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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:tangeretin
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Accession:CHEBI:9400 term browser browse the term
Definition:A pentamethoxyflavone flavone with methoxy groups at positions 4', 5, 6 , 7 and 8.
Synonyms:exact_synonym: 5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one
 related_synonym: 4',5,6,7,8-pentamethoxyflavone;   5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one;   Formula=C20H20O7;   InChI=1S/C20H20O7/c1-22-12-8-6-11(7-9-12)14-10-13(21)15-16(23-2)18(24-3)20(26-5)19(25-4)17(15)27-14/h6-10H,1-5H3;   InChIKey=ULSUXBXHSYSGDT-UHFFFAOYSA-N;   SMILES=COc1ccc(cc1)-c1cc(=O)c2c(OC)c(OC)c(OC)c(OC)c2o1;   tangeritin
 xref: CAS:481-53-8;   HMDB:HMDB0030539;   KEGG:C10190;   KNApSAcK:C00001105;   LINCS:LSM-2548;   LIPID_MAPS_instance:LMPK12111443
 xref_mesh: MESH:C059006
 xref: PMID:22476082;   PMID:22585555;   PMID:22850615;   PMID:23137376;   PMID:23254473;   PMID:23265538;   Patent:CN101947215;   Patent:CN102344429;   Reaxys:351695;   Wikipedia:Tangeritin


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tangeretin 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 decreases activity
multiple interactions
increases activity
decreases expression		 ISO tangeretin results in decreased activity of ABCB1 protein
tangeretin inhibits the reaction [ABCB1 protein results in decreased uptake of Daunorubicin]; tangeretin inhibits the reaction [ABCB1 protein results in decreased uptake of Rhodamine 123]; tangeretin inhibits the reaction [ABCB1 protein results in increased transport of Digoxin]; tangeretin inhibits the reaction [Elacridar inhibits the reaction [ABCB1 protein results in decreased uptake of Rhodamine 123]]; Verapamil inhibits the reaction [tangeretin results in increased activity of ABCB1 protein]
tangeretin results in decreased expression of ABCB1 protein		 CTD PMID:30790579 PMID:34217736 NCBI chr 4:25,357,467...25,529,941
Ensembl chr 4:25,158,362...25,442,709 		JBrowse link
G Agtr1b angiotensin II receptor, type 1b multiple interactions EXP tangeretin inhibits the reaction [NG-Nitroarginine Methyl Ester results in increased expression of AGTR1B protein] CTD PMID:32479886 NCBI chr 2:102,844,969...102,920,232
Ensembl chr 2:102,844,969...102,920,232 		JBrowse link
G Casp3 caspase 3 multiple interactions EXP
ISO		 tangeretin inhibits the reaction [Cisplatin results in increased expression of CASP3 protein]
AGN 193109 inhibits the reaction [tangeretin results in decreased expression of and results in increased cleavage of CASP3 protein]; tangeretin results in decreased expression of and results in increased cleavage of CASP3 protein		 CTD PMID:27616468 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 [tangeretin 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 [tangeretin results in decreased expression of and results in increased cleavage of CASP9 protein]; tangeretin 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 Cat catalase multiple interactions EXP tangeretin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in decreased activity of CAT protein] CTD PMID:24995432 NCBI chr 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478 		JBrowse link
G Cyb5a cytochrome b5 type A multiple interactions EXP tangeretin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in increased expression of CYB5A protein] CTD PMID:24995432 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 Cybb cytochrome b-245 beta chain multiple interactions EXP tangeretin inhibits the reaction [NG-Nitroarginine Methyl Ester results in increased expression of CYBB protein] CTD PMID:32479886 NCBI chr  X:13,358,101...13,392,570
Ensembl chr  X:13,359,430...13,392,586 		JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 multiple interactions
increases metabolic processing
increases expression		 ISO tangeretin inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of CYP1A1 mRNA]; tangeretin inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of CYP1A1 protein]
CYP1A1 protein results in increased metabolism of tangeretin
tangeretin results in increased expression of CYP1A1 protein		 CTD PMID:17090139 PMID:29626627 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 multiple interactions
