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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:indoxyl sulfate
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Accession:CHEBI:43355 term browser browse the term
Definition:An aryl sulfate that is indoxyl in which the hydroxyl hydrogen is substituted by a sulfo group.
Synonyms:related_synonym: 1H-Indol-3-yl hydrogen sulfate;   3-Indoxyl sulfate;   3-Indoxylsulfuric acid;   3-indolyl hydrogen sulfate;   3-indolyl sulfate;   Formula=C8H7NO4S;   InChI=1S/C8H7NO4S/c10-14(11,12)13-8-5-9-7-4-2-1-3-6(7)8/h1-5,9H,(H,10,11,12);   InChIKey=BXFFHSIDQOFMLE-UHFFFAOYSA-N;   Indican;   Indol-3-yl sulfate;   Indoxyl sulfic acid;   Indoxylsulfuric acid;   SMILES=OS(=O)(=O)Oc1c[nH]c2ccccc12;   indol-3-yl hydrogen sulfate;   indol-3-yl sulphate;   indoxyl sulphate;   indoxyl-3-sulphate
 xref: CAS:487-94-5;   HMDB:HMDB0000682
 xref_mesh: MESH:D007200
 xref: PDBeChem:IOS;   PMID:17190852;   PMID:22056374;   PMID:22200421;   PMID:22200422;   PMID:22200425;   PMID:22200426;   PMID:22213462;   PMID:22231736;   PMID:22237753;   PMID:22318422;   PMID:22326498;   PMID:22389425;   PMID:22447217;   PMID:22483453;   PMID:22490877;   PMID:22513409;   Reaxys:188887
 cyclic_relationship: is_conjugate_acid_of CHEBI:144643

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indoxyl sulfate term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcc4 ATP binding cassette subfamily C member 4 multiple interactions ISO Indican inhibits the reaction [ABCC4 protein results in increased export of Methotrexate] CTD PMID:21483698 NCBI chr15:103,695,415...103,927,980
Ensembl chr15:103,696,557...103,927,592 		JBrowse link
G Abcg2 ATP binding cassette subfamily G member 2 multiple interactions ISO Indican inhibits the reaction [ABCG2 protein results in increased export of estrone sulfate] CTD PMID:21483698 NCBI chr 4:88,765,441...88,890,268
Ensembl chr 4:88,832,178...88,890,621 		JBrowse link
G Ace angiotensin I converting enzyme increases expression EXP Indican results in increased expression of ACE mRNA CTD PMID:25056788 NCBI chr10:94,170,766...94,213,831
Ensembl chr10:94,170,766...94,187,822 		JBrowse link
G Ahr aryl hydrocarbon receptor multiple interactions
increases expression
increases activity		 ISO Flavones inhibits the reaction [Indican results in increased activity of AHR protein]; Indican binds to and results in increased activity of AHR protein; N-(2-(3H-indol-3-yl)ethyl)-9-isopropyl-2-(5-methyl-3-pyridyl)purin-6-amine inhibits the reaction [Indican results in increased expression of AHR mRNA]
Indican promotes the reaction [[AHR protein binds to ARNT protein] which binds to CCL20 promoter]		 CTD PMID:20000589, PMID:21493753, PMID:23639249, PMID:26259605 NCBI chr 6:54,963,990...55,001,806
Ensembl chr 6:54,963,990...55,001,464 		JBrowse link
G Arnt aryl hydrocarbon receptor nuclear translocator multiple interactions ISO Indican promotes the reaction [[AHR protein binds to ARNT protein] which binds to CCL20 promoter] CTD PMID:26259605 NCBI chr 2:196,594,178...196,651,486
Ensembl chr 2:196,594,303...196,651,179 		JBrowse link
G Casp3 caspase 3 increases cleavage EXP Indican results in increased cleavage of CASP3 protein CTD PMID:25056788 NCBI chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204 		JBrowse link
G Ccl2 C-C motif chemokine ligand 2 increases expression ISO Indican results in increased expression of CCL2 mRNA; Indican results in increased expression of CCL2 protein CTD PMID:22056374 NCBI chr10:69,412,065...69,413,863
Ensembl chr10:69,412,017...69,413,870 		JBrowse link
G Ccl20 C-C motif chemokine ligand 20 multiple interactions ISO Indican promotes the reaction [[AHR protein binds to ARNT protein] which binds to CCL20 promoter] CTD PMID:26259605 NCBI chr 9:88,918,359...88,921,017
Ensembl chr 9:88,918,433...88,921,001 		JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A increases expression
multiple interactions		 ISO Indican results in increased expression of CDKN1A protein
