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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:miquelianin
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Accession:CHEBI:66395 term browser browse the term
Definition:A quercetin O-glycoside that consists of quercetin attached to a beta-D-glucuronopyranosyl moiety at position 3 via a glycosidic linkage. Isolated from Salvia and Phaseolus vulgaris, it exhibits antioxidant and antidepressant activities.
Synonyms:exact_synonym: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl beta-D-glucopyranosiduronic acid
 related_synonym: Formula=C21H18O13;   InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-25,27-29H,(H,30,31)/t14-,15-,16+,19-,21+/m0/s1;   InChIKey=DUBCCGAQYVUYEU-ZUGPOPFOSA-N;   SMILES=O[C@H]1[C@@H](O[C@@H]([C@@H](O)[C@@H]1O)C(O)=O)Oc1c(oc2cc(O)cc(O)c2c1=O)-c1ccc(O)c(O)c1;   quercetin 3-O-glucuronide;   quercetin-3-O-beta-D-glucuronopyranoside;   quercetin-3-O-glucoronoside;   quercituron
 alt_id: MESH:C443401
 xref: CAS:22688-79-5;   HMDB:HMDB0029212;   LIPID_MAPS_instance:LMPK12112173
 xref_mesh: MESH:C443401
 xref: PMID:10479312;   PMID:11809447;   PMID:14735439;   PMID:15742803;   PMID:16521111;   PMID:18618463;   Reaxys:72004;   Wikipedia:Miquelianin



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miquelianin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Acadm acyl-CoA dehydrogenase medium chain multiple interactions EXP quercetin 3-O-glucuronide inhibits the reaction [[Oleic Acid co-treated with Palmitic Acid] results in decreased expression of ACADM mRNA] CTD PMID:26190035 NCBI chr 2:242,858,865...242,883,036
Ensembl chr 2:242,858,865...242,883,147
JBrowse link
G Adrb2 adrenoceptor beta 2 multiple interactions ISO quercetin 3-O-glucuronide inhibits the reaction [Norepinephrine binds to ADRB2 protein] CTD PMID:24929186 NCBI chr18:55,642,459...55,644,501
Ensembl chr18:55,502,903...55,644,512
JBrowse link
G Agt angiotensinogen multiple interactions ISO quercetin 3-O-glucuronide analog inhibits the reaction [AGT protein results in increased phosphorylation of JUN protein] CTD PMID:12054679 NCBI chr19:52,529,139...52,549,618
Ensembl chr19:52,529,185...52,540,977
JBrowse link
G Alox5 arachidonate 5-lipoxygenase multiple interactions ISO quercetin 3-O-glucuronide inhibits the reaction [ALOX5 protein results in increased chemical synthesis of Leukotriene B4] CTD PMID:18096136 NCBI chr 4:149,531,329...149,578,696
Ensembl chr 4:149,531,515...149,578,743
JBrowse link
G App amyloid beta precursor protein multiple interactions
decreases expression
ISO quercetin 3-O-glucuronide inhibits the reaction [APP protein binds to APP protein modified form]
quercetin 3-O-glucuronide results in decreased expression of APP protein
CTD PMID:23097297 NCBI chr11:24,019,774...24,236,584
Ensembl chr11:24,019,778...24,236,561
JBrowse link
G Cat catalase multiple interactions EXP [quercetin 3-O-glucuronide co-treated with 3-methylquercetin co-treated with Quercetin] results in increased expression of CAT mRNA; [quercetin 3-O-glucuronide co-treated with 3-methylquercetin co-treated with Quercetin] results in increased expression of CAT protein CTD PMID:25716194 NCBI chr 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478
JBrowse link
G Cav1 caveolin 1 multiple interactions ISO quercetin 3-O-glucuronide inhibits the reaction [Lysophosphatidylcholines results in increased expression of CAV1 mRNA] CTD PMID:27257344 NCBI chr 4:45,640,624...45,673,708
Ensembl chr 4:45,634,918...45,673,705
JBrowse link
G Cd36 CD36 molecule decreases expression ISO quercetin 3-O-glucuronide results in decreased expression of CD36 mRNA CTD PMID:18199750 NCBI chr 4:17,317,343...17,410,084
Ensembl chr 4:17,354,466...17,513,903
JBrowse link
G Cpt1a carnitine palmitoyltransferase 1A multiple interactions EXP quercetin 3-O-glucuronide inhibits the reaction [[Oleic Acid co-treated with Palmitic Acid] results in decreased expression of CPT1A mRNA] CTD PMID:26190035 NCBI chr 1:200,564,634...200,627,059
Ensembl chr 1:200,565,613...200,627,055
JBrowse link
G Fas Fas cell surface death receptor multiple interactions EXP quercetin 3-O-glucuronide inhibits the reaction [[Oleic Acid co-treated with Palmitic Acid] results in increased expression of FAS mRNA]; quercetin 3-O-glucuronide inhibits the reaction [Dietary Fats results in increased expression of FAS mRNA] CTD PMID:26190035 NCBI chr 1:231,798,963...231,832,591
Ensembl chr 1:231,798,960...231,832,591
JBrowse link
G Gclc glutamate-cysteine ligase, catalytic subunit multiple interactions EXP [quercetin 3-O-glucuronide co-treated with 3-methylquercetin co-treated with Quercetin] results in increased expression of GCLC mRNA; [quercetin 3-O-glucuronide co-treated with 3-methylquercetin co-treated with Quercetin] results in increased expression of GCLC protein CTD PMID:25716194 NCBI chr 8:78,629,899...78,668,547
