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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:zerumbone
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Accession:CHEBI:63892 term browser browse the term
Definition:A sesquiterpenoid and cyclic ketone that is (1E,4E,8E)-alpha-humulene which is substituted by an oxo group at the carbon atom attached to two double bonds. It is obtained by steam distillation from a type of edible ginger, Zingiber zerumbet Smith, grown particularly in southeast Asia.
Synonyms:exact_synonym: (2E,6E,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one
 related_synonym: (E,E,E)-2,6,9,9-tetramethyl-2,6,10-cycloundecatrien-1-one;   2E,6E,9E-humulatrien-8-one;   Formula=C15H22O;   InChI=1S/C15H22O/c1-12-6-5-7-13(2)14(16)9-11-15(3,4)10-8-12/h7-9,11H,5-6,10H2,1-4H3/b11-9+,12-8+,13-7+;   InChIKey=GIHNTRQPEMKFKO-SKTNYSRSSA-N;   SMILES=C\\C1=C/CC(C)(C)\\C=C\\C(=O)\\C(C)=C\\CC1
 xref: CAS:471-05-6;   KEGG:C20262
 xref_mesh: MESH:C403304
 xref: MetaCyc:CPD-11421;   PMID:15997145;   PMID:1804548;   PMID:19343171;   PMID:20546845;   PMID:20708800;   PMID:20955360;   PMID:21307568;   PMID:21367956;   PMID:21423870;   PMID:21527993;   PMID:21668645;   Patent:US2009239953;   Reaxys:3199411


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zerumbone term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Akt1 AKT serine/threonine kinase 1 multiple interactions ISO zerumbone inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in increased phosphorylation of AKT1 protein] CTD PMID:28442377 NCBI chr 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921 		JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions
increases expression		 EXP
ISO		 zerumbone promotes the reaction [[2-aminofluorene co-treated with Diethylnitrosamine] results in increased expression of BAX protein]
zerumbone analog results in increased expression of BAX protein		 CTD PMID:20452335 PMID:28987329 NCBI chr 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368 		JBrowse link
G Bbc3 Bcl-2 binding component 3 increases expression ISO zerumbone results in increased expression of BBC3 mRNA CTD PMID:36122806 NCBI chr 1:77,013,281...77,022,509
Ensembl chr 1:77,014,543...77,022,509 		JBrowse link
G Bcl2 BCL2, apoptosis regulator decreases expression
multiple interactions		 ISO
EXP		 zerumbone analog results in decreased expression of BCL2 protein; zerumbone results in decreased expression of BCL2 mRNA
zerumbone inhibits the reaction [[2-aminofluorene co-treated with Diethylnitrosamine] results in increased expression of BCL2 protein]		 CTD PMID:16007145 PMID:20452335 PMID:28987329 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 Bcl2a1 BCL2-related protein A1 decreases expression ISO zerumbone results in decreased expression of BCL2A1 mRNA CTD PMID:16007145 NCBI chr 8:89,716,914...89,724,998
Ensembl chr 8:89,716,914...89,724,998 		JBrowse link
G Bcl2l1 Bcl2-like 1 decreases expression ISO zerumbone results in decreased expression of BCL2L1 mRNA CTD PMID:16007145 NCBI chr 3:141,253,508...141,304,582
Ensembl chr 3:141,253,523...141,303,479 		JBrowse link
G Birc2 baculoviral IAP repeat-containing 2 decreases expression ISO zerumbone results in decreased expression of BIRC2 mRNA CTD PMID:16007145 NCBI chr 8:4,968,856...4,989,325
Ensembl chr 8:4,968,842...4,988,732 		JBrowse link
G Birc3 baculoviral IAP repeat-containing 3 decreases expression ISO zerumbone results in decreased expression of BIRC3 mRNA CTD PMID:16007145 NCBI chr 8:5,000,844...5,028,470
Ensembl chr 8:5,000,845...5,015,802 		JBrowse link
G Birc5 baculoviral IAP repeat-containing 5 decreases expression ISO zerumbone results in decreased expression of BIRC5 mRNA CTD PMID:16007145 PMID:36122806 NCBI chr10:103,072,530...103,081,382
Ensembl chr10:103,073,408...103,081,380 		JBrowse link
