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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:vanillin
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Accession:CHEBI:18346 term browser browse the term
Definition:A member of the class of benzaldehydes carrying methoxy and hydroxy substituents at positions 3 and 4 respectively.
Synonyms:related_synonym: 3-methoxy-4-hydroxybenzaldehyde;   4-Hydroxy-3-methoxy-benzaldehyde;   4-Hydroxy-3-methoxybenzaldehyde;   4-formyl-2-methoxyphenol;   4-hydroxy-m-anisaldehyde;   Formula=C8H8O3;   InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3;   InChIKey=MWOOGOJBHIARFG-UHFFFAOYSA-N;   SMILES=[H]C(=O)C1=CC(OC)=C(O)C=C1;   Vanillaldehyde;   methylprotocatechuic aldehyde;   p-hydroxy-m-methoxybenzaldehyde;   p-vanillin;   vaniline;   vanillic aldehyde
 alt_id: CHEBI:15302;   CHEBI:1842;   CHEBI:20380;   CHEBI:48387
 xref: Beilstein:472792;   CAS:121-33-5;   FooDB:FDB000838;   Gmelin:3596;   HMDB:HMDB0012308;   KEGG:C00755;   KEGG:D00091;   KNApSAcK:C00002683;   KNApSAcK:C00029531
 xref_mesh: MESH:C100058
 xref: MetaCyc:VANILLIN;   PDBeChem:V55;   PMCID:PMC7790484;   PMCID:PMC8235570;   PMID:18479250;   PMID:19238838;   PMID:19812218;   PMID:21417387;   PMID:21542597;   PMID:21846089;   PMID:22308371;   PMID:29950589;   PMID:31661600;   PMID:33477040;   PMID:33938405;   PMID:34013088;   PMID:34035660;   UM-BBD_compID:c0193;   Wikipedia:Vanillin


show annotations for term's descendants           Sort by:
vanillin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Ache acetylcholinesterase multiple interactions ISO vanillin inhibits the reaction [[Fructose co-treated with Streptozocin] results in increased expression of ACHE protein] CTD PMID:33823243 NCBI chr 5:137,286,516...137,292,728
Ensembl chr 5:137,285,781...137,292,728 		JBrowse link
G Akr1c21 aldo-keto reductase family 1, member C21 increases expression ISO vanillin results in increased expression of AKR1C2 mRNA CTD PMID:20491607 NCBI chr13:4,624,074...4,636,542
Ensembl chr13:4,624,074...4,636,540 		JBrowse link
G Car1 carbonic anhydrase 1 decreases activity ISO vanillin results in decreased activity of CA1 protein CTD PMID:19231207 NCBI chr 3:14,831,274...14,873,425
Ensembl chr 3:14,831,276...14,873,428 		JBrowse link
G Car2 carbonic anhydrase 2 decreases activity ISO vanillin results in decreased activity of CA2 protein CTD PMID:19231207 NCBI chr 3:14,951,329...14,965,830
Ensembl chr 3:14,951,333...14,965,830 		JBrowse link
G Casp3 caspase 3 multiple interactions ISO vanillin inhibits the reaction [Cisplatin results in increased activity of CASP3 protein]; vanillin inhibits the reaction [Methotrexate results in increased activity of CASP3 protein] CTD PMID:29216766 NCBI chr 8:47,070,326...47,092,733
Ensembl chr 8:47,070,326...47,092,724 		JBrowse link
G Cat catalase multiple interactions EXP
ISO		 vanillin inhibits the reaction [potassium bromate results in increased activity of CAT protein]
vanillin inhibits the reaction [Cadmium Chloride results in decreased activity of CAT protein]
vanillin inhibits the reaction [[Fructose co-treated with Streptozocin] results in decreased activity of CAT protein]		 CTD PMID:26296324 PMID:33823243 PMID:37336463 NCBI chr 2:103,284,249...103,315,498
Ensembl chr 2:103,284,194...103,315,505 		JBrowse link
G Ccl2 C-C motif chemokine ligand 2 multiple interactions ISO vanillin inhibits the reaction [lipopolysaccharide, E coli O55-B5 results in increased secretion of CCL2 protein] CTD PMID:36416909 NCBI chr11:81,926,403...81,928,278
Ensembl chr11:81,926,397...81,928,279 		JBrowse link
G Ccn2 cellular communication network factor 2 decreases expression ISO vanillin results in decreased expression of CCN2 mRNA CTD PMID:17178418 NCBI chr10:24,471,340...24,474,581
Ensembl chr10:24,471,340...24,474,581 		JBrowse link
G Clk2 CDC-like kinase 2 increases expression ISO vanillin results in increased expression of CLK2 mRNA CTD PMID:17178418 NCBI chr 3:89,072,102...89,084,394