Ensembl chr 8:78,630,127...78,668,544
JBrowse link
G Hmox1 heme oxygenase 1 multiple interactions ISO
EXP
quercetin 3-O-glucuronide inhibits the reaction [Norepinephrine results in increased expression of HMOX1 mRNA]
[quercetin 3-O-glucuronide co-treated with 3-methylquercetin co-treated with Quercetin] results in increased expression of HMOX1 mRNA; [quercetin 3-O-glucuronide co-treated with 3-methylquercetin co-treated with Quercetin] results in increased expression of HMOX1 protein
CTD PMID:24929186 PMID:25716194 NCBI chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079
JBrowse link
G Icam1 intercellular adhesion molecule 1 multiple interactions ISO quercetin 3-O-glucuronide inhibits the reaction [Lysophosphatidylcholines results in increased expression of ICAM1 mRNA] CTD PMID:27257344 NCBI chr 8:19,553,063...19,565,438
Ensembl chr 8:19,553,645...19,565,438
JBrowse link
G Ikbkb inhibitor of nuclear factor kappa B kinase subunit beta multiple interactions ISO quercetin 3-O-glucuronide inhibits the reaction [Palmitates results in increased phosphorylation of IKBKB protein] CTD PMID:23504962 NCBI chr16:69,319,487...69,373,251
Ensembl chr16:69,319,554...69,373,250
JBrowse link
G Il1b interleukin 1 beta multiple interactions EXP quercetin 3-O-glucuronide inhibits the reaction [[Oleic Acid co-treated with Palmitic Acid] results in increased expression of IL1B protein] CTD PMID:26190035 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 quercetin 3-O-glucuronide inhibits the reaction [Palmitates results in increased secretion of IL6 protein] CTD PMID:23504962 NCBI chr 4:5,214,602...5,219,178
Ensembl chr 4:5,213,394...5,219,178
JBrowse link
G Ins2 insulin 2 multiple interactions ISO quercetin 3-O-glucuronide inhibits the reaction [Palmitates inhibits the reaction [INS protein results in increased chemical synthesis of Nitric Oxide]]; quercetin 3-O-glucuronide inhibits the reaction [Palmitates inhibits the reaction [INS protein results in increased phosphorylation of IRS1 protein]]; quercetin 3-O-glucuronide inhibits the reaction [Palmitates inhibits the reaction [INS protein results in increased phosphorylation of NOS3 protein]] CTD PMID:23504962 NCBI chr 1:197,843,277...197,992,522
Ensembl chr 1:197,843,281...197,864,775
JBrowse link
G Irs1 insulin receptor substrate 1 multiple interactions ISO quercetin 3-O-glucuronide inhibits the reaction [Palmitates inhibits the reaction [INS protein results in increased phosphorylation of IRS1 protein]]; quercetin 3-O-glucuronide inhibits the reaction [Palmitates results in increased phosphorylation of IRS1 protein] CTD PMID:23504962 NCBI chr 9:83,552,964...83,605,797
Ensembl chr 9:83,548,944...83,606,122
JBrowse link
G Jun Jun proto-oncogene, AP-1 transcription factor subunit multiple interactions ISO quercetin 3-O-glucuronide analog inhibits the reaction [AGT protein results in increased phosphorylation of JUN protein] CTD PMID:12054679 NCBI chr 5:109,894,175...109,897,268
Ensembl chr 5:109,893,145...109,897,656
JBrowse link
G Mmp2 matrix metallopeptidase 2 multiple interactions ISO quercetin 3-O-glucuronide inhibits the reaction [Norepinephrine results in increased expression of MMP2 mRNA] CTD PMID:24929186 NCBI chr19:14,154,657...14,182,870
Ensembl chr19:14,154,657...14,182,870
JBrowse link
G Mmp9 matrix metallopeptidase 9 multiple interactions ISO quercetin 3-O-glucuronide inhibits the reaction [Norepinephrine results in increased activity of MMP9 protein]; quercetin 3-O-glucuronide inhibits the reaction [Norepinephrine results in increased expression of MMP9 mRNA] CTD PMID:24929186 NCBI chr 3:153,684,158...153,692,118
Ensembl chr 3:153,683,858...153,692,120
JBrowse link
G Msr1 macrophage scavenger receptor 1 decreases expression ISO quercetin 3-O-glucuronide results in decreased expression of MSR1 mRNA CTD PMID:18199750 NCBI chr16:52,717,775...52,802,890
Ensembl chr16:52,717,732...52,799,676
JBrowse link
G Nos2 nitric oxide synthase 2 multiple interactions ISO quercetin 3-O-glucuronide inhibits the reaction [lipopolysaccharide, E coli O55-B5 results in increased expression of NOS2 protein] CTD PMID:27257013 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 ISO quercetin 3-O-glucuronide inhibits the reaction [Palmitates inhibits the reaction [INS protein results in increased phosphorylation of NOS3 protein]] CTD PMID:23504962 NCBI chr 4:10,793,834...10,814,170
Ensembl chr 4:10,793,834...10,814,166
JBrowse link
G Ppara peroxisome proliferator activated receptor alpha multiple interactions EXP quercetin 3-O-glucuronide inhibits the reaction [[Oleic Acid co-treated with Palmitic Acid] results in decreased expression of PPARA mRNA]; quercetin 3-O-glucuronide inhibits the reaction [[Oleic Acid co-treated with Palmitic Acid] results in decreased expression of PPARA protein]; quercetin 3-O-glucuronide inhibits the reaction [Dietary Fats results in decreased expression of PPARA protein] CTD PMID:26190035 NCBI chr 7:116,832,405...116,900,878
