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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:zingerone
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Accession:CHEBI:68657 term browser browse the term
Definition:A methyl ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at positions 3 and 4 by methoxy and hydroxy groups respectively. The major pungent component in ginger.
Synonyms:exact_synonym: 4-(4-hydroxy-3-methoxyphenyl)butan-2-one
 related_synonym: (0)-Paradol;   (4-Hydroxy-3-methoxyphenyl)ethyl methyl ketone;   2-(4-Hydroxy-3-methoxyphenyl)ethyl methyl ketone;   3-Methoxy-4-hydroxybenzylacetone;   4-(3-Methoxy-4-hydroxyphenyl)-2-butanone;   4-(3-methoxy-4-hydroxyphenyl)butan-2-one;   4-(4-Hydroxy-3-methoxyphenyl)-2-butanone;   4-Hydroxy-3-methoxybenzylacetone;   Formula=C11H14O3;   Gingerone;   InChI=1S/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H3;   InChIKey=OJYLAHXKWMRDGS-UHFFFAOYSA-N;   SMILES=COc1cc(CCC(C)=O)ccc1O;   Vanillylacetone;   Zingherone;   Zingiberone
 xref: CAS:122-48-5;   HMDB:HMDB0032590;   KEGG:C17497
 xref_mesh: MESH:C013738
 xref: PMID:18472135;   PMID:18670185;   PMID:19367122;   PMID:19459736;   PMID:19463966;   PMID:20211236;   PMID:20606379;   PMID:20713432;   PMID:20799069;   PMID:21335001;   PMID:21551955;   PMID:21769642;   PMID:21802408;   PMID:21929329;   PMID:22173270;   PMID:22329630;   PMID:22596078;   Patent:DE102009055915;   Patent:EP1336602;   Patent:EP2327393;   Patent:US2002051800;   Patent:US2003068276;   Patent:US5035882;   Patent:US5908770;   Patent:US6306429;   Patent:US6432441;   Patent:US6500797;   Patent:WO2011063863;   Patent:WO2011063864;   Patent:WO2011063865;   Reaxys:2051099;   Wikipedia:Zingerone


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zingerone term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Acaca acetyl-CoA carboxylase alpha multiple interactions EXP zingerone inhibits the reaction [[Cholesterol, Dietary co-treated with Cholic Acid] results in increased expression of ACACA mRNA] CTD PMID:33845646 NCBI chr10:69,014,261...69,276,453
Ensembl chr10:69,014,170...69,276,457 		JBrowse link
G Ache acetylcholinesterase multiple interactions
affects activity		 EXP zingerone affects the reaction [Vancomycin affects the activity of ACHE protein]
zingerone affects the activity of ACHE protein		 CTD PMID:31454121 NCBI chr12:19,406,133...19,413,713
Ensembl chr12:19,407,360...19,413,651 		JBrowse link
G Acox1 acyl-CoA oxidase 1 multiple interactions EXP zingerone inhibits the reaction [[Cholesterol, Dietary co-treated with Cholic Acid] results in decreased expression of ACOX1 mRNA] CTD PMID:33845646 NCBI chr10:101,406,197...101,431,252
Ensembl chr10:101,406,197...101,431,232 		JBrowse link
G Acsl1 acyl-CoA synthetase long-chain family member 1 multiple interactions EXP zingerone inhibits the reaction [[Cholesterol, Dietary co-treated with Cholic Acid] results in increased expression of ACSL1 mRNA] CTD PMID:33845646 NCBI chr16:45,755,246...45,821,541
Ensembl chr16:45,755,254...45,821,541 		JBrowse link
G Akt1 AKT serine/threonine kinase 1 multiple interactions ISO zingerone results in decreased expression of and results in decreased phosphorylation of AKT1 protein CTD PMID:32905641 NCBI chr 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921 		JBrowse link
G Akt2 AKT serine/threonine kinase 2 multiple interactions
increases expression		 EXP zingerone inhibits the reaction [[sodium arsenite results in increased abundance of Arsenic] which results in decreased expression of AKT2 mRNA]
zingerone results in increased expression of AKT2 mRNA		 CTD PMID:36822304 NCBI chr 1:82,877,228...82,933,828
Ensembl chr 1:82,883,547...82,933,817 		JBrowse link
G Ar androgen receptor multiple interactions ISO zingerone binds to and results in decreased activity of AR protein CTD PMID:20226658 NCBI chr  X:63,104,771...63,273,934
Ensembl chr  X:63,104,771...63,273,925 		JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions
increases expression		 EXP
ISO		 zingerone inhibits the reaction [[sodium arsenite results in increased abundance of Arsenic] which results in increased expression of BAX mRNA]; zingerone inhibits the reaction [[sodium arsenite results in increased abundance of Arsenic] which results in increased expression of BAX protein]; zingerone inhibits the reaction [Ethanol results in increased expression of BAX protein]