Ensembl chr 3:89,072,102...89,084,228 		JBrowse link
G Cst3 cystatin C multiple interactions ISO vanillin inhibits the reaction [Cisplatin results in increased expression of CST3 protein]; vanillin inhibits the reaction [Methotrexate results in increased expression of CST3 protein] CTD PMID:29216766 NCBI chr 2:148,713,642...148,717,432
Ensembl chr 2:148,713,642...148,717,612 		JBrowse link
G Cxcl15 C-X-C motif chemokine ligand 15 increases expression
multiple interactions		 ISO vanillin results in increased expression of CXCL8 mRNA
vanillin inhibits the reaction [lipopolysaccharide, E coli O55-B5 results in increased secretion of CXCL8 protein]		 CTD PMID:20491607 PMID:21920952 PMID:36416909 NCBI chr 5:90,942,393...90,950,926
Ensembl chr 5:90,942,393...90,950,926 		JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 increases expression ISO vanillin results in increased expression of CYP1A1 mRNA CTD PMID:20491607 NCBI chr 9:57,595,211...57,611,107
Ensembl chr 9:57,595,211...57,611,107 		JBrowse link
G Cyp2a5 cytochrome P450, family 2, subfamily a, polypeptide 5 decreases activity
multiple interactions		 ISO vanillin results in decreased activity of CYP2A6 protein
[[vanillin results in decreased activity of CYP2A6 protein] which results in decreased hydroxylation of 3-cyanocoumarin] which results in decreased chemical synthesis of 3-cyano-7-hydroxycoumarin; [vanillin results in decreased activity of CYP2A6 protein] which results in decreased hydroxylation of 3-cyanocoumarin		 CTD PMID:32496054 NCBI chr 7:26,534,764...26,542,689
Ensembl chr 7:26,534,730...26,542,973 		JBrowse link
G Ddit4 DNA-damage-inducible transcript 4 increases expression ISO vanillin results in increased expression of DDIT4 mRNA CTD PMID:17178418 NCBI chr10:59,785,497...59,787,592
Ensembl chr10:59,785,491...59,787,656 		JBrowse link
G Dnmt3b DNA methyltransferase 3B decreases expression ISO vanillin results in decreased expression of DNMT3B mRNA CTD PMID:17178418 NCBI chr 2:153,491,332...153,529,650
Ensembl chr 2:153,491,370...153,529,650 		JBrowse link
G Dusp6 dual specificity phosphatase 6 decreases expression ISO vanillin results in decreased expression of DUSP6 mRNA CTD PMID:17178418 NCBI chr10:99,098,676...99,103,351
Ensembl chr10:99,099,093...99,103,351 		JBrowse link
G Fasl Fas ligand multiple interactions ISO vanillin inhibits the reaction [Cisplatin results in increased expression of FASLG protein]; vanillin inhibits the reaction [Methotrexate results in increased expression of FASLG protein] CTD PMID:29216766 NCBI chr 1:161,608,260...161,616,064
Ensembl chr 1:161,608,258...161,616,064 		JBrowse link
G Fbp1 fructose bisphosphatase 1 affects binding ISO vanillin binds to FBP1 protein CTD PMID:33823243 NCBI chr13:63,012,567...63,036,112
Ensembl chr13:63,012,567...63,036,096 		JBrowse link
G Fgfr2 fibroblast growth factor receptor 2 decreases expression ISO vanillin results in decreased expression of FGFR2 mRNA CTD PMID:17178418 NCBI chr 7:129,764,181...129,868,538
Ensembl chr 7:129,764,181...132,725,079 		JBrowse link
G Fzd2 frizzled class receptor 2 decreases expression ISO vanillin results in decreased expression of FZD2 mRNA CTD PMID:17178418 NCBI chr11:102,495,257...102,498,884
Ensembl chr11:102,495,222...102,498,884 		JBrowse link
G G6pc1 glucose-6-phosphatase catalytic subunit 1 affects binding ISO vanillin binds to G6PC1 protein CTD PMID:33823243 NCBI chr11:101,258,542...101,268,729
Ensembl chr11:101,258,387...101,268,729 		JBrowse link
G G6pdx glucose-6-phosphate dehydrogenase X-linked multiple interactions ISO vanillin inhibits the reaction [Cadmium Chloride results in decreased activity of G6PD protein] CTD PMID:37336463 NCBI chr  X:73,453,089...73,472,486
Ensembl chr  X:73,453,089...73,472,800 		JBrowse link
G Gapdh glyceraldehyde-3-phosphate dehydrogenase multiple interactions ISO vanillin inhibits the reaction [Cadmium Chloride results in decreased activity of GAPDH protein] CTD PMID:37336463 NCBI chr 6:125,138,812...125,143,450