Melatonin inhibits the reaction [Indican results in increased expression of CDKN1A protein]; Melatonin promotes the reaction [Pioglitazone inhibits the reaction [Indican results in increased expression of CDKN1A protein]]; Pioglitazone inhibits the reaction [Indican results in increased expression of CDKN1A protein]; Pioglitazone promotes the reaction [Melatonin inhibits the reaction [Indican results in increased expression of CDKN1A protein]]; PRNP protein promotes the reaction [Melatonin promotes the reaction [Pioglitazone inhibits the reaction [Indican results in increased expression of CDKN1A protein]]]; PRNP protein promotes the reaction [Pioglitazone promotes the reaction [Melatonin inhibits the reaction [Indican results in increased expression of CDKN1A protein]]]		 CTD PMID:29734669 NCBI chr20:6,348,422...6,358,864
Ensembl chr20:6,351,458...6,358,864 		JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 increases expression ISO Indican results in increased expression of CYP1A1 mRNA CTD PMID:20000589, PMID:23639249 NCBI chr 8:62,472,087...62,478,122
Ensembl chr 8:62,472,095...62,478,147 		JBrowse link
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 increases expression ISO Indican results in increased expression of CYP1A2 mRNA CTD PMID:20000589 NCBI chr 8:62,451,360...62,458,244
Ensembl chr 8:62,451,329...62,458,301 		JBrowse link
G Cyp1b1 cytochrome P450, family 1, subfamily b, polypeptide 1 increases expression ISO Indican results in increased expression of CYP1B1 mRNA CTD PMID:20000589 NCBI chr 6:2,308,179...2,316,739
Ensembl chr 6:2,307,808...2,316,722 		JBrowse link
G Cyp7a1 cytochrome P450 family 7 subfamily A member 1 decreases expression ISO Indican results in decreased expression of CYP7A1 mRNA CTD PMID:30639138 NCBI chr 5:19,358,734...19,368,431
Ensembl chr 5:19,358,734...19,368,431 		JBrowse link
G Eif2s1 eukaryotic translation initiation factor 2 subunit alpha increases phosphorylation
multiple interactions		 ISO Indican results in increased phosphorylation of EIF2S1 protein
Acetylcysteine inhibits the reaction [Indican results in increased phosphorylation of EIF2S1 protein]		 CTD PMID:29380555 NCBI chr 6:102,048,372...102,073,041
Ensembl chr 6:102,048,372...102,073,041 		JBrowse link
G Epas1 endothelial PAS domain protein 1 multiple interactions ISO Indican inhibits the reaction [cobaltous chloride affects the localization of EPAS1 protein] CTD PMID:21863063 NCBI chr 6:10,306,508...10,385,239
Ensembl chr 6:10,306,405...10,387,265 		JBrowse link
G Epo erythropoietin multiple interactions ISO Indican inhibits the reaction [cobaltous chloride results in increased expression of EPO mRNA]; Indican inhibits the reaction [Oxygen deficiency results in increased expression of EPO mRNA] CTD PMID:21863063 NCBI chr12:22,274,828...22,278,268
Ensembl chr12:22,274,828...22,278,266 		JBrowse link
G Fbxo32 F-box protein 32 multiple interactions
increases expression		 ISO Acetylcysteine inhibits the reaction [Indican results in increased expression of FBXO32 protein]; pyrazolanthrone inhibits the reaction [Indican results in increased expression of FBXO32 protein]
Indican results in increased expression of FBXO32 mRNA; Indican results in increased expression of FBXO32 protein		 CTD PMID:29380555, PMID:30849338 NCBI chr 7:98,065,664...98,098,071
Ensembl chr 7:98,063,735...98,098,268 		JBrowse link
G Gja1 gap junction protein, alpha 1 multiple interactions
decreases expression		 EXP Indican results in decreased expression of and affects the localization of GJA1 protein; pyrazolanthrone inhibits the reaction [Indican results in decreased expression of and affects the localization of GJA1 protein]; pyrazolanthrone inhibits the reaction [Indican results in decreased expression of GJA1 mRNA]
Indican results in decreased expression of GJA1 mRNA; Indican results in decreased expression of GJA1 protein modified form		 CTD PMID:32045570 NCBI chr20:37,876,650...37,889,097
Ensembl chr20:37,876,650...37,889,089 		JBrowse link
G Hif1a hypoxia inducible factor 1 subunit alpha multiple interactions ISO Indican inhibits the reaction [cobaltous chloride affects the localization of HIF1A protein] CTD PMID:21863063 NCBI chr 6:96,810,868...96,856,303