zingerone results in increased expression of BAX protein		 CTD PMID:28442378 PMID:31476248 PMID:36822304 NCBI chr 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368 		JBrowse link
G Bche butyrylcholinesterase affects activity
multiple interactions		 EXP zingerone affects the activity of BCHE protein
zingerone affects the reaction [Vancomycin affects the activity of BCHE protein]		 CTD PMID:31454121 NCBI chr 2:158,308,674...158,401,148
Ensembl chr 2:158,307,584...158,401,148 		JBrowse link
G Bcl2 BCL2, apoptosis regulator multiple interactions
decreases expression
increases expression		 EXP
ISO		 zingerone inhibits the reaction [[sodium arsenite results in increased abundance of Arsenic] which results in decreased expression of BCL2 mRNA]; zingerone inhibits the reaction [[sodium arsenite results in increased abundance of Arsenic] which results in decreased expression of BCL2 protein]; zingerone inhibits the reaction [Ethanol results in decreased expression of BCL2 protein]
zingerone results in decreased expression of BCL2 protein
zingerone results in increased expression of BCL2 mRNA		 CTD PMID:28442378 PMID:31476248 PMID:36822304 NCBI chr13:22,689,783...22,853,920
Ensembl chr13:22,684,989...22,853,743
Ensembl chr13:22,684,989...22,853,743 		JBrowse link
G Becn1 beclin 1 multiple interactions EXP zingerone inhibits the reaction [[sodium arsenite results in increased abundance of Arsenic] which results in increased expression of BECN1 mRNA] CTD PMID:36822304 NCBI chr10:86,231,387...86,246,742
Ensembl chr10:86,231,388...86,246,742 		JBrowse link
G Bid BH3 interacting domain death agonist increases expression ISO zingerone results in increased expression of BID protein CTD PMID:31476248 NCBI chr 4:154,113,198...154,136,353
Ensembl chr 4:154,113,198...154,134,720 		JBrowse link
G Casp3 caspase 3 multiple interactions EXP zingerone inhibits the reaction [[sodium arsenite results in increased abundance of Arsenic] which results in increased expression of CASP3 mRNA]; zingerone inhibits the reaction [Ethanol results in increased expression of CASP3 protein] CTD PMID:28442378 PMID:36822304 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Casp9 caspase 9 multiple interactions EXP zingerone inhibits the reaction [Ethanol results in increased expression of CASP9 protein] CTD PMID:28442378 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626 		JBrowse link
G Cat catalase multiple interactions EXP zingerone inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in decreased activity of CAT protein]; zingerone inhibits the reaction [[Cholesterol, Dietary co-treated with Cholic Acid] results in decreased activity of CAT protein]; zingerone inhibits the reaction [[sodium arsenite results in increased abundance of Arsenic] which results in decreased activity of CAT protein] CTD PMID:31476248 PMID:33845646 PMID:36822304 NCBI chr 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478 		JBrowse link
G Ccnd1 cyclin D1 multiple interactions EXP zingerone inhibits the reaction [1,2-Dimethylhydrazine results in increased expression of CCND1] CTD PMID:30720227 NCBI chr 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602 		JBrowse link
G Cpt1a carnitine palmitoyltransferase 1A multiple interactions EXP zingerone inhibits the reaction [[Cholesterol, Dietary co-treated with Cholic Acid] results in decreased expression of CPT1A mRNA] CTD PMID:33845646 NCBI chr 1:200,564,634...200,627,059
Ensembl chr 1:200,565,613...200,627,055 		JBrowse link
G Cyb5a cytochrome b5 type A multiple interactions EXP zingerone inhibits the reaction [Ethanol results in increased activity of CYB5A protein] CTD PMID:28442378 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 Cyb5r3 cytochrome b5 reductase 3 multiple interactions EXP zingerone inhibits the reaction [Ethanol results in increased activity of CYB5R3 protein] CTD PMID:28442378 NCBI chr 7:114,306,686...114,324,247
Ensembl chr 7:114,306,685...114,324,298 		JBrowse link
G Cyp2e1 cytochrome P450, family 2, subfamily e, polypeptide 1 multiple interactions EXP zingerone inhibits the reaction [1,2-Dimethylhydrazine results in increased expression of CYP2E1 protein]; zingerone inhibits the reaction [Ethanol results in increased activity of CYP2E1 protein] CTD PMID:28442378 PMID:30720227 NCBI chr 1:195,840,330...195,850,728
Ensembl chr 1:195,840,058...195,864,023 		JBrowse link
