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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 4:26,312,403...26,488,456
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 chr10:1,022,041...1,162,431
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 6:137,534,810...137,555,131
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 4:36,752,061...36,769,970
Ensembl chr 4:35,785,237...35,803,423
JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions ISO
EXP
nobiletin inhibits the reaction [Hydrogen Peroxide results in increased expression of BAX protein]
nobiletin inhibits the reaction [Arsenic results in increased expression of BAX protein]; nobiletin inhibits the reaction [nonylphenol results in increased expression of BAX mRNA]
CTD PMID:29687528 PMID:32815738 PMID:36850985 NCBI chr 1:105,076,472...105,081,906
Ensembl chr 1:95,938,808...95,945,368
JBrowse link
G Bcl2 BCL2, apoptosis regulator multiple interactions ISO
EXP
nobiletin inhibits the reaction [Hydrogen Peroxide results in decreased expression of BCL2 protein]
nobiletin inhibits the reaction [Arsenic results in decreased expression of BCL2 protein]; nobiletin inhibits the reaction [nonylphenol results in decreased expression of BCL2 mRNA]
CTD PMID:29687528 PMID:32815738 PMID:36850985 NCBI chr13:23,204,464...23,366,900
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
EXP
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
nobiletin inhibits the reaction [Arsenic results in increased expression of CASP3 protein]; nobiletin inhibits the reaction [nonylphenol results in increased expression of CASP3 mRNA]
CTD PMID:32815738 PMID:33058988 PMID:36850985 NCBI chr16:52,395,539...52,413,794
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 9:67,747,109...67,806,699
Ensembl chr 9:60,264,075...60,312,542
JBrowse link
G Casp9 caspase 9 multiple interactions ISO
EXP
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
nobiletin inhibits the reaction [Arsenic results in increased expression of CASP9 protein]
CTD PMID:33058988 PMID:36850985 Ensembl chr 5:154,109,046...154,126,626 JBrowse link
G Cat catalase multiple interactions EXP nobiletin inhibits the reaction [Arsenic results in decreased activity of CAT protein]; nobiletin inhibits the reaction [nonylphenol results in decreased activity of CAT protein] CTD PMID:32815738 PMID:36850985 NCBI chr 3:110,297,340...110,329,526
Ensembl chr 3:89,842,399...89,874,478
JBrowse link
G Ccna2 cyclin A2 decreases expression ISO
EXP
nobiletin results in decreased expression of CCNA2 mRNA CTD PMID:23321314 NCBI chr 2:121,355,363...121,361,762
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 5:29,082,169...29,094,879
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 chr18:56,527,071...56,536,406
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 8:66,991,940...66,998,014
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 8:66,971,261...66,978,149
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 6:21,093,927...21,103,091
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 chr12:14,321,771...14,343,886
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 7:65,001,695...65,006,517
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 2:251,343,250...251,376,709
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 1:107,701,985...107,720,538
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 chr14:95,378,626...95,551,358
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 6:110,852,188...110,855,054
Ensembl chr 6:105,121,170...105,124,036
JBrowse link
G Fshb follicle stimulating hormone subunit beta multiple interactions EXP nobiletin inhibits the reaction [nonylphenol results in decreased expression of FSHB protein] CTD PMID:32815738 NCBI chr 3:114,003,262...114,007,072
Ensembl chr 3:93,548,560...93,552,370
JBrowse link
G Gpt glutamic--pyruvic transaminase multiple interactions EXP nobiletin inhibits the reaction [Acetaminophen results in increased expression of GPT protein]; nobiletin inhibits the reaction [Arsenic results in increased expression of GPT protein] CTD PMID:31777137 PMID:36850985 NCBI chr 7:110,295,599...110,300,134
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 3:28,501,836...28,528,754
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 chr10:6,136,458...6,560,003
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 4:170,297,811...170,775,420
Ensembl chr 4:168,599,546...169,042,279
JBrowse link
G Gsr glutathione-disulfide reductase multiple interactions EXP nobiletin inhibits the reaction [Arsenic results in decreased activity of GSR protein]; nobiletin inhibits the reaction [nonylphenol results in decreased activity of GSR protein] CTD PMID:32815738 PMID:36850985 NCBI chr16:65,185,574...65,228,742
Ensembl chr16:58,482,505...58,525,661
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 chr17:47,421,875...47,422,905