G Casp3 caspase 3 multiple interactions ISO zerumbone analog results in increased activity of and results in increased cleavage of CASP3 protein CTD PMID:28987329 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Ccnd1 cyclin D1 decreases expression ISO zerumbone results in decreased expression of CCND1 mRNA CTD PMID:16007145 NCBI chr 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602 		JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A increases expression ISO zerumbone results in increased expression of CDKN1A mRNA CTD PMID:36122806 NCBI chr20:7,149,177...7,159,727
Ensembl chr20:7,149,217...7,159,585 		JBrowse link
G Cflar CASP8 and FADD-like apoptosis regulator decreases expression ISO zerumbone results in decreased expression of CFLAR mRNA CTD PMID:16007145 NCBI chr 9:60,185,338...60,236,173
Ensembl chr 9:60,185,452...60,237,034 		JBrowse link
G Chuk component of inhibitor of nuclear factor kappa B kinase complex multiple interactions ISO zerumbone inhibits the reaction [CHUK protein results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone inhibits the reaction [TNF protein results in increased activity of CHUK protein] CTD PMID:16007145 NCBI chr 1:242,959,539...242,995,066
Ensembl chr 1:242,959,760...242,995,065 		JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 decreases expression ISO zerumbone results in decreased expression of CYP1A1 mRNA CTD PMID:36122806 NCBI chr 8:58,096,021...58,102,130
Ensembl chr 8:58,096,077...58,102,125 		JBrowse link
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 increases expression ISO zerumbone results in increased expression of CYP1A2 mRNA CTD PMID:36122806 NCBI chr 8:58,075,367...58,082,255
Ensembl chr 8:58,075,367...58,082,312 		JBrowse link
G Cyp2c6 cytochrome P450, family 2, subfamily C, polypeptide 6 increases expression ISO zerumbone results in increased expression of CYP2C19 mRNA CTD PMID:36122806 NCBI chr 1:237,938,521...237,976,238
Ensembl chr 1:237,693,094...238,057,596 		JBrowse link
G Cyp2d4 cytochrome P450, family 2, subfamily d, polypeptide 4 decreases expression ISO zerumbone results in decreased expression of CYP2D6 mRNA CTD PMID:36122806 NCBI chr 7:113,882,584...113,891,754
Ensembl chr 7:113,881,618...113,891,759 		JBrowse link
G Ern1 endoplasmic reticulum to nucleus signaling 1 increases expression ISO zerumbone results in increased expression of ERN1 mRNA CTD PMID:36122806 NCBI chr10:91,326,889...91,421,201
Ensembl chr10:91,330,654...91,421,029 		JBrowse link
G Gadd45a growth arrest and DNA-damage-inducible, alpha increases expression ISO zerumbone results in increased expression of GADD45A mRNA CTD PMID:36122806 NCBI chr 4:96,154,789...96,157,091
Ensembl chr 4:96,154,789...96,157,115 		JBrowse link
G Gpx1 glutathione peroxidase 1 increases expression ISO zerumbone results in increased expression of GPX1 mRNA CTD PMID:15122579 NCBI chr 8:109,026,905...109,028,031
Ensembl chr 8:109,026,905...109,028,024 		JBrowse link
G Gstp1 glutathione S-transferase pi 1 increases expression ISO zerumbone results in increased expression of GSTP1 mRNA CTD PMID:15122579 NCBI chr 1:201,337,762...201,340,230
Ensembl chr 1:201,321,672...201,340,226 		JBrowse link
G Icam1 intercellular adhesion molecule 1 decreases expression ISO zerumbone results in decreased expression of ICAM1 mRNA CTD PMID:16007145 NCBI chr 8:19,553,063...19,565,438
Ensembl chr 8:19,553,645...19,565,438 		JBrowse link
G Igf1 insulin-like growth factor 1 decreases expression ISO zerumbone results in decreased expression of IGF1 mRNA CTD PMID:36122806 NCBI chr 7:22,282,895...22,361,972
Ensembl chr 7:22,282,930...22,359,296 		JBrowse link
G Ikbkb inhibitor of nuclear factor kappa B kinase subunit beta multiple interactions ISO zerumbone inhibits the reaction [TNF protein results in increased activity of IKBKB protein] CTD PMID:16007145 NCBI chr16:69,319,487...69,373,251
Ensembl chr16:69,319,554...69,373,250 		JBrowse link
G Il1b interleukin 1 beta decreases expression
multiple interactions
decreases secretion		 ISO zerumbone results in decreased expression of IL1B mRNA
zerumbone inhibits the reaction [IL1B protein results in increased expression of IL1B mRNA]; zerumbone inhibits the reaction [IL1B protein results in increased phosphorylation of RELA protein]