Ensembl chr 6:96,810,907...96,856,052 		JBrowse link
G Hspa5 heat shock protein family A (Hsp70) member 5 increases expression ISO Indican results in increased expression of HSPA5 mRNA CTD PMID:29380555 NCBI chr 3:13,838,304...13,842,763
Ensembl chr 3:13,838,304...13,842,762 		JBrowse link
G Icam1 intercellular adhesion molecule 1 increases expression ISO Indican results in increased expression of ICAM1 mRNA; Indican results in increased expression of ICAM1 protein CTD PMID:22056374 NCBI chr 8:22,035,287...22,047,049
Ensembl chr 8:22,035,256...22,047,059 		JBrowse link
G Kl Klotho multiple interactions
decreases expression		 ISO
EXP		 Acetylcysteine inhibits the reaction [Indican results in decreased expression of KL mRNA]; Acetylcysteine inhibits the reaction [Indican results in decreased expression of KL protein]; isohelenin inhibits the reaction [Indican results in decreased expression of KL mRNA]; isohelenin inhibits the reaction [Indican results in decreased expression of KL protein]; pyrrolidine dithiocarbamic acid inhibits the reaction [Indican results in decreased expression of KL mRNA]; pyrrolidine dithiocarbamic acid inhibits the reaction [Indican results in decreased expression of KL protein]
Indican results in decreased expression of KL mRNA; Indican results in decreased expression of KL protein		 CTD PMID:21389697 NCBI chr12:942,974...987,206
Ensembl chr12:943,006...987,551 		JBrowse link
G Lepr leptin receptor affects abundance ISO LEPR affects the abundance of Indican CTD PMID:20567778 NCBI chr 5:120,503,475...120,682,281
Ensembl chr 5:120,564,645...120,682,221 		JBrowse link
G Map1lc3b microtubule-associated protein 1 light chain 3 beta increases expression
multiple interactions		 ISO Indican results in increased expression of MAP1LC3B protein
Acetylcysteine inhibits the reaction [Indican results in increased expression of MAP1LC3B protein]		 CTD PMID:30849338 NCBI chr19:53,635,449...53,643,970
Ensembl chr19:53,629,779...53,646,058 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions
increases phosphorylation		 ISO Acetylcysteine inhibits the reaction [Indican results in increased phosphorylation of MAPK1 protein] CTD PMID:30849338 NCBI chr11:88,203,863...88,273,301
Ensembl chr11:88,211,599...88,273,254 		JBrowse link
G Mapk3 mitogen activated protein kinase 3 increases phosphorylation
multiple interactions		 ISO Indican results in increased phosphorylation of MAPK3 protein
Acetylcysteine inhibits the reaction [Indican results in increased phosphorylation of MAPK3 protein]		 CTD PMID:30849338 NCBI chr 1:198,192,773...198,198,975
Ensembl chr 1:198,192,773...198,198,975 		JBrowse link
G Mapk8 mitogen-activated protein kinase 8 multiple interactions
increases phosphorylation		 ISO
EXP		 Indican results in increased expression of and results in increased phosphorylation of MAPK8 protein
Indican results in increased phosphorylation of MAPK8 protein		 CTD PMID:30849338, PMID:32045570 NCBI chr16:9,620,854...9,709,342
Ensembl chr16:9,625,177...9,709,347 		JBrowse link
G Mapk9 mitogen-activated protein kinase 9 increases phosphorylation EXP Indican results in increased phosphorylation of MAPK9 protein CTD PMID:32045570 NCBI chr10:35,333,859...35,374,364
Ensembl chr10:35,333,859...35,374,355 		JBrowse link
G Myh2 myosin heavy chain 2 decreases expression ISO Indican results in decreased expression of MYH2 mRNA CTD PMID:29380555 NCBI chr10:53,711,895...53,738,164
Ensembl chr10:53,713,938...53,848,347 		JBrowse link
G Myh3 myosin heavy chain 3 multiple interactions
decreases expression		 ISO Acetylcysteine inhibits the reaction [Indican results in decreased expression of MYH3 protein] CTD PMID:29380555 NCBI chr10:53,621,375...53,645,194
Ensembl chr10:53,621,375...53,645,194 		JBrowse link
G Myh7 myosin heavy chain 7 increases expression EXP Indican results in increased expression of MYH7 mRNA CTD PMID:25703824 NCBI chr15:33,605,769...33,657,761
Ensembl chr15:33,634,422...33,656,089 		JBrowse link
G Myl9 myosin light chain 9 multiple interactions ISO Indican results in decreased expression of and results in increased phosphorylation of MYL9 protein CTD PMID:30849338 NCBI chr 3:152,857,573...152,863,961
