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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:nobiletin
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Accession:CHEBI:7602 term browser browse the term
Definition:A methoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 8, 3' and 4' respectively.
Synonyms:exact_synonym: 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one
 related_synonym: 5,6,7,8,3',4'-Hexamethoxyflavone;   Formula=C21H22O8;   Hexamethoxyflavone;   InChI=1S/C21H22O8/c1-23-13-8-7-11(9-15(13)24-2)14-10-12(22)16-17(25-3)19(26-4)21(28-6)20(27-5)18(16)29-14/h7-10H,1-6H3;   InChIKey=MRIAQLRQZPPODS-UHFFFAOYSA-N;   SMILES=COc1ccc(cc1OC)-c1cc(=O)c2c(OC)c(OC)c(OC)c(OC)c2o1
 xref: CAS:478-01-3;   HMDB:HMDB0029540;   KEGG:C10112;   KNApSAcK:C00001076;   LINCS:LSM-2130;   LIPID_MAPS_instance:LMPK12111468
 xref_mesh: MESH:C008661
 xref: PMID:25488359;   PMID:25845666;   Reaxys:360887;   Wikipedia:Nobiletin



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nobiletin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb1a ATP binding cassette subfamily B member 1A multiple interactions ISO nobiletin inhibits the reaction [ABCB1 protein results in increased transport of Digoxin]; nobiletin promotes the reaction [ABCB1 protein results in increased hydrolysis of Adenosine Triphosphate]; nobiletin promotes the reaction [ABCB1 protein results in increased import of Daunorubicin] CTD PMID:18955043 PMID:30790579 NCBI chr 4:25,357,467...25,529,941
Ensembl chr 4:25,158,362...25,442,709
JBrowse link
G Abcc1 ATP binding cassette subfamily C member 1 multiple interactions ISO nobiletin promotes the reaction [ABCC1 protein results in increased hydrolysis of Adenosine Triphosphate]; nobiletin promotes the reaction [ABCC1 protein results in increased import of fluorexon] CTD PMID:18955043 NCBI chr10:528,961...655,179
Ensembl chr10:531,812...655,114
JBrowse link
G Akt1 AKT serine/threonine kinase 1 multiple interactions ISO
EXP
[nobiletin co-treated with Hydrogen Peroxide] results in increased phosphorylation of AKT1 protein
[paeonol co-treated with icariin co-treated with nobiletin co-treated with Ginsenosides co-treated with astragaloside A] results in decreased expression of AKT1 mRNA; [paeonol co-treated with icariin co-treated with nobiletin co-treated with Ginsenosides co-treated with astragaloside A] results in decreased expression of and results in decreased phosphorylation of AKT1 protein
CTD PMID:29687528 PMID:32344236 NCBI chr 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921
JBrowse link
G Asns asparagine synthetase (glutamine-hydrolyzing) increases expression ISO
EXP
nobiletin results in increased expression of ASNS mRNA; nobiletin results in increased expression of ASNS protein CTD PMID:23321314 NCBI chr 4:35,784,995...35,803,474
Ensembl chr 4:35,785,237...35,803,423
JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions ISO nobiletin inhibits the reaction [Hydrogen Peroxide results in increased expression of BAX protein] CTD PMID:29687528 NCBI chr 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368
JBrowse link
G Bcl2 BCL2, apoptosis regulator multiple interactions ISO nobiletin inhibits the reaction [Hydrogen Peroxide results in decreased expression of BCL2 protein] CTD PMID:29687528 NCBI chr13:22,689,783...22,853,920 JBrowse link
G Casp3 caspase 3 multiple interactions ISO AGN 193109 inhibits the reaction [nobiletin results in decreased expression of and results in increased cleavage of CASP3 protein]; nobiletin results in decreased expression of and results in increased cleavage of CASP3 protein CTD PMID:33058988 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648
JBrowse link
G Casp8 caspase 8 multiple interactions
increases cleavage
ISO AGN 193109 inhibits the reaction [nobiletin results in increased cleavage of CASP8 protein] CTD PMID:33058988 NCBI chr 9:60,263,863...60,312,542
Ensembl chr 9:60,264,075...60,312,542
JBrowse link
G Casp9 caspase 9 multiple interactions ISO AGN 193109 inhibits the reaction [nobiletin results in decreased expression of and results in increased cleavage of CASP9 protein]; nobiletin results in decreased expression of and results in increased cleavage of CASP9 protein CTD PMID:33058988 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626
