has been isolated form the essential oils of plant species like lemon.
Synonyms:exact_synonym: (2Z)-3,7-dimethylocta-2,6-dienal
 related_synonym: Formula=C10H16O;   InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7-;   InChIKey=WTEVQBCEXWBHNA-YFHOEESVSA-N;   Lemonal;   SMILES=CC(C)=CCC\\C(C)=C/C=O;   cis-Citral;   citral B
 alt_id: CHEBI:10483;   CHEBI:25502
 xref: CAS:106-26-3;   HMDB:HMDB0035092;   KEGG:C09847;   KNApSAcK:C00003036;   LIPID_MAPS_instance:LMPR0102010006;   MetaCyc:CPD-9762;   PMID:15931590;   PMID:21809949;   PMID:23938144;   PMID:24066512;   Reaxys:1721872



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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 chr14:17,573,412...17,591,476
Ensembl chr14:17,573,412...17,591,480
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 chr17:65,759,778...65,808,013
Ensembl chr17:65,759,788...65,775,764
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 8:71,877,850...71,957,107
Ensembl chr 8:71,877,850...71,957,107
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 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478
JBrowse link
G Cd86 CD86 molecule increases expression ISO citral results in increased expression of CD86 protein CTD PMID:29540657 NCBI chr11:64,142,193...64,200,816
Ensembl chr11:64,163,828...64,200,818
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 1:79,622,077...79,643,782
Ensembl chr 1:79,622,077...79,643,782
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 chr14:17,181,030...17,183,075
Ensembl chr14:17,181,062...17,183,075
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 chr18:78,213,067...78,245,677
Ensembl chr18:78,202,342...78,258,535
Ensembl chr18:78,202,342...78,258,535
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 8:58,096,021...58,102,130
Ensembl chr 8:58,096,077...58,102,125
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 6:15,342,312...15,350,886
Ensembl chr 6:15,342,344...15,350,917
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 1:81,518,387...81,544,999
Ensembl chr 1:81,518,408...81,542,052
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 1:81,652,762...81,732,153
Ensembl chr 1:81,652,787...81,732,143
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 1:195,840,330...195,850,728
Ensembl chr 1:195,840,058...195,864,023
JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 multiple interactions ISO citral inhibits the reaction [CYP3A4 protein results in increased hydroxylation of Midazolam] CTD PMID:18385293 NCBI chr12:9,207,986...9,230,038
Ensembl chr12:9,015,383...9,285,008
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 chr12:16,806,222...16,846,428
Ensembl chr12:16,806,207...16,846,422
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 2:241,129,346...241,159,272
Ensembl chr 2:241,130,340...241,159,089
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 1:41,106,335...41,499,104
Ensembl chr 1:41,210,475...41,495,002
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 6:94,858,438...94,909,630
Ensembl chr 6:94,809,547...94,908,919
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 2:210,347,482...210,367,537
Ensembl chr 2:210,347,482...210,367,535
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 7:108,416,646...108,419,495
Ensembl chr 7:108,416,642...108,419,494
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 chr16:58,482,209...58,525,256
Ensembl chr16:58,482,505...58,525,661
JBrowse link
G Hmox1 heme oxygenase 1 increases expression ISO citral results in increased expression of HMOX1 mRNA CTD PMID:20491607 PMID:26244607 NCBI chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079
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 4:81,255,814...81,258,504
Ensembl chr 4:81,255,883...81,258,504
JBrowse link
G Icam1 intercellular adhesion molecule 1 increases expression ISO citral results in increased expression of ICAM1 protein CTD PMID:29540657 NCBI chr 8:19,553,063...19,565,438
Ensembl chr 8:19,553,645...19,565,438
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 7:53,903,339...53,907,375
Ensembl chr 7:53,903,337...53,907,375
JBrowse link
G Il18 interleukin 18 increases expression ISO citral results in increased expression of IL18 protein CTD PMID:23063874 NCBI chr 8:50,904,630...50,932,887
Ensembl chr 8:50,906,960...50,932,887
JBrowse link
G Il1a interleukin 1 alpha increases expression ISO citral results in increased expression of IL1A protein CTD PMID:23178550 NCBI chr 3:116,526,601...116,537,055
Ensembl chr 3:116,526,604...116,536,822
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 2:120,004,862...120,009,566
Ensembl chr 2:120,004,862...120,009,566
JBrowse link
G Il6 interleukin 6 increases secretion ISO citral results in increased secretion of IL6 protein CTD PMID:22245253 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178
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 7:110,912,499...110,923,851
Ensembl chr 7:110,912,499...110,923,851
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 3:119,499,039...119,502,911
Ensembl chr 3:119,498,810...119,502,995
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 chr12:20,951,058...20,999,198
Ensembl chr12:20,951,058...20,999,245
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 9:14,955,300...14,970,641
Ensembl chr 9:14,955,300...14,970,641
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 7:8,184,632...8,205,508
Ensembl chr 7:8,184,861...8,205,508
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 chr10:59,058,941...59,059,879
Ensembl chr10:59,052,828...59,060,676
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19812
    role 19763
      biological role 19763
        biochemical role 19380
          apoptosis inducer 13243
            neral 35
              citral + 35
Path 2
Term Annotations click to browse term
  CHEBI ontology 19812
    subatomic particle 19811
      composite particle 19811
        hadron 19811
          baryon 19811
            nucleon 19811
              atomic nucleus 19811
                atom 19811
                  main group element atom 19710
                    p-block element atom 19710
                      carbon group element atom 19631
                        carbon atom 19621
                          organic molecular entity 19621
                            organic group 18730
                              organic divalent group 18721
                                organodiyl group 18721
                                  carbonyl group 18670
                                    carbonyl compound 18670
                                      carboxylic acid 18367
                                        carboacyl group 17487
                                          univalent carboacyl group 17487
                                            formyl group 8799
                                              aldehyde 8799
                                                alpha,beta-unsaturated aldehyde 2896
                                                  enal 2896
                                                    neral 35
                                                      citral + 35
paths to the root