zerumbone results in decreased secretion of IL1B protein		 CTD PMID:27567548 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 zerumbone inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in increased expression of IL6 protein] CTD PMID:28442377 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178 		JBrowse link
G Map1lc3a microtubule-associated protein 1 light chain 3 alpha decreases expression ISO zerumbone results in decreased expression of MAP1LC3A mRNA CTD PMID:36122806 NCBI chr 3:143,783,024...143,784,670
Ensembl chr 3:143,783,024...143,784,670 		JBrowse link
G Map3k14 mitogen-activated protein kinase kinase kinase 14 multiple interactions ISO zerumbone inhibits the reaction [MAP3K14 protein results in increased activity of [NFKB1 protein binds to RELA protein]] CTD PMID:16007145 NCBI chr10:88,165,349...88,215,558
Ensembl chr10:88,165,351...88,215,523 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions ISO zerumbone inhibits the reaction [Tetradecanoylphorbol Acetate results in increased phosphorylation of MAPK1 protein] CTD PMID:15122579 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616 		JBrowse link
G Mapk3 mitogen activated protein kinase 3 multiple interactions ISO zerumbone inhibits the reaction [Tetradecanoylphorbol Acetate results in increased phosphorylation of MAPK3 protein] CTD PMID:15122579 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Mmp2 matrix metallopeptidase 2 multiple interactions ISO zerumbone analog results in decreased expression of and results in decreased secretion of MMP2 protein CTD PMID:28987329 NCBI chr19:14,154,657...14,182,870
Ensembl chr19:14,154,657...14,182,870 		JBrowse link
G Mmp3 matrix metallopeptidase 3 multiple interactions ISO zerumbone inhibits the reaction [DDT results in increased expression of MMP3 mRNA]; zerumbone inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of MMP3 mRNA] CTD PMID:20865247 NCBI chr 8:4,640,397...4,653,963
Ensembl chr 8:4,640,416...4,653,961 		JBrowse link
G Mmp9 matrix metallopeptidase 9 decreases expression
multiple interactions		 ISO zerumbone results in decreased expression of MMP9 mRNA
zerumbone analog results in decreased expression of and results in decreased secretion of MMP9 protein		 CTD PMID:16007145 PMID:28987329 NCBI chr 3:153,684,158...153,692,118
Ensembl chr 3:153,683,858...153,692,120 		JBrowse link
G Myc MYC proto-oncogene, bHLH transcription factor decreases expression ISO zerumbone results in decreased expression of MYC mRNA CTD PMID:16007145 PMID:36122806 NCBI chr 7:93,593,705...93,598,633
Ensembl chr 7:93,593,705...93,598,630 		JBrowse link
G Nfkb1 nuclear factor kappa B subunit 1 multiple interactions
decreases expression		 ISO zerumbone inhibits the reaction [CHUK protein results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone inhibits the reaction [Hydrogen Peroxide results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone inhibits the reaction [MAP3K14 protein results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone inhibits the reaction [Okadaic Acid results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone inhibits the reaction [Tetradecanoylphorbol Acetate results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone inhibits the reaction [TNF protein results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone inhibits the reaction [TNFRSF1A protein results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone inhibits the reaction [TRADD protein results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone inhibits the reaction [TRAF2 protein results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone results in decreased activity of [NFKB1 protein binds to RELA protein]