increases metabolic processing		 ISO tangeretin inhibits the reaction [Tetrachlorodibenzodioxin results in increased expression of CYP1A2 mRNA]
CYP1A2 protein results in increased metabolism of tangeretin		 CTD PMID:17090139 PMID:29626627 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 metabolic processing
increases expression		 ISO CYP1B1 protein results in increased metabolism of tangeretin
tangeretin results in increased expression of CYP1B1 protein		 CTD PMID:29626627 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 tangeretin results in increased activity of CYP3A4 protein
[[tangeretin results in increased activity of CYP3A4 protein] which results in increased metabolism of Midazolam] which results in increased chemical synthesis of 1-hydroxymethylmidazolam; [tangeretin 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 Dnmt1 DNA methyltransferase 1 decreases expression ISO tangeretin metabolite results in decreased expression of DNMT1 protein; tangeretin results in decreased expression of DNMT1 protein CTD PMID:37517432 NCBI chr 8:19,440,611...19,486,659
Ensembl chr 8:19,440,611...19,486,659 		JBrowse link
G Dnmt3a DNA methyltransferase 3 alpha decreases expression ISO tangeretin metabolite results in decreased expression of DNMT3A protein; tangeretin results in decreased expression of DNMT3A protein CTD PMID:37517432 NCBI chr 6:26,791,517...26,902,161
Ensembl chr 6:26,822,609...26,896,687 		JBrowse link
G Dnmt3b DNA methyltransferase 3 beta decreases expression ISO tangeretin metabolite results in decreased expression of DNMT3B protein; tangeretin results in decreased expression of DNMT3B protein CTD PMID:37517432 NCBI chr 3:142,130,588...142,169,128
Ensembl chr 3:142,130,592...142,169,124 		JBrowse link
G Gsr glutathione-disulfide reductase multiple interactions EXP tangeretin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in decreased activity of GSR protein] CTD PMID:24995432 NCBI chr16:58,482,209...58,525,256
Ensembl chr16:58,482,505...58,525,661 		JBrowse link
G Hdac1 histone deacetylase 1 decreases expression ISO tangeretin metabolite results in decreased expression of HDAC1 protein; tangeretin results in decreased expression of HDAC1 protein CTD PMID:37517432 NCBI chr 5:141,853,992...141,881,057
Ensembl chr 5:141,853,989...141,881,111 		JBrowse link
G Hdac2 histone deacetylase 2 decreases expression ISO tangeretin metabolite results in decreased expression of HDAC2 protein; tangeretin results in decreased expression of HDAC2 protein CTD PMID:37517432 NCBI chr20:40,548,244...40,571,609
Ensembl chr20:40,548,250...40,571,609 		JBrowse link
G Hdac3 histone deacetylase 3 decreases expression ISO tangeretin metabolite results in decreased expression of HDAC3 protein; tangeretin results in decreased expression of HDAC3 protein CTD PMID:37517432 NCBI chr18:29,770,637...29,789,850
Ensembl chr18:29,770,636...29,793,856 		JBrowse link
G Hdac4 histone deacetylase 4 decreases expression ISO tangeretin metabolite results in decreased expression of HDAC4 protein; tangeretin results in decreased expression of HDAC4 protein CTD PMID:37517432 NCBI chr 9:92,503,467...92,750,164
Ensembl chr 9:92,507,611...92,750,164 		JBrowse link
G Hdac8 histone deacetylase 8 decreases expression ISO tangeretin metabolite results in decreased expression of HDAC8 protein; tangeretin results in decreased expression of HDAC8 protein CTD PMID:37517432 NCBI chr  X:67,385,288...67,593,014
Ensembl chr  X:67,385,289...67,592,923 		JBrowse link
G Hmox1 heme oxygenase 1 multiple interactions
increases expression		 EXP
ISO		 tangeretin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in decreased expression of HMOX1 mRNA]; tangeretin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in decreased expression of HMOX1 protein]
tangeretin metabolite results in increased expression of HMOX1 mRNA; tangeretin metabolite results in increased expression of HMOX1 protein; tangeretin results in increased expression of HMOX1 mRNA; tangeretin results in increased expression of HMOX1 protein		 CTD PMID:24995432 PMID:37517432 NCBI chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079 		JBrowse link
G Il10 interleukin 10 multiple interactions EXP tangeretin inhibits the reaction [Cisplatin results in decreased expression of IL10 protein] CTD PMID:27616468 NCBI chr13:42,472,625...42,477,308
Ensembl chr13:42,472,839...42,477,313 		JBrowse link