Ensembl chr 7:116,832,756...116,895,346
JBrowse link
G Pparg peroxisome proliferator-activated receptor gamma increases expression ISO quercetin 3-O-glucuronide results in increased expression of PPARG mRNA CTD PMID:25765892 NCBI chr 4:148,423,102...148,548,471
Ensembl chr 4:148,423,194...148,548,468
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions ISO quercetin 3-O-glucuronide inhibits the reaction [lipopolysaccharide, E coli O55-B5 results in increased expression of PTGS2 protein] CTD PMID:27257013 NCBI chr13:62,164,080...62,169,770
Ensembl chr13:62,163,932...62,172,188
JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions ISO quercetin 3-O-glucuronide inhibits the reaction [Palmitates results in increased phosphorylation of RELA protein] CTD PMID:23504962 NCBI chr 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484
JBrowse link
G Slc22a8 solute carrier family 22 member 8 multiple interactions
increases uptake
ISO quercetin 3-O-glucuronide analog inhibits the reaction [SLC22A8 protein results in increased transport of 4-carboxyfluorescein]; quercetin 3-O-glucuronide inhibits the reaction [SLC22A8 protein results in increased transport of 4-carboxyfluorescein]
SLC22A8 protein results in increased uptake of quercetin 3-O-glucuronide analog
CTD PMID:21244849 NCBI chr 1:205,496,331...205,516,378
Ensembl chr 1:205,498,084...205,517,450
JBrowse link
G Srebf1 sterol regulatory element binding transcription factor 1 multiple interactions EXP quercetin 3-O-glucuronide inhibits the reaction [[Oleic Acid co-treated with Palmitic Acid] results in increased expression of SREBF1 mRNA]; quercetin 3-O-glucuronide inhibits the reaction [Dietary Fats results in increased expression of SREBF1 mRNA] CTD PMID:26190035 NCBI chr10:45,007,637...45,029,650
Ensembl chr10:45,007,637...45,029,650
JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO
EXP
quercetin 3-O-glucuronide inhibits the reaction [[lipopolysaccharide, E coli O55-B5 co-treated with TNF protein] results in increased expression of VCAM1 protein]; quercetin 3-O-glucuronide inhibits the reaction [Palmitates results in increased secretion of TNF protein]
quercetin 3-O-glucuronide inhibits the reaction [[Oleic Acid co-treated with Palmitic Acid] results in increased expression of TNF protein]
CTD PMID:17880982 PMID:23504962 PMID:26190035 NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
JBrowse link
G Tnfsf11 TNF superfamily member 11 decreases activity ISO quercetin 3-O-glucuronide results in decreased activity of TNFSF11 protein CTD PMID:19495926 NCBI chr15:53,674,990...53,705,171
Ensembl chr15:53,673,877...53,705,445
JBrowse link
G Vcam1 vascular cell adhesion molecule 1 multiple interactions ISO quercetin 3-O-glucuronide inhibits the reaction [[lipopolysaccharide, E coli O55-B5 co-treated with TNF protein] results in increased expression of VCAM1 protein] CTD PMID:17880982 NCBI chr 2:204,038,120...204,057,852
Ensembl chr 2:204,038,114...204,057,958
JBrowse link

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  CHEBI ontology 20059
    role 20009
      chemical role 19539
        antioxidant 14502
          miquelianin 33
Path 2
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  CHEBI ontology 20059
    subatomic particle 20056
      composite particle 20056
        hadron 20056
          baryon 20056
            nucleon 20056
              atomic nucleus 20056
                atom 20056
                  main group element atom 19956
                    p-block element atom 19956
                      carbon group element atom 19882
                        carbon atom 19873
                          organic molecular entity 19873
                            organic molecule 19819
                              organic cyclic compound 19581
                                organic heterocyclic compound 18804
                                  oxacycle 17704
                                    benzopyran 11204
                                      1-benzopyran 10945
                                        flavonoid 6568
                                          flavones 4216
                                            hydroxyflavone 4204
                                              flavonols 4109
                                                7-hydroxyflavonol 4087
                                                  quercetin 4034
                                                    quercetin O-glycoside 458
                                                      miquelianin 33
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