zerumbone results in decreased expression of NFKB1 mRNA		 CTD PMID:16007145 PMID:36122806 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 zerumbone inhibits the reaction [TNF protein results in increased degradation of NFKBIA protein]; zerumbone inhibits the reaction [TNF protein results in increased phosphorylation of NFKBIA protein] CTD PMID:16007145 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 multiple interactions ISO zerumbone inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in increased expression of NOS2 protein] CTD PMID:28442377 NCBI chr10:63,815,308...63,851,208
Ensembl chr10:63,815,308...63,851,210 		JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 increases expression ISO zerumbone results in increased expression of NQO1 mRNA CTD PMID:15122579 NCBI chr19:35,295,633...35,310,528
Ensembl chr19:35,295,573...35,310,557 		JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 increases cleavage
decreases expression		 ISO zerumbone analog results in increased cleavage of PARP1 protein; zerumbone results in increased cleavage of PARP1 protein
zerumbone results in decreased expression of PARP1 mRNA		 CTD PMID:16007145 PMID:28987329 PMID:36122806 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404 		JBrowse link
G Pcna proliferating cell nuclear antigen multiple interactions EXP zerumbone inhibits the reaction [[2-aminofluorene co-treated with Diethylnitrosamine] results in increased expression of PCNA protein] CTD PMID:20452335 NCBI chr 3:119,499,039...119,502,911
Ensembl chr 3:119,498,810...119,502,995 		JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions
decreases expression		 ISO zerumbone inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in increased expression of PTGS2 protein]; zerumbone inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of PTGS2 mRNA]; zerumbone inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of PTGS2 protein]
zerumbone results in decreased expression of PTGS2 mRNA
zerumbone inhibits the reaction [DDT results in increased expression of PTGS2 mRNA]; zerumbone inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of PTGS2 mRNA]		 CTD PMID:15122579 PMID:16007145 PMID:20865247 PMID:28442377 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
decreases phosphorylation		 ISO zerumbone inhibits the reaction [CHUK protein results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone inhibits the reaction [Hydrogen Peroxide results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone inhibits the reaction [IL1B protein results in increased phosphorylation of RELA protein]; zerumbone inhibits the reaction [MAP3K14 protein results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone inhibits the reaction [Okadaic Acid results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone inhibits the reaction [Tetradecanoylphorbol Acetate results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone inhibits the reaction [TNF protein results in increased acetylation of RELA protein]; zerumbone inhibits the reaction [TNF protein results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone inhibits the reaction [TNF protein results in increased phosphorylation of and affects the localization of RELA protein]; zerumbone inhibits the reaction [TNFRSF1A protein results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone inhibits the reaction [TRADD protein results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone inhibits the reaction [TRAF2 protein results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone results in decreased activity of [NFKB1 protein binds to RELA protein]
zerumbone results in decreased phosphorylation of RELA protein		 CTD PMID:16007145 PMID:27567548 NCBI chr 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484 		JBrowse link
G Sod2 superoxide dismutase 2 increases expression ISO zerumbone results in increased expression of SOD2 mRNA CTD PMID:15122579 NCBI chr 1:47,638,318...47,645,163