G Fasn fatty acid synthase multiple interactions EXP zingerone inhibits the reaction [[Cholesterol, Dietary co-treated with Cholic Acid] results in increased expression of FASN mRNA] CTD PMID:33845646 NCBI chr10:106,072,093...106,090,259
Ensembl chr10:106,072,091...106,090,261 		JBrowse link
G Foxo1 forkhead box O1 multiple interactions
increases expression		 EXP zingerone inhibits the reaction [[sodium arsenite results in increased abundance of Arsenic] which results in decreased expression of FOXO1 mRNA]
zingerone results in increased expression of FOXO1 mRNA		 CTD PMID:36822304 NCBI chr 2:136,312,168...136,390,603
Ensembl chr 2:136,312,168...136,387,790 		JBrowse link
G Gsr glutathione-disulfide reductase multiple interactions EXP zingerone inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in decreased activity of GSR protein] CTD PMID:31476248 NCBI chr16:58,482,209...58,525,256
Ensembl chr16:58,482,505...58,525,661 		JBrowse link
G Hmgcr 3-hydroxy-3-methylglutaryl-CoA reductase multiple interactions EXP zingerone inhibits the reaction [Ethanol results in increased activity of HMGCR protein] CTD PMID:28442378 NCBI chr 2:27,997,523...28,018,983
Ensembl chr 2:27,997,525...28,019,703 		JBrowse link
G Ifng interferon gamma multiple interactions ISO zingerone inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in increased expression of IFNG protein] CTD PMID:29289488 NCBI chr 7:53,903,339...53,907,375
Ensembl chr 7:53,903,337...53,907,375 		JBrowse link
G Il1b interleukin 1 beta multiple interactions
decreases expression		 EXP zingerone inhibits the reaction [[sodium arsenite results in increased abundance of Arsenic] which results in increased expression of IL1B mRNA]
zingerone results in decreased expression of IL1B mRNA; zingerone results in decreased expression of IL1B protein		 CTD PMID:36822304 NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415 		JBrowse link
G Il6 interleukin 6 multiple interactions ISO
EXP		 zingerone inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in increased expression of IL6 protein]
zingerone inhibits the reaction [1,2-Dimethylhydrazine results in increased expression of IL6 protein]; zingerone inhibits the reaction [[sodium arsenite results in increased abundance of Arsenic] which results in increased expression of IL6 mRNA]		 CTD PMID:29289488 PMID:30720227 PMID:36822304 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178 		JBrowse link
G Irf3 interferon regulatory factor 3 multiple interactions ISO zingerone inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in increased phosphorylation of IRF3 protein] CTD PMID:29289488 NCBI chr 1:95,479,966...95,484,926
Ensembl chr 1:95,479,821...95,484,935 		JBrowse link
G Lcat lecithin cholesterol acyltransferase multiple interactions EXP zingerone inhibits the reaction [Ethanol results in decreased activity of LCAT protein] CTD PMID:28442378 NCBI chr19:33,834,748...33,838,214
Ensembl chr19:33,834,403...33,838,231 		JBrowse link
G Lpl lipoprotein lipase multiple interactions EXP zingerone inhibits the reaction [Ethanol results in decreased activity of LPL protein] CTD PMID:28442378 NCBI chr16:20,830,055...20,853,855
Ensembl chr16:20,829,465...20,855,249 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 decreases phosphorylation EXP zingerone results in decreased phosphorylation of MAPK1 protein CTD PMID:20211236 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616 		JBrowse link
G Mapk14 mitogen activated protein kinase 14 multiple interactions EXP zingerone inhibits the reaction [[sodium arsenite results in increased abundance of Arsenic] which results in increased expression of MAPK14 mRNA] CTD PMID:36822304 NCBI chr20:6,749,646...6,810,590
Ensembl chr20:6,749,670...6,810,589 		JBrowse link
G Mapk15 mitogen-activated protein kinase 15 multiple interactions EXP zingerone inhibits the reaction [[sodium arsenite results in increased abundance of Arsenic] which results in increased expression of MAPK15 mRNA] CTD PMID:36822304 NCBI chr 7:107,694,907...107,714,640
Ensembl chr 7:107,694,964...107,714,645 		JBrowse link
G Mapk3 mitogen activated protein kinase 3 decreases phosphorylation EXP zingerone results in decreased phosphorylation of MAPK3 protein CTD PMID:20211236 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Mapk8 mitogen-activated protein kinase 8 multiple interactions
increases expression		 EXP zingerone inhibits the reaction [[sodium arsenite results in increased abundance of Arsenic] which results in increased expression of MAPK8 mRNA]