G Il1b interleukin 1 beta multiple interactions EXP tangeretin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in increased expression of IL1B protein] CTD PMID:24995432 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 tangeretin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in increased expression of IL6 protein] CTD PMID:24995432 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178 		JBrowse link
G Keap1 Kelch-like ECH-associated protein 1 multiple interactions EXP tangeretin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in increased expression of KEAP1 mRNA]; tangeretin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in increased expression of KEAP1 protein] CTD PMID:24995432 NCBI chr 8:19,768,375...19,777,862
Ensembl chr 8:19,768,375...19,777,862 		JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 2 multiple interactions
decreases methylation
increases expression		 EXP
ISO		 tangeretin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in decreased expression of NFE2L2 mRNA]; tangeretin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in decreased expression of NFE2L2 protein]; tangeretin inhibits the reaction [Cisplatin results in increased expression of NFE2L2 protein]
tangeretin metabolite results in decreased methylation of NFE2L2 promoter; tangeretin results in decreased methylation of NFE2L2 promoter
tangeretin metabolite results in increased expression of NFE2L2 mRNA; tangeretin metabolite results in increased expression of NFE2L2 protein; tangeretin results in increased expression of NFE2L2 mRNA; tangeretin results in increased expression of NFE2L2 protein		 CTD PMID:24995432 PMID:27616468 PMID:37517432 NCBI chr 3:60,594,239...60,621,712
Ensembl chr 3:60,594,242...60,621,737 		JBrowse link
G Nos2 nitric oxide synthase 2 multiple interactions EXP tangeretin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in increased expression of NOS2 protein]; tangeretin inhibits the reaction [Cisplatin results in increased expression of NOS2 protein] CTD PMID:24995432 PMID:27616468 NCBI chr10:63,815,308...63,851,208
Ensembl chr10:63,815,308...63,851,210 		JBrowse link
G Nos3 nitric oxide synthase 3 multiple interactions EXP tangeretin inhibits the reaction [NG-Nitroarginine Methyl Ester results in decreased expression of NOS3 protein] CTD PMID:32479886 NCBI chr 4:10,793,834...10,814,170
Ensembl chr 4:10,793,834...10,814,166 		JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 multiple interactions
increases expression		 EXP
ISO		 tangeretin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in decreased expression of NQO1 mRNA]; tangeretin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in decreased expression of NQO1 protein]
tangeretin metabolite results in increased expression of NQO1 mRNA; tangeretin metabolite results in increased expression of NQO1 protein; tangeretin results in increased expression of NQO1 mRNA; tangeretin results in increased expression of NQO1 protein		 CTD PMID:24995432 PMID:37517432 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 multiple interactions ISO AGN 193109 inhibits the reaction [tangeretin results in decreased expression of and results in increased cleavage of PARP1 protein]; tangeretin 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 Pkm pyruvate kinase M1/2 increases activity ISO tangeretin results in increased activity of PKM protein CTD PMID:25388478 NCBI chr 8:60,057,629...60,079,600
Ensembl chr 8:60,057,402...60,079,599 		JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions EXP tangeretin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in increased expression of PTGS2 protein] CTD PMID:24995432 NCBI chr13:62,163,936...62,172,193
Ensembl chr13:62,163,932...62,172,188 		JBrowse link
G Rarb retinoic acid receptor, beta increases expression
multiple interactions		 ISO tangeretin results in increased expression of RARB mRNA; tangeretin results in increased expression of RARB protein
AGN 193109 inhibits the reaction [tangeretin 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 Rela RELA proto-oncogene, NF-kB subunit multiple interactions EXP tangeretin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in increased expression of RELA mRNA]; tangeretin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in increased expression of RELA protein]; tangeretin inhibits the reaction [Cisplatin results in increased expression of RELA protein] CTD PMID:24995432 PMID:27616468 NCBI chr 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484 		JBrowse link