Ensembl chr 1:47,636,528...47,645,189 		JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO zerumbone inhibits the reaction [TNF protein results in increased acetylation of RELA protein]; zerumbone inhibits the reaction [TNF protein results in increased activity of [NFKB1 protein binds to RELA protein]]; zerumbone inhibits the reaction [TNF protein results in increased activity of CHUK protein]; zerumbone inhibits the reaction [TNF protein results in increased activity of IKBKB protein]; zerumbone inhibits the reaction [TNF protein results in increased degradation of NFKBIA protein]; zerumbone inhibits the reaction [TNF protein results in increased phosphorylation of and affects the localization of RELA protein]; zerumbone inhibits the reaction [TNF protein results in increased phosphorylation of NFKBIA protein]
zerumbone inhibits the reaction [lipopolysaccharide, Escherichia coli O111 B4 results in increased expression of TNF protein]		 CTD PMID:16007145 PMID:28442377 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629 		JBrowse link
G Tnfrsf1a TNF receptor superfamily member 1A multiple interactions ISO zerumbone inhibits the reaction [TNFRSF1A protein results in increased activity of [NFKB1 protein binds to RELA protein]] CTD PMID:16007145 NCBI chr 4:158,150,815...158,163,592
Ensembl chr 4:158,150,820...158,163,591 		JBrowse link
G Tp53 tumor protein p53 decreases expression ISO zerumbone results in decreased expression of TP53 mRNA CTD PMID:36122806 NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524 		JBrowse link
G Tradd TNFRSF1A-associated via death domain multiple interactions ISO zerumbone inhibits the reaction [TRADD protein results in increased activity of [NFKB1 protein binds to RELA protein]] CTD PMID:16007145 NCBI chr19:33,136,148...33,142,714
Ensembl chr19:33,136,138...33,142,638 		JBrowse link
G Traf1 TNF receptor-associated factor 1 decreases expression ISO zerumbone results in decreased expression of TRAF1 mRNA CTD PMID:16007145 NCBI chr 3:18,222,024...18,242,163
Ensembl chr 3:18,222,054...18,241,807 		JBrowse link
G Traf2 Tnf receptor-associated factor 2 multiple interactions ISO zerumbone inhibits the reaction [TRAF2 protein results in increased activity of [NFKB1 protein binds to RELA protein]] CTD PMID:16007145 NCBI chr 3:8,341,950...8,366,609
Ensembl chr 3:8,341,951...8,366,538 		JBrowse link
G Vegfa vascular endothelial growth factor A multiple interactions
decreases expression		 ISO zerumbone inhibits the reaction [DDT results in increased expression of VEGFA mRNA]; zerumbone inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of VEGFA mRNA]
zerumbone analog results in decreased expression of VEGFA protein		 CTD PMID:20865247 PMID:28987329 NCBI chr 9:14,955,300...14,970,641
Ensembl chr 9:14,955,300...14,970,641 		JBrowse link
G Xiap X-linked inhibitor of apoptosis decreases expression ISO zerumbone results in decreased expression of XIAP mRNA CTD PMID:16007145 NCBI chr  X:120,890,537...120,938,413
Ensembl chr  X:120,897,907...120,934,700 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19898
    role 19868
      application 19714
        anti-inflammatory agent 16684
          zerumbone 52
            5-hydroxyzerumbone 0
            zerumboneoxide 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19898
    subatomic particle 19896
      composite particle 19896
        hadron 19896
          baryon 19896
            nucleon 19896
              atomic nucleus 19896
                atom 19896
                  main group element atom 19835
                    main group molecular entity 19835
                      s-block molecular entity 19670
                        hydrogen molecular entity 19651
                          hydrides 19158
                            organic hydride 18704
                              organic fundamental parent 18704
                                hydrocarbon 18452
                                  terpene 14074
                                    sesquiterpene 3289
                                      humulane 52
                                        humulene 52
                                          alpha-humulene 52
                                            zerumbone 52
                                              5-hydroxyzerumbone 0
                                              zerumboneoxide 0
paths to the root