Ensembl chr 3:152,857,592...152,863,960 		JBrowse link
G Myod1 myogenic differentiation 1 decreases expression ISO Indican results in decreased expression of MYOD1 protein CTD PMID:29380555 NCBI chr 1:102,396,538...102,399,248
Ensembl chr 1:102,396,538...102,399,248 		JBrowse link
G Myog myogenin multiple interactions
decreases expression		 ISO Acetylcysteine inhibits the reaction [Indican results in decreased expression of MYOG protein]
Indican results in decreased expression of MYOG mRNA; Indican results in decreased expression of MYOG protein		 CTD PMID:29380555 NCBI chr13:51,126,459...51,129,048
Ensembl chr13:51,126,459...51,129,048 		JBrowse link
G Nox4 NADPH oxidase 4 increases expression ISO Indican results in increased expression of NOX4 mRNA CTD PMID:23325087 NCBI chr 1:150,796,359...150,976,186
Ensembl chr 1:150,797,084...150,976,194 		JBrowse link
G Nppa natriuretic peptide A increases expression EXP Indican results in increased expression of NPPA mRNA CTD PMID:25703824 NCBI chr 5:164,808,407...164,809,716
Ensembl chr 5:164,808,323...164,809,705 		JBrowse link
G Nppb natriuretic peptide B increases expression EXP Indican results in increased expression of NPPB mRNA CTD PMID:25703824 NCBI chr 5:164,796,176...164,797,538
Ensembl chr 5:164,796,185...164,797,531 		JBrowse link
G Prnp prion protein multiple interactions ISO PRNP protein promotes the reaction [Melatonin promotes the reaction [Pioglitazone inhibits the reaction [Indican results in decreased expression of RGN protein]]]; PRNP protein promotes the reaction [Melatonin promotes the reaction [Pioglitazone inhibits the reaction [Indican results in increased expression of CDKN1A protein]]]; PRNP protein promotes the reaction [Pioglitazone promotes the reaction [Melatonin inhibits the reaction [Indican results in decreased expression of RGN protein]]]; PRNP protein promotes the reaction [Pioglitazone promotes the reaction [Melatonin inhibits the reaction [Indican results in increased expression of CDKN1A protein]]] CTD PMID:29734669 NCBI chr 3:124,515,917...124,531,320
Ensembl chr 3:124,515,978...124,531,316 		JBrowse link
G Ren renin increases expression EXP Indican results in increased expression of REN mRNA CTD PMID:25056788 NCBI chr13:50,502,724...50,513,953
Ensembl chr13:50,502,724...50,514,151 		JBrowse link
G Rgn regucalcin decreases expression
multiple interactions		 ISO Indican results in decreased expression of RGN protein
Melatonin inhibits the reaction [Indican results in decreased expression of RGN protein]; Melatonin promotes the reaction [Pioglitazone inhibits the reaction [Indican results in decreased expression of RGN protein]]; Pioglitazone inhibits the reaction [Indican results in decreased expression of RGN protein]; Pioglitazone promotes the reaction [Melatonin inhibits the reaction [Indican results in decreased expression of RGN protein]]; PRNP protein promotes the reaction [Melatonin promotes the reaction [Pioglitazone inhibits the reaction [Indican results in decreased expression of RGN protein]]]; PRNP protein promotes the reaction [Pioglitazone promotes the reaction [Melatonin inhibits the reaction [Indican results in decreased expression of RGN protein]]]		 CTD PMID:29734669 NCBI chr  X:1,833,484...1,848,904
Ensembl chr  X:1,833,492...1,848,904 		JBrowse link
G Rorc RAR-related orphan receptor C increases expression ISO Indican results in increased expression of RORC mRNA CTD PMID:23639249 NCBI chr 2:195,612,471...195,636,797
Ensembl chr 2:195,617,021...195,637,630 		JBrowse link
G Slc10a1 solute carrier family 10 member 1 decreases expression ISO Indican results in decreased expression of SLC10A1 mRNA CTD PMID:30639138 NCBI chr 6:104,617,730...104,631,355
Ensembl chr 6:104,617,730...104,631,355 		JBrowse link
G Slco1b2 solute carrier organic anion transporter family member 1B2 decreases expression ISO Indican results in decreased expression of SLCO1B3 mRNA CTD PMID:30639138 NCBI chr 4:175,814,118...175,881,775
Ensembl chr 4:175,814,118...175,881,768 		JBrowse link