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 chr19:13,452,365...13,479,823
Ensembl chr19:13,467,244...13,474,079
JBrowse link
G Hsd17b3 hydroxysteroid (17-beta) dehydrogenase 3 multiple interactions EXP nobiletin inhibits the reaction [nonylphenol results in decreased expression of HSD17B3 mRNA] CTD PMID:32815738 NCBI chr17:1,032,958...1,064,283
Ensembl chr17:1,027,229...1,058,554
JBrowse link
G Hsd3b1 hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 1 multiple interactions EXP nobiletin inhibits the reaction [nonylphenol results in decreased expression of HSD3B1 mRNA] CTD PMID:32815738 NCBI chr 2:188,858,574...188,864,694
Ensembl chr 2:186,169,863...186,175,999
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]; nobiletin inhibits the reaction [Arsenic results in increased expression of IL1B protein] CTD PMID:31777137 PMID:32344236 PMID:36850985 NCBI chr 3:137,030,200...137,036,581
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]; nobiletin inhibits the reaction [Arsenic results in increased expression of IL6 protein] CTD PMID:31777137 PMID:32344236 PMID:36850985 NCBI chr 4:5,889,999...5,894,575
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 1:244,494,916...244,589,250
Ensembl chr 1:235,124,316...235,176,766
JBrowse link
G Lhb luteinizing hormone subunit beta multiple interactions EXP nobiletin inhibits the reaction [nonylphenol results in decreased expression of LHB protein] CTD PMID:32815738 NCBI chr 1:105,037,457...105,038,446
Ensembl chr 1:95,900,984...95,901,972
Ensembl chr 1:95,900,984...95,901,972
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 8:13,133,043...13,140,761
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 3:174,103,474...174,111,434
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 5:164,167,985...164,277,438
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 1:206,293,717...206,326,006
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 3:81,001,529...81,031,165
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 chr13:94,839,484...94,871,295
Ensembl chr13:92,307,586...92,339,404
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions EXP nobiletin inhibits the reaction [Arsenic results in increased expression of PTGS2 protein] CTD PMID:36850985 NCBI chr13:64,714,063...64,722,320
Ensembl chr13:62,163,932...62,172,188
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 chr15:10,837,252...11,482,037
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 5:138,002,522...138,030,742
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 5:136,660,022...136,694,173
Ensembl chr 5:131,374,542...131,408,728
JBrowse link
G Star steroidogenic acute regulatory protein multiple interactions EXP nobiletin inhibits the reaction [nonylphenol results in decreased expression of STAR mRNA] CTD PMID:32815738 NCBI chr16:72,969,824...72,974,447
Ensembl chr16:66,264,807...66,271,672
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:3,766,509...3,772,578
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 chr12:40,681,346...40,750,106
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]; nobiletin inhibits the reaction [Arsenic results in increased expression of TNF protein] CTD PMID:31777137 PMID:32344236 PMID:36850985 NCBI chr20:3,626,685...3,629,303
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 3:161,269,939...161,275,533
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 2:186,781,933...186,785,736
Ensembl chr 2:184,092,991...184,096,886
JBrowse link

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  CHEBI ontology 19909
    role 19880
      application 19720
        pharmaceutical 19558
          drug 19558
            antineoplastic agent 17846
              nobiletin 53
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  CHEBI ontology 19909
    subatomic particle 19907
      composite particle 19907
        hadron 19907
          baryon 19907
            nucleon 19907
              atomic nucleus 19907
                atom 19907
                  main group element atom 19846
                    p-block element atom 19846
                      carbon group element atom 19784
                        carbon atom 19781
                          organic molecular entity 19781
                            organic molecule 19735
                              organic cyclic compound 19528
                                organic heterocyclic compound 18895
                                  oxacycle 17921
                                    benzopyran 11992
                                      1-benzopyran 11746
                                        flavonoid 7235
                                          anthoxanthin 4588
                                            flavones 4588
                                              methoxyflavone 500
                                                nobiletin 53
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