zingerone results in increased expression of MAPK8 mRNA		 CTD PMID:36822304 NCBI chr16:8,638,897...8,721,960
Ensembl chr16:8,638,924...8,721,981 		JBrowse link
G Mki67 marker of proliferation Ki-67 multiple interactions EXP zingerone inhibits the reaction [1,2-Dimethylhydrazine results in increased expression of MKI67 protein] CTD PMID:30720227 NCBI chr 1:190,496,319...190,522,983
Ensembl chr 1:190,496,319...190,522,762 		JBrowse link
G Mtor mechanistic target of rapamycin kinase multiple interactions ISO zingerone results in decreased expression of and results in decreased phosphorylation of MTOR protein CTD PMID:32905641 NCBI chr 5:158,884,856...158,994,311
Ensembl chr 5:158,884,804...158,994,311 		JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 2 multiple interactions EXP zingerone inhibits the reaction [1,2-Dimethylhydrazine results in increased expression of NFE2L2 protein] CTD PMID:30720227 NCBI chr 3:60,594,239...60,621,712
Ensembl chr 3:60,594,242...60,621,737 		JBrowse link
G Nfkb1 nuclear factor kappa B subunit 1 affects localization
decreases expression
multiple interactions		 EXP zingerone affects the localization of NFKB1 protein
zingerone results in decreased expression of NFKB1 mRNA
zingerone inhibits the reaction [[sodium arsenite results in increased abundance of Arsenic] which results in increased expression of NFKB1 mRNA]		 CTD PMID:20211236 PMID:36822304 NCBI chr 2:224,016,214...224,132,135
Ensembl chr 2:224,016,214...224,110,404 		JBrowse link
G Nfkbia NFKB inhibitor alpha multiple interactions ISO zingerone inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in decreased expression of NFKBIA protein] CTD PMID:29289488 NCBI chr 6:72,858,713...72,861,941
Ensembl chr 6:72,858,712...72,861,941 		JBrowse link
G Nos2 nitric oxide synthase 2 decreases expression
multiple interactions		 EXP zingerone results in decreased expression of NOS2 protein
zingerone inhibits the reaction [1,2-Dimethylhydrazine results in increased expression of NOS2 protein]; zingerone inhibits the reaction [[sodium arsenite results in increased abundance of Arsenic] which results in increased expression of NOS2 mRNA]		 CTD PMID:20211236 PMID:30720227 PMID:36822304 NCBI chr10:63,815,308...63,851,208
Ensembl chr10:63,815,308...63,851,210 		JBrowse link
G Nphs1 NPHS1 adhesion molecule, nephrin multiple interactions EXP zingerone inhibits the reaction [[sodium arsenite results in increased abundance of Arsenic] which results in decreased expression of NPHS1 protein] CTD PMID:36822304 NCBI chr 1:85,720,812...85,749,079
Ensembl chr 1:85,720,812...85,749,078 		JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 multiple interactions EXP zingerone inhibits the reaction [Ethanol results in decreased activity of NQO1 protein] CTD PMID:28442378 NCBI chr19:35,295,633...35,310,528
Ensembl chr19:35,295,573...35,310,557 		JBrowse link
G Nr1h3 nuclear receptor subfamily 1, group H, member 3 multiple interactions EXP zingerone inhibits the reaction [[Cholesterol, Dietary co-treated with Cholic Acid] results in increased expression of NR1H3 mRNA] CTD PMID:33845646 NCBI chr 3:77,158,808...77,168,907
Ensembl chr 3:77,158,808...77,168,722 		JBrowse link
G Or5d18 olfactory receptor family 5 subfamily D member 18 multiple interactions ISO zingerone binds to and results in increased activity of OR5D18 protein CTD PMID:21142015 NCBI chr 3:73,516,522...73,517,463
Ensembl chr 3:73,516,364...73,519,858
Ensembl chr 3:73,516,364...73,519,858 		JBrowse link
G Pcna proliferating cell nuclear antigen multiple interactions EXP zingerone inhibits the reaction [1,2-Dimethylhydrazine results in increased expression of PCNA protein] CTD PMID:30720227 NCBI chr 3:119,499,039...119,502,911
Ensembl chr 3:119,498,810...119,502,995 		JBrowse link
G Pon1 paraoxonase 1 multiple interactions
affects activity		 EXP zingerone affects the reaction [Vancomycin results in decreased activity of PON1 protein]
zingerone affects the activity of PON1 protein		 CTD PMID:31454121 NCBI chr 4:33,294,737...33,325,759
Ensembl chr 4:33,294,722...33,321,360 		JBrowse link
G Por cytochrome p450 oxidoreductase multiple interactions EXP zingerone inhibits the reaction [Ethanol results in increased activity of POR protein] CTD PMID:28442378 NCBI chr12:20,951,058...20,999,198
Ensembl chr12:20,951,058...20,999,245 		JBrowse link