Ensembl chr 6:125,138,678...125,143,430 		JBrowse link
G Gclc glutamate-cysteine ligase, catalytic subunit increases expression ISO vanillin results in increased expression of GCLC mRNA CTD PMID:17178418 NCBI chr 9:77,661,817...77,701,771
Ensembl chr 9:77,661,817...77,701,767 		JBrowse link
G Gclm glutamate-cysteine ligase, modifier subunit increases expression ISO vanillin results in increased expression of GCLM mRNA CTD PMID:17178418 NCBI chr 3:122,039,206...122,060,864
Ensembl chr 3:122,039,206...122,064,381 		JBrowse link
G Glo1 glyoxalase 1 multiple interactions ISO vanillin inhibits the reaction [Cadmium Chloride results in decreased activity of GLO1 protein] CTD PMID:37336463 NCBI chr17:30,811,835...30,831,633
Ensembl chr17:30,803,910...30,845,845 		JBrowse link
G Gsr glutathione reductase multiple interactions ISO vanillin inhibits the reaction [Cadmium Chloride results in decreased activity of GSR protein] CTD PMID:37336463 NCBI chr 8:34,143,266...34,188,190
Ensembl chr 8:34,142,551...34,188,191 		JBrowse link
G Hmox1 heme oxygenase 1 increases expression ISO vanillin results in increased expression of HMOX1 mRNA CTD PMID:17178418 NCBI chr 8:75,820,246...75,827,221
Ensembl chr 8:75,820,249...75,827,217 		JBrowse link
G Hprt1 hypoxanthine phosphoribosyltransferase 1 decreases mutagenesis ISO vanillin results in decreased mutagenesis of HPRT1 gene CTD PMID:17178418 NCBI chr  X:52,076,955...52,110,537
Ensembl chr  X:52,077,014...52,110,536 		JBrowse link
G Hspa1b heat shock protein 1B increases expression ISO vanillin results in increased expression of HSPA1B mRNA CTD PMID:17178418 NCBI chr17:35,175,405...35,178,214
Ensembl chr17:35,175,412...35,178,214 		JBrowse link
G Il12b interleukin 12b multiple interactions ISO vanillin promotes the reaction [lipopolysaccharide, E coli O55-B5 results in increased secretion of IL12B protein] CTD PMID:36416909 NCBI chr11:44,290,890...44,305,504
Ensembl chr11:44,290,890...44,304,860 		JBrowse link
G Il18 interleukin 18 multiple interactions ISO vanillin inhibits the reaction [Cisplatin results in increased expression of IL18 protein]; vanillin inhibits the reaction [Methotrexate results in increased expression of IL18 protein] CTD PMID:29216766 NCBI chr 9:50,466,000...50,493,141
Ensembl chr 9:50,466,127...50,493,140 		JBrowse link
G Il1b interleukin 1 beta multiple interactions EXP vanillin inhibits the reaction [potassium bromate results in increased expression of IL1B mRNA] CTD PMID:26296324 NCBI chr 2:129,206,490...129,213,059
Ensembl chr 2:129,206,490...129,213,059 		JBrowse link
G Il6 interleukin 6 multiple interactions EXP vanillin inhibits the reaction [potassium bromate results in increased expression of IL6 mRNA] CTD PMID:26296324 NCBI chr 5:30,218,112...30,224,973
Ensembl chr 5:30,218,112...30,224,979 		JBrowse link
G Insig1 insulin induced gene 1 decreases expression ISO vanillin results in decreased expression of INSIG1 mRNA CTD PMID:17178418 NCBI chr 5:28,276,410...28,283,660
Ensembl chr 5:28,276,361...28,283,660 		JBrowse link
G Jund jun D proto-oncogene decreases expression ISO vanillin results in decreased expression of JUND mRNA CTD PMID:17178418 NCBI chr 8:71,150,389...71,153,265
Ensembl chr 8:71,151,599...71,153,265 		JBrowse link
G Lcn2 lipocalin 2 multiple interactions ISO vanillin inhibits the reaction [Cisplatin results in increased expression of LCN2 protein]; vanillin inhibits the reaction [Methotrexate results in increased expression of LCN2 protein] CTD PMID:29216766 NCBI chr 2:32,274,649...32,277,751
Ensembl chr 2:32,274,645...32,278,264 		JBrowse link
G Map2k2 mitogen-activated protein kinase kinase 2 decreases expression ISO vanillin results in decreased expression of MAP2K2 mRNA CTD PMID:17178418 NCBI chr10:80,941,749...80,960,531
Ensembl chr10:80,941,749...80,969,809 		JBrowse link
G Mark4 MAP/microtubule affinity regulating kinase 4 decreases expression ISO vanillin results in decreased expression of MARK4 mRNA CTD PMID:17178418 NCBI chr 7:19,159,027...19,193,255