G Slco3a1 solute carrier organic anion transporter family, member 3a1 multiple interactions ISO Indican promotes the reaction [SLCO3A1 protein results in increased uptake of simvastatin acid] CTD PMID:28887287 NCBI chr 1:135,790,854...136,073,640
Ensembl chr 1:135,790,810...136,073,540 		JBrowse link
G Src SRC proto-oncogene, non-receptor tyrosine kinase multiple interactions
increases phosphorylation		 ISO [AG 1879 results in decreased activity of SRC protein] inhibits the reaction [Indican results in increased phosphorylation of SRC protein]; [AG 1879 results in decreased activity of SRC protein] inhibits the reaction [Indican results in increased phosphorylation of STAT3 protein] CTD PMID:23639249 NCBI chr 3:153,547,807...153,595,643
Ensembl chr 3:153,580,861...153,595,642 		JBrowse link
G Stat3 signal transducer and activator of transcription 3 multiple interactions ISO [AG 1879 results in decreased activity of SRC protein] inhibits the reaction [Indican results in increased phosphorylation of STAT3 protein]; Indican results in increased phosphorylation of and results in increased activity of STAT3 protein CTD PMID:23639249 NCBI chr10:88,790,401...88,842,263
Ensembl chr10:88,790,408...88,842,233 		JBrowse link
G Ucp2 uncoupling protein 2 multiple interactions
decreases response to substance
decreases expression		 EXP AICA ribonucleotide inhibits the reaction [Indican results in decreased expression of UCP2 mRNA]
UCP2 protein results in decreased susceptibility to Indican		 CTD PMID:25703824 NCBI chr 1:165,506,375...165,512,744
Ensembl chr 1:165,506,361...165,512,744 		JBrowse link
G Ugt1a1 UDP glucuronosyltransferase family 1 member A1 increases expression ISO Indican results in increased expression of UGT1A1 mRNA CTD PMID:20000589 NCBI chr 9:95,295,701...95,302,822
Ensembl chr 9:95,161,157...95,302,822 		JBrowse link
G Ugt1a6 UDP glucuronosyltransferase family 1 member A6 increases expression ISO Indican results in increased expression of UGT1A6 mRNA CTD PMID:20000589 NCBI chr 9:95,241,609...95,302,822
Ensembl chr 9:95,161,157...95,302,822 		JBrowse link
G Vcam1 vascular cell adhesion molecule 1 increases expression ISO Indican results in increased expression of VCAM1 mRNA; Indican results in increased expression of VCAM1 protein CTD PMID:22056374 NCBI chr 2:219,071,193...219,090,931
Ensembl chr 2:219,071,193...219,097,619 		JBrowse link
G Xbp1 X-box binding protein 1 increases splicing ISO Indican results in increased splicing of XBP1 mRNA CTD PMID:29380555 NCBI chr14:85,753,736...85,758,820
Ensembl chr14:85,753,760...85,758,145 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19787
    role 19734
      chemical role 19250
        catalyst 8050
          sulfuric acid 8011
            sulfuric acid derivative 8011
              organic sulfate 1933
                aryl sulfate 54
                  indoxyl sulfate 51
Path 2
Term Annotations click to browse term
  CHEBI ontology 19787
    subatomic particle 19784
      composite particle 19784
        hadron 19784
          baryon 19784
            nucleon 19784
              atomic nucleus 19784
                atom 19784
                  main group element atom 19672
                    p-block element atom 19672
                      carbon group element atom 19574
                        carbon atom 19563
                          organic molecular entity 19563
                            organic molecule 19488
                              organic cyclic compound 19285
                                organic heterocyclic compound 18410
                                  organic heteropolycyclic compound 17824
                                    organic heterobicyclic compound 16744
                                      benzopyrrole 9340
                                        indoles 9194
                                          hydroxyindoles 159
                                            indoxyl 51
                                              indoxyl sulfate 51
paths to the root

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