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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-Coenzyme A dehydrogenase, medium chain multiple interactions ISO 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 3:153,922,353...153,944,643
Ensembl chr 3:153,922,357...153,944,632
JBrowse link
G Adrb2 adrenergic receptor, beta 2 multiple interactions ISO quercetin 3-O-glucuronide inhibits the reaction [Norepinephrine binds to ADRB2 protein] CTD PMID:24929186 NCBI chr18:62,177,713...62,179,981
Ensembl chr18:62,177,816...62,179,959
JBrowse link
G Agt angiotensinogen (serpin peptidase inhibitor, clade A, member 8) 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 8:124,556,587...124,569,706
Ensembl chr 8:124,556,534...124,569,706
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 6:116,410,071...116,461,178
Ensembl chr 6:116,410,077...116,461,178
JBrowse link
G App amyloid beta (A4) 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 chr16:84,952,666...85,175,255
Ensembl chr16:84,949,685...85,173,766
JBrowse link
G Cat catalase multiple interactions ISO [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 2:103,453,904...103,485,153
Ensembl chr 2:103,453,849...103,485,160
JBrowse link
G Cav1 caveolin 1, caveolae protein multiple interactions ISO quercetin 3-O-glucuronide inhibits the reaction [Lysophosphatidylcholines results in increased expression of CAV1 mRNA] CTD PMID:27257344 NCBI chr 6:17,306,335...17,341,328
Ensembl chr 6:17,306,335...17,341,452
JBrowse link
G Cd36 CD36 molecule decreases expression EXP quercetin 3-O-glucuronide results in decreased expression of CD36 mRNA CTD PMID:18199750 NCBI chr 5:17,781,690...17,888,959
Ensembl chr 5:17,781,690...17,888,801
JBrowse link
G Cpt1a carnitine palmitoyltransferase 1a, liver multiple interactions ISO 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 chr19:3,322,326...3,385,735
Ensembl chr19:3,322,334...3,385,733
JBrowse link
G Fas Fas (TNF receptor superfamily member 6) multiple interactions ISO 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 chr19:34,290,647...34,327,775
Ensembl chr19:34,290,666...34,327,772
JBrowse link
G Gclc glutamate-cysteine ligase, catalytic subunit multiple interactions ISO [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 9:77,754,535...77,794,489
Ensembl chr 9:77,754,535...77,794,485
JBrowse link
G Hmox1 heme oxygenase 1 multiple interactions ISO 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 chr 8:75,093,618...75,100,593
Ensembl chr 8:75,093,621...75,100,589
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 9:21,015,940...21,028,814
Ensembl chr 9:21,015,985...21,028,817
JBrowse link
G Ikbkb inhibitor of kappaB kinase beta multiple interactions ISO quercetin 3-O-glucuronide inhibits the reaction [Palmitates results in increased phosphorylation of IKBKB protein] CTD PMID:23504962 NCBI chr 8:22,659,205...22,706,589
Ensembl chr 8:22,659,212...22,706,589
JBrowse link
G Il1b interleukin 1 beta multiple interactions ISO 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 2:129,364,569...129,371,164
Ensembl chr 2:129,364,570...129,371,139
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 5:30,013,114...30,019,975
Ensembl chr 5:30,013,114...30,019,981
JBrowse link
G Ins2 insulin II 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 7:142,678,656...142,679,726
Ensembl chr 7:142,678,656...142,743,381
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 1:82,233,105...82,291,439
Ensembl chr 1:82,233,112...82,235,933
Ensembl chr 1:82,233,112...82,235,933
JBrowse link
G Jun jun proto-oncogene 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 4:95,049,036...95,052,222
Ensembl chr 4:95,049,034...95,052,222
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 chr 8:92,827,290...92,853,421
Ensembl chr 8:92,827,291...92,853,420
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 2:164,940,326...164,955,850
Ensembl chr 2:164,940,780...164,955,850
JBrowse link
G Msr1 macrophage scavenger receptor 1 decreases expression EXP quercetin 3-O-glucuronide results in decreased expression of MSR1 mRNA CTD PMID:18199750 NCBI chr 8:39,543,232...39,642,750
Ensembl chr 8:39,581,685...39,642,673
JBrowse link
G Nos2 nitric oxide synthase 2, inducible multiple interactions EXP quercetin 3-O-glucuronide inhibits the reaction [lipopolysaccharide, E coli O55-B5 results in increased expression of NOS2 protein] CTD PMID:27257013 NCBI chr11:78,920,787...78,960,226
Ensembl chr11:78,920,787...78,960,254
JBrowse link
G Nos3 nitric oxide synthase 3, endothelial cell 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 5:24,364,816...24,384,474
Ensembl chr 5:24,364,810...24,384,474
JBrowse link
G Ppara peroxisome proliferator activated receptor alpha multiple interactions ISO 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 chr15:85,734,910...85,806,851
Ensembl chr15:85,734,983...85,802,819
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 6:115,360,879...115,490,404
Ensembl chr 6:115,360,951...115,490,399
JBrowse link
G Ptgs2 prostaglandin-endoperoxide synthase 2 multiple interactions EXP quercetin 3-O-glucuronide inhibits the reaction [lipopolysaccharide, E coli O55-B5 results in increased expression of PTGS2 protein] CTD PMID:27257013 NCBI chr 1:150,100,031...150,108,234
Ensembl chr 1:150,100,031...150,108,227
JBrowse link
G Rela v-rel reticuloendotheliosis viral oncogene homolog A (avian) multiple interactions ISO quercetin 3-O-glucuronide inhibits the reaction [Palmitates results in increased phosphorylation of RELA protein] CTD PMID:23504962 NCBI chr19:5,637,442...5,648,134
Ensembl chr19:5,637,483...5,648,130
JBrowse link
G Slc22a8 solute carrier family 22 (organic anion transporter), 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 chr19:8,591,254...8,611,835
Ensembl chr19:8,591,254...8,611,835
JBrowse link
G Srebf1 sterol regulatory element binding transcription factor 1 multiple interactions ISO 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 chr11:60,199,084...60,224,186
Ensembl chr11:60,199,089...60,222,581
JBrowse link
G Tnf tumor necrosis factor 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]; 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 chr17:35,199,367...35,202,007
Ensembl chr17:35,199,381...35,202,007
JBrowse link
G Tnfsf11 tumor necrosis factor (ligand) superfamily, member 11 decreases activity EXP quercetin 3-O-glucuronide results in decreased activity of TNFSF11 protein CTD PMID:19495926 NCBI chr14:78,277,446...78,308,043
Ensembl chr14:78,277,445...78,308,043
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 3:116,110,020...116,129,688
Ensembl chr 3:116,109,949...116,129,688
JBrowse link

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  CHEBI ontology 21569
    role 21548
      chemical role 20822
        antioxidant 14421
          miquelianin 33
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  CHEBI ontology 21569
    subatomic particle 21555
      composite particle 21555
        hadron 21555
          baryon 21555
            nucleon 21555
              atomic nucleus 21555
                atom 21555
                  main group element atom 21461
                    p-block element atom 21461
                      carbon group element atom 21254
                        carbon atom 21151
                          organic molecular entity 21151
                            organic molecule 21045
                              organic cyclic compound 20601
                                organic heterocyclic compound 19451
                                  oxacycle 17573
                                    benzopyran 10457
                                      1-benzopyran 10179
                                        flavonoid 6497
                                          flavones 4233
                                            hydroxyflavone 4221
                                              flavonols 4133
                                                7-hydroxyflavonol 4084
                                                  quercetin 4033
                                                    quercetin O-glycoside 427
                                                      miquelianin 33
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