Ensembl chr 7:19,158,700...19,192,746 		JBrowse link
G Mt1 metallothionein 1 multiple interactions EXP vanillin inhibits the reaction [potassium bromate results in increased expression of MT1 mRNA] CTD PMID:27074584 NCBI chr 8:94,905,214...94,906,955
Ensembl chr 8:94,905,710...94,906,955 		JBrowse link
G Mt2 metallothionein 2 increases expression
multiple interactions		 ISO
EXP		 vanillin results in increased expression of MT2A mRNA
vanillin inhibits the reaction [potassium bromate results in increased expression of MT2 mRNA]		 CTD PMID:20491607 PMID:27074584 NCBI chr 8:94,899,246...94,900,195
Ensembl chr 8:94,899,292...94,900,196 		JBrowse link
G Nos2 nitric oxide synthase 2, inducible multiple interactions ISO vanillin inhibits the reaction [Cisplatin results in increased expression of NOS2 protein]; vanillin inhibits the reaction [Methotrexate results in increased expression of NOS2 protein] CTD PMID:29216766 NCBI chr11:78,811,613...78,851,052
Ensembl chr11:78,811,613...78,851,080 		JBrowse link
G Ppp1r10 protein phosphatase 1, regulatory subunit 10 decreases expression ISO vanillin results in decreased expression of PPP1R10 mRNA CTD PMID:17178418 NCBI chr17:36,227,404...36,243,175
Ensembl chr17:36,227,326...36,243,175 		JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions EXP vanillin inhibits the reaction [Lipopolysaccharides results in increased expression of PTGS2 mRNA]; vanillin inhibits the reaction [potassium bromate results in increased expression of PTGS2 mRNA] CTD PMID:17465205 PMID:26296324 NCBI chr 1:149,975,851...149,983,978
Ensembl chr 1:149,975,782...149,983,978 		JBrowse link
G Pygl liver glycogen phosphorylase affects binding ISO vanillin binds to PYGL protein CTD PMID:33823243 NCBI chr12:70,237,589...70,274,457
Ensembl chr12:70,237,585...70,278,262 		JBrowse link
G Rela v-rel reticuloendotheliosis viral oncogene homolog A (avian) multiple interactions ISO vanillin inhibits the reaction [Cisplatin results in increased expression of RELA protein]; vanillin inhibits the reaction [Methotrexate results in increased expression of RELA protein] CTD PMID:29216766 NCBI chr19:5,686,993...5,698,162
Ensembl chr19:5,687,511...5,698,158 		JBrowse link
G Slc35d2 solute carrier family 35, member D2 decreases expression ISO vanillin results in decreased expression of SLC35D2 mRNA CTD PMID:17178418 NCBI chr13:64,244,122...64,277,195
Ensembl chr13:64,244,122...64,277,182 		JBrowse link
G Slc7a11 solute carrier family 7 (cationic amino acid transporter, y+ system), member 11 increases expression ISO vanillin results in increased expression of SLC7A11 mRNA CTD PMID:17178418 NCBI chr 3:50,319,385...50,403,947
Ensembl chr 3:49,846,975...50,398,063 		JBrowse link
G Tgfb1i1 transforming growth factor beta 1 induced transcript 1 decreases expression ISO vanillin results in decreased expression of TGFB1I1 mRNA CTD PMID:17178418 NCBI chr 7:127,845,963...127,852,884
Ensembl chr 7:127,845,984...127,854,871 		JBrowse link
G Tnf tumor necrosis factor multiple interactions EXP
ISO		 vanillin inhibits the reaction [potassium bromate results in increased expression of TNF mRNA]
vanillin inhibits the reaction [Cisplatin results in increased expression of TNF protein]; vanillin inhibits the reaction [Methotrexate results in increased expression of TNF protein]
vanillin inhibits the reaction [lipopolysaccharide, E coli O55-B5 results in increased secretion of TNF protein]		 CTD PMID:26296324 PMID:29216766 PMID:36416909 NCBI chr17:35,418,343...35,420,983
Ensembl chr17:35,418,357...35,420,983 		JBrowse link
G Trim16 tripartite motif-containing 16 increases expression ISO vanillin results in increased expression of TRIM16 mRNA CTD PMID:17178418 NCBI chr11:62,711,034...62,733,774
Ensembl chr11:62,711,057...62,741,634 		JBrowse link
G Trp53 transformation related protein 53 decreases expression ISO vanillin results in decreased expression of TP53 mRNA CTD PMID:17178418 NCBI chr11:69,471,174...69,482,699
