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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
Ensembl chr13:22,684,989...22,853,743
Ensembl chr13:22,684,989...22,853,743
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
multiple interactions
increases expression
ISO CYP1A1 protein results in increased metabolism of nobiletin
nobiletin inhibits the reaction [DDT results in increased expression of CYP1A1 mRNA]; nobiletin inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of CYP1A1 mRNA]
nobiletin results in increased expression of CYP1A1 protein
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 chr12:9,207,978...9,230,064
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 chr14:91,176,979...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 chr10:5,629,683...6,053,262
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 chr17:42,726,132...42,727,162
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 1:196,864,336...196,896,475
Ensembl chr 1:196,864,336...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 NFE2 like bZIP transcription factor 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...60,621,712
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 Slc2a1 solute carrier family 2 member 1 multiple interactions ISO nobiletin inhibits the reaction [SLC2A1 protein results in increased uptake of 2-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxyglucose] CTD PMID:36870413 NCBI chr 5:132,717,196...132,745,416
Ensembl chr 5:132,717,196...132,745,416
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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                  main group element atom 19866
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                        carbon atom 19806
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                            organic molecule 19758
                              organic cyclic compound 19565
                                organic heterocyclic compound 18906
                                  oxacycle 17850
                                    benzopyran 11796
                                      1-benzopyran 11539
                                        flavonoid 6906
                                          anthoxanthin 4541
                                            flavones 4541
                                              methoxyflavone 478
                                                nobiletin 45
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