G Ppara peroxisome proliferator activated receptor alpha multiple interactions EXP zingerone inhibits the reaction [[Cholesterol, Dietary co-treated with Cholic Acid] results in decreased expression of PPARA mRNA] CTD PMID:33845646 NCBI chr 7:116,832,405...116,900,878
Ensembl chr 7:116,832,756...116,895,346 		JBrowse link
G Psgb1 pregnancy-specific beta 1-glycoprotein multiple interactions EXP zingerone inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in increased expression of CEACAM5 protein] CTD PMID:31476248 NCBI chr 1:77,923,170...77,932,605
Ensembl chr 1:77,923,170...77,932,053 		JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 decreases expression
multiple interactions		 EXP zingerone results in decreased expression of PTGS2 protein
zingerone inhibits the reaction [1,2-Dimethylhydrazine results in increased expression of PTGS2 protein]; zingerone inhibits the reaction [[sodium arsenite results in increased abundance of Arsenic] which results in increased expression of PTGS2 mRNA]		 CTD PMID:20211236 PMID:30720227 PMID:36822304 NCBI chr13:62,163,936...62,172,193
Ensembl chr13:62,163,932...62,172,188 		JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions EXP zingerone affects the localization of and results in increased phosphorylation of RELA protein; zingerone inhibits the reaction [1,2-Dimethylhydrazine results in increased expression of RELA protein] CTD PMID:20211236 PMID:30720227 NCBI chr 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484 		JBrowse link
G Srebf1 sterol regulatory element binding transcription factor 1 multiple interactions EXP zingerone inhibits the reaction [[Cholesterol, Dietary co-treated with Cholic Acid] results in increased expression of SREBF1 mRNA] CTD PMID:33845646 NCBI chr10:45,007,637...45,029,650
Ensembl chr10:45,007,637...45,029,650 		JBrowse link
G Tgfb1 transforming growth factor, beta 1 multiple interactions EXP zingerone inhibits the reaction [Streptozocin results in increased expression of TGFB1 protein] CTD PMID:28904557 NCBI chr 1:81,196,532...81,212,848
Ensembl chr 1:81,196,532...81,212,847 		JBrowse link
G Tlr4 toll-like receptor 4 multiple interactions ISO zingerone inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in increased expression of TLR4 protein] CTD PMID:29289488 NCBI chr 5:80,145,867...80,159,501
Ensembl chr 5:80,145,826...80,159,628 		JBrowse link
G Tnf tumor necrosis factor multiple interactions
decreases expression		 ISO
EXP		 zingerone inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in increased expression of TNF protein]
zingerone inhibits the reaction [1,2-Dimethylhydrazine results in increased expression of TNF protein]; zingerone inhibits the reaction [[sodium arsenite results in increased abundance of Arsenic] which results in increased expression of TNF mRNA]
zingerone results in decreased expression of TNF mRNA		 CTD PMID:29289488 PMID:30720227 PMID:36822304 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629 		JBrowse link
G Tnni3 troponin I3, cardiac type multiple interactions EXP zingerone inhibits the reaction [[Cholesterol, Dietary co-treated with Cholic Acid] results in increased expression of TNNI3 protein] CTD PMID:33845646 NCBI chr 1:69,299,900...69,303,582
Ensembl chr 1:69,299,900...69,303,580 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19867
    role 19837
      chemical role 19467
        antioxidant 16172
          zingerone 55
Path 2
Term Annotations click to browse term
  CHEBI ontology 19867
    subatomic particle 19865
      composite particle 19865
        hadron 19865
          baryon 19865
            nucleon 19865
              atomic nucleus 19865
                atom 19865
                  main group element atom 19803
                    p-block element atom 19803
                      carbon group element atom 19744
                        carbon atom 19740
                          organic molecular entity 19740
                            organic molecule 19692
                              organic cyclic compound 19482
                                carbocyclic compound 18587
                                  benzenoid aromatic compound 18009
                                    benzenes 17877
                                      methoxybenzenes 2063
                                        monomethoxybenzene 1864
                                          zingerone 55
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