JBrowse link
G Ccna2 cyclin A2 decreases expression ISO
EXP
nobiletin results in decreased expression of CCNA2 mRNA CTD PMID:23321314 NCBI chr 2:119,427,239...119,433,645
Ensembl chr 2:119,426,089...119,433,577
JBrowse link
G Ccne2 cyclin E2 decreases expression ISO
EXP
nobiletin results in decreased expression of CCNE2 mRNA CTD PMID:23321314 NCBI chr 5:24,285,078...24,298,258
Ensembl chr 5:24,284,922...24,297,632
JBrowse link
G Cd74 CD74 molecule decreases expression ISO nobiletin results in decreased expression of CD74 mRNA CTD PMID:18818744 NCBI chr18:54,256,757...54,266,003
Ensembl chr18:54,256,778...54,266,003
JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 increases metabolic processing
increases expression
multiple interactions
ISO CYP1A1 protein results in increased metabolism of nobiletin
nobiletin results in increased expression of CYP1A1 protein
nobiletin inhibits the reaction [DDT results in increased expression of CYP1A1 mRNA]; nobiletin inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of CYP1A1 mRNA]
CTD PMID:20865247 PMID:22743247 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 metabolic processing ISO CYP1A2 protein results in increased metabolism of nobiletin CTD PMID:22743247 NCBI chr 8:58,075,367...58,082,255
Ensembl chr 8:58,075,367...58,082,312
JBrowse link
G Cyp1b1 cytochrome P450, family 1, subfamily b, polypeptide 1 increases expression ISO nobiletin results in increased expression of CYP1B1 mRNA CTD PMID:22743247 NCBI chr 6:15,342,312...15,350,886
Ensembl chr 6:15,342,344...15,350,917
JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 increases activity
multiple interactions
ISO nobiletin results in increased activity of CYP3A4 protein
[[nobiletin results in increased activity of CYP3A4 protein] which results in increased metabolism of Midazolam] which results in increased chemical synthesis of 1-hydroxymethylmidazolam; [nobiletin results in increased activity of CYP3A4 protein] which results in increased metabolism of Midazolam
CTD PMID:31756459 NCBI chr12:9,207,986...9,230,038
Ensembl chr12:9,015,383...9,285,008
JBrowse link
G Ddit3 DNA-damage inducible transcript 3 increases expression ISO
EXP
nobiletin results in increased expression of DDIT3 mRNA; nobiletin results in increased expression of DDIT3 protein CTD PMID:23321314 NCBI chr 7:63,115,645...63,121,203
Ensembl chr 7:63,116,380...63,121,201
JBrowse link
G Depdc1 DEP domain containing 1 decreases expression ISO
EXP
nobiletin results in decreased expression of DEPDC1 mRNA CTD PMID:23321314 NCBI chr 2:248,684,508...248,717,951
Ensembl chr 2:248,684,523...248,717,951
JBrowse link
G E2f8 E2F transcription factor 8 decreases expression ISO
EXP
nobiletin results in decreased expression of E2F8 mRNA CTD PMID:23321314 NCBI chr 1:98,565,717...98,584,265
Ensembl chr 1:98,565,717...98,584,098
JBrowse link
G Egfr epidermal growth factor receptor multiple interactions EXP [paeonol co-treated with icariin co-treated with nobiletin co-treated with Ginsenosides co-treated with astragaloside A] results in decreased expression of and results in decreased phosphorylation of EGFR protein; [paeonol co-treated with icariin co-treated with nobiletin co-treated with Ginsenosides co-treated with astragaloside A] results in decreased expression of EGFR mRNA CTD PMID:32344236 NCBI chr14:91,176,931...91,349,722
Ensembl chr14:91,177,067...91,344,382
JBrowse link
G Fos Fos proto-oncogene, AP-1 transcription factor subunit increases expression EXP nobiletin results in increased expression of FOS mRNA CTD PMID:24964900 NCBI chr 6:105,121,170...105,124,036
Ensembl chr 6:105,121,170...105,124,036
JBrowse link
G Gpt glutamic--pyruvic transaminase multiple interactions EXP nobiletin inhibits the reaction [Acetaminophen results in increased expression of GPT protein] CTD PMID:31777137 NCBI chr 7:108,416,646...108,419,495
Ensembl chr 7:108,416,642...108,419,494
JBrowse link