Ensembl chr11:69,471,185...69,482,699 		JBrowse link
G Trpv3 transient receptor potential cation channel, subfamily V, member 3 increases activity EXP vanillin results in increased activity of TRPV3 protein CTD PMID:16617338 NCBI chr11:73,158,315...73,191,194
Ensembl chr11:73,158,214...73,191,189 		JBrowse link
G Ugp2 UDP-glucose pyrophosphorylase 2 increases expression ISO vanillin results in increased expression of UGP2 mRNA CTD PMID:17178418 NCBI chr11:21,271,126...21,321,267
Ensembl chr11:21,271,138...21,321,201 		JBrowse link
G Ugt1a10 UDP glycosyltransferase 1 family, polypeptide A10 increases glucuronidation ISO UGT1A10 protein results in increased glucuronidation of vanillin CTD PMID:15117964 NCBI chr 1:87,983,133...88,147,724
Ensembl chr 1:87,983,110...88,146,726 		JBrowse link
G Ugt1a2 UDP glucuronosyltransferase 1 family, polypeptide A2 increases glucuronidation ISO UGT1A3 protein results in increased glucuronidation of vanillin CTD PMID:15117964 NCBI chr 1:88,128,333...88,147,724
Ensembl chr 1:88,128,323...88,146,719 		JBrowse link
ethyl vanillin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Cyp2a5 cytochrome P450, family 2, subfamily a, polypeptide 5 multiple interactions
decreases activity		 ISO [[ethyl vanillin results in decreased activity of CYP2A6 protein] which results in decreased hydroxylation of 3-cyanocoumarin] which results in decreased chemical synthesis of 3-cyano-7-hydroxycoumarin; [ethyl vanillin results in decreased activity of CYP2A6 protein] which results in decreased hydroxylation of 3-cyanocoumarin CTD PMID:32496054 NCBI chr 7:26,534,764...26,542,689
Ensembl chr 7:26,534,730...26,542,973 		JBrowse link
G Or5d18 olfactory receptor family 5 subfamily D member 18 multiple interactions EXP [ethyl vanillin binds to and results in increased activity of OR5D18 protein] which results in increased transport of Calcium; ethyl vanillin binds to and results in increased activity of OR5D18 protein CTD PMID:15716417 NCBI chr 2:87,864,540...87,865,481
Ensembl chr 2:87,862,632...87,868,043 		JBrowse link
G Trpv3 transient receptor potential cation channel, subfamily V, member 3 increases activity EXP ethyl vanillin results in increased activity of TRPV3 protein CTD PMID:16617338 NCBI chr11:73,158,315...73,191,194
Ensembl chr11:73,158,214...73,191,189 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 22210
    role 22195
      chemical role 21440
        antioxidant 16420
          vanillin 57
            5-nitrovanillin + 0
            ethyl vanillin 3
            vanillin acetate 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 22210
    subatomic particle 22202
      composite particle 22202
        hadron 22202
          baryon 22202
            nucleon 22202
              atomic nucleus 22202
                atom 22202
                  main group element atom 22136
                    p-block element atom 22136
                      carbon group element atom 21936
                        carbon atom 21861
                          organic molecular entity 21861
                            heteroorganic entity 21517
                              organochalcogen compound 21005
                                organooxygen compound 20846
                                  carbon oxoacid 19634
                                    carboxylic acid 19630
                                      carboacyl group 18296
                                        univalent carboacyl group 18296
                                          formyl group 9127
                                            aldehyde 9127
                                              arenecarbaldehyde 146
                                                benzaldehydes 141
                                                  vanillin 57
                                                    5-nitrovanillin + 0
                                                    ethyl vanillin 3
                                                    vanillin acetate 0
paths to the root