G Star steroidogenic acute regulatory protein multiple interactions EXP tangeretin inhibits the reaction [NG-Nitroarginine Methyl Ester results in decreased expression of STAR protein] CTD PMID:32479886 NCBI chr16:66,267,094...66,274,368
Ensembl chr16:66,264,807...66,271,672 		JBrowse link
G Tnf tumor necrosis factor multiple interactions EXP tangeretin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in increased expression of TNF mRNA]; tangeretin inhibits the reaction [9,10-Dimethyl-1,2-benzanthracene results in increased expression of TNF protein]; tangeretin inhibits the reaction [Cisplatin results in increased expression of TNF protein] CTD PMID:24995432 PMID:27616468 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629 		JBrowse link
G Ugt1a1 UDP glucuronosyltransferase family 1 member A1 increases expression ISO tangeretin metabolite results in increased expression of UGT1A1 mRNA; tangeretin metabolite results in increased expression of UGT1A1 protein; tangeretin results in increased expression of UGT1A1 mRNA; tangeretin results in increased expression of UGT1A1 protein CTD PMID:37517432 NCBI chr 9:88,801,344...88,808,465
Ensembl chr 9:88,713,184...88,808,465 		JBrowse link
gardenin B term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Bcl2 BCL2, apoptosis regulator decreases expression ISO gardenin B results in decreased expression of BCL2 protein CTD PMID:27423764 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 Casp2 caspase 2 multiple interactions ISO gardenin B results in increased cleavage of and results in increased activity of CASP2 protein CTD PMID:27423764 NCBI chr 4:71,149,632...71,167,388
Ensembl chr 4:71,149,669...71,167,379 		JBrowse link
G Casp3 caspase 3 multiple interactions ISO gardenin B results in increased cleavage of and results in increased activity of CASP3 protein CTD PMID:27423764 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Casp8 caspase 8 multiple interactions ISO gardenin B results in increased cleavage of and results in increased activity of CASP8 protein CTD PMID:27423764 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 gardenin B results in increased cleavage of and results in increased activity of CASP9 protein CTD PMID:27423764 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626 		JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 increases cleavage ISO gardenin B results in increased cleavage of PARP1 protein CTD PMID:27423764 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404 		JBrowse link
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  CHEBI ontology 19880
    role 19850
      application 19695
        pharmaceutical 19532
          drug 19532
            antineoplastic agent 17823
              tangeretin 40
                gardenin B 6
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  CHEBI ontology 19880
    subatomic particle 19878
      composite particle 19878
        hadron 19878
          baryon 19878
            nucleon 19878
              atomic nucleus 19878
                atom 19878
                  main group element atom 19817
                    p-block element atom 19817
                      carbon group element atom 19757
                        carbon atom 19754
                          organic molecular entity 19754
                            organic molecule 19706
                              organic cyclic compound 19495
                                organic heterocyclic compound 18874
                                  oxacycle 17906
                                    benzopyran 11972
                                      1-benzopyran 11726
                                        flavonoid 7226
                                          anthoxanthin 4585
                                            flavones 4585
                                              methoxyflavone 493
                                                pentamethoxyflavone 42
                                                  tangeretin 40
                                                    gardenin B 6
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