G Grin1 glutamate ionotropic receptor NMDA type subunit 1 increases expression EXP nobiletin results in increased expression of GRIN1 mRNA CTD PMID:24964900 NCBI chr 3:8,103,680...8,130,603
Ensembl chr 3:8,103,680...8,130,603
JBrowse link
G Grin2a glutamate ionotropic receptor NMDA type subunit 2A increases expression EXP nobiletin results in increased expression of GRIN2A mRNA CTD PMID:24964900 NCBI chr10:5,630,684...6,043,341
Ensembl chr10:5,631,369...6,044,637
JBrowse link
G Grin2b glutamate ionotropic receptor NMDA type subunit 2B increases expression EXP nobiletin results in increased expression of GRIN2B mRNA CTD PMID:24964900 NCBI chr 4:168,580,824...169,044,110
Ensembl chr 4:168,599,546...169,042,279
JBrowse link
G H1f5 H1.5 linker histone, cluster member decreases expression ISO
EXP
nobiletin results in decreased expression of H1-5 mRNA
nobiletin results in decreased expression of H1F5 mRNA
CTD PMID:23321314 NCBI chr17:42,726,189...42,726,857
Ensembl chr17:42,726,127...42,769,160
JBrowse link
G Hmox1 heme oxygenase 1 multiple interactions EXP nobiletin inhibits the reaction [Acetaminophen results in decreased expression of HMOX1 protein] CTD PMID:31777137 NCBI chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079
JBrowse link
G Il1b interleukin 1 beta multiple interactions EXP [paeonol co-treated with icariin co-treated with nobiletin co-treated with Ginsenosides co-treated with astragaloside A] results in decreased secretion of IL1B protein; nobiletin inhibits the reaction [Acetaminophen results in increased expression of IL1B protein] CTD PMID:31777137 PMID:32344236 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 EXP [paeonol co-treated with icariin co-treated with nobiletin co-treated with Ginsenosides co-treated with astragaloside A] results in decreased secretion of IL6 protein; nobiletin inhibits the reaction [Acetaminophen results in increased expression of IL6 protein] CTD PMID:31777137 PMID:32344236 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178
JBrowse link
G Kif11 kinesin family member 11 decreases expression ISO
EXP
nobiletin results in decreased expression of KIF11 mRNA CTD PMID:23321314 NCBI chr 1:235,124,371...235,176,760
Ensembl chr 1:235,124,316...235,176,766
JBrowse link
G Mmp7 matrix metallopeptidase 7 decreases expression ISO nobiletin results in decreased expression of MMP7 mRNA; nobiletin results in decreased expression of MMP7 protein CTD PMID:15725655 NCBI chr 8:4,848,186...4,855,908
Ensembl chr 8:4,848,186...4,855,902
JBrowse link
G Mmp9 matrix metallopeptidase 9 multiple interactions EXP [paeonol co-treated with icariin co-treated with nobiletin co-treated with Ginsenosides co-treated with astragaloside A] affects the secretion of MMP9 protein CTD PMID:32344236 NCBI chr 3:153,684,158...153,692,118
Ensembl chr 3:153,683,858...153,692,120
JBrowse link
G Mtor mechanistic target of rapamycin kinase multiple interactions EXP [paeonol co-treated with icariin co-treated with nobiletin co-treated with Ginsenosides co-treated with astragaloside A] results in decreased expression of and results in decreased phosphorylation of MTOR protein; [paeonol co-treated with icariin co-treated with nobiletin co-treated with Ginsenosides co-treated with astragaloside A] results in decreased expression of MTOR mRNA CTD PMID:32344236 NCBI chr 5:158,884,856...158,994,311
Ensembl chr 5:158,884,804...158,994,311
JBrowse link
G Muc5ac mucin 5AC, oligomeric mucus/gel-forming multiple interactions EXP [paeonol co-treated with icariin co-treated with nobiletin co-treated with Ginsenosides co-treated with astragaloside A] results in decreased expression of MUC5AC mRNA; [paeonol co-treated with icariin co-treated with nobiletin co-treated with Ginsenosides co-treated with astragaloside A] results in decreased secretion of MUC5AC protein CTD PMID:32344236 NCBI chr 1:196,864,375...196,896,475 JBrowse link
G Muc5b mucin 5B, oligomeric mucus/gel-forming multiple interactions EXP [paeonol co-treated with icariin co-treated with nobiletin co-treated with Ginsenosides co-treated with astragaloside A] results in decreased expression of MUC5B mRNA CTD PMID:32344236 NCBI chr 1:196,916,861...196,948,830
Ensembl chr 1:196,916,825...196,949,250
JBrowse link
G Nfe2l2 nuclear factor, erythroid 2-like 2 multiple interactions EXP nobiletin inhibits the reaction [Acetaminophen results in decreased expression of NFE2L2 protein] CTD PMID:31777137 NCBI chr 3:60,594,239...60,621,785
Ensembl chr 3:60,594,242...60,621,737
JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 multiple interactions ISO AGN 193109 inhibits the reaction [nobiletin results in decreased expression of and results in increased cleavage of PARP1 protein]; nobiletin results in decreased expression of and results in increased cleavage of PARP1 protein CTD PMID:33058988 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404
JBrowse link
G Rarb retinoic acid receptor, beta multiple interactions
increases expression
ISO AGN 193109 inhibits the reaction [nobiletin results in increased expression of RARB protein]
nobiletin results in increased expression of RARB mRNA; nobiletin results in increased expression of RARB protein
CTD PMID:33058988 NCBI chr15:8,700,533...9,051,288
Ensembl chr15:8,406,492...9,051,288
JBrowse link
G Slc6a9 solute carrier family 6 member 9 increases expression ISO
EXP
nobiletin results in increased expression of SLC6A9 mRNA CTD PMID:23321314 NCBI chr 5:131,374,562...131,408,733
Ensembl chr 5:131,374,542...131,408,728
JBrowse link
G Timp1 TIMP metallopeptidase inhibitor 1 multiple interactions EXP [paeonol co-treated with icariin co-treated with nobiletin co-treated with Ginsenosides co-treated with astragaloside A] affects the secretion of TIMP1 protein CTD PMID:32344236 NCBI chr  X:1,212,969...1,217,714
Ensembl chr  X:1,212,972...1,217,664
JBrowse link
G Tmem116 transmembrane protein 116 increases expression ISO
EXP
nobiletin results in increased expression of TMEM116 mRNA CTD PMID:23321314 NCBI chr12:35,021,912...35,089,409
Ensembl chr12:35,041,572...35,089,430
JBrowse link
G Tnf tumor necrosis factor multiple interactions EXP [paeonol co-treated with icariin co-treated with nobiletin co-treated with Ginsenosides co-treated with astragaloside A] results in decreased secretion of TNF protein; nobiletin inhibits the reaction [Acetaminophen results in increased expression of TNF protein] CTD PMID:31777137 PMID:32344236 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link
G Trib3 tribbles pseudokinase 3 increases expression ISO
EXP
nobiletin results in increased expression of TRIB3 mRNA CTD PMID:23321314 NCBI chr 3:140,809,634...140,815,230
Ensembl chr 3:140,809,043...140,814,497
JBrowse link
G Txnip thioredoxin interacting protein decreases expression ISO
EXP
nobiletin results in decreased expression of TXNIP mRNA; nobiletin results in decreased expression of TXNIP protein CTD PMID:23321314 NCBI chr 2:184,093,079...184,096,882
Ensembl chr 2:184,092,991...184,096,886
JBrowse link

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  CHEBI ontology 19808
    role 19757
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            antineoplastic agent 17315
              nobiletin 44
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  CHEBI ontology 19808
    subatomic particle 19807
      composite particle 19807
        hadron 19807
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            nucleon 19807
              atomic nucleus 19807
                atom 19807
                  main group element atom 19704
                    p-block element atom 19704
                      carbon group element atom 19626
                        carbon atom 19616
                          organic molecular entity 19616
                            organic molecule 19556
                              organic cyclic compound 19347
                                organic heterocyclic compound 18580
                                  oxacycle 17586
                                    benzopyran 10409
                                      1-benzopyran 10135
                                        flavonoid 6515
                                          flavones 4203
                                            methoxyflavone 425
                                              nobiletin 44
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