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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


show annotations for term's descendants           Sort by:
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 chr15:95,541,186...95,774,898
Ensembl chr15:95,542,315...95,774,283 		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 4:87,676,241...87,802,757
Ensembl chr 4:87,745,319...87,802,409 		JBrowse link
G Ace angiotensin I converting enzyme increases expression EXP Indican results in increased expression of ACE mRNA CTD PMID:25056788 NCBI chr10:90,910,316...90,930,437
Ensembl chr10:90,910,316...90,931,131 		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 6:52,234,089...52,271,568
Ensembl chr 6:52,234,089...52,271,568 		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 2:182,997,731...183,056,584
Ensembl chr 2:182,997,736...183,056,580 		JBrowse link
G Casp3 caspase 3 increases cleavage EXP Indican results in increased cleavage of CASP3 protein CTD PMID:25056788 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		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 chr10:67,005,424...67,007,222
Ensembl chr10:67,005,424...67,007,226 		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 9:84,389,031...84,391,629
Ensembl chr 9:84,388,904...84,391,629 		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 chr20:7,149,177...7,159,727
Ensembl chr20:7,149,217...7,159,585 		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 8:58,096,021...58,102,130
Ensembl chr 8:58,096,077...58,102,125 		JBrowse link
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 increases expression ISO Indican results in increased expression of CYP1A2 mRNA CTD PMID:20000589 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 expression ISO Indican results in increased expression of CYP1B1 mRNA CTD PMID:20000589 NCBI chr 6:15,342,312...15,350,886
Ensembl chr 6:15,342,344...15,350,917 		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 5:19,376,979...19,386,676
Ensembl chr 5:19,376,974...19,386,688 		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 6:97,672,829...97,697,499
Ensembl chr 6:97,672,766...97,706,225 		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 6:7,790,236...7,871,246
Ensembl chr 6:7,790,647...7,871,228 		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 chr12:19,204,258...19,207,948
Ensembl chr12:19,204,508...19,207,946 		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 7:89,731,626...89,764,761
Ensembl chr 7:89,730,232...89,765,436 		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 chr20:35,756,007...35,768,481
Ensembl chr20:35,755,991...35,768,582 		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 6:92,624,059...92,669,262
Ensembl chr 6:92,624,390...92,669,261 		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 3:18,055,507...18,059,969
Ensembl chr 3:18,055,405...18,059,891 		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 8:19,553,063...19,565,438
Ensembl chr 8:19,553,645...19,565,438 		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 chr12:490,402...531,417
Ensembl chr12:490,399...530,080 		JBrowse link
G Lepr leptin receptor affects abundance ISO LEPR affects the abundance of Indican CTD PMID:20567778 NCBI chr 5:116,294,409...116,477,904
Ensembl chr 5:116,289,823...116,475,908 		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 chr19:49,665,795...49,673,655
Ensembl chr19:49,665,791...49,677,690 		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 chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616 		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 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		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 chr16:8,638,897...8,721,960
Ensembl chr16:8,638,924...8,721,981 		JBrowse link
G Mapk9 mitogen-activated protein kinase 9 increases phosphorylation EXP Indican results in increased phosphorylation of MAPK9 protein CTD PMID:32045570 NCBI chr10:34,169,661...34,211,138
Ensembl chr10:34,169,675...34,210,178 		JBrowse link
G Myh2 myosin heavy chain 2 decreases expression ISO Indican results in decreased expression of MYH2 mRNA CTD PMID:29380555 NCBI chr10:51,856,738...51,883,236
Ensembl chr10:51,856,738...51,883,236 		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 chr10:51,770,177...51,793,994
Ensembl chr10:51,770,177...51,793,992 		JBrowse link
G Myh7 myosin heavy chain 7 increases expression EXP Indican results in increased expression of MYH7 mRNA CTD PMID:25703824 NCBI chr15:28,446,550...28,469,888
Ensembl chr15:28,446,550...28,468,217 		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 3:145,281,943...145,288,333
Ensembl chr 3:145,281,937...145,288,333 		JBrowse link
G Myod1 myogenic differentiation 1 decreases expression ISO Indican results in decreased expression of MYOD1 protein CTD PMID:29380555 NCBI chr 1:96,884,864...96,887,574
Ensembl chr 1:96,884,948...96,887,554 		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 chr13:45,745,455...45,748,044
Ensembl chr13:45,745,436...45,748,039 		JBrowse link
G Nox4 NADPH oxidase 4 increases expression ISO Indican results in increased expression of NOX4 mRNA CTD PMID:23325087 NCBI chr 1:140,900,886...141,078,844
Ensembl chr 1:140,901,097...141,077,406 		JBrowse link
G Nppa natriuretic peptide A increases expression EXP Indican results in increased expression of NPPA mRNA CTD PMID:25703824 NCBI chr 5:158,429,042...158,430,351
Ensembl chr 5:158,429,042...158,430,351 		JBrowse link
G Nppb natriuretic peptide B increases expression EXP Indican results in increased expression of NPPB mRNA CTD PMID:25703824 NCBI chr 5:158,416,813...158,418,175
Ensembl chr 5:158,416,866...158,418,168 		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 3:119,186,073...119,201,513
Ensembl chr 3:119,177,485...119,203,937 		JBrowse link
G Ren renin increases expression EXP Indican results in increased expression of REN mRNA CTD PMID:25056788 NCBI chr13:44,796,260...44,807,491
Ensembl chr13:44,796,091...44,807,489 		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:1,619,030...1,634,456
Ensembl chr  X:1,619,032...1,634,450 		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 2:182,009,707...182,034,910
Ensembl chr 2:182,009,286...182,034,907 		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 6:100,613,045...100,626,670
Ensembl chr 6:100,613,045...100,626,670 		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 4:174,551,463...174,619,988
Ensembl chr 4:174,551,480...174,619,981 		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 1:128,115,184...128,387,887
Ensembl chr 1:128,106,228...128,387,925 		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 3:146,091,969...146,139,492
Ensembl chr 3:146,091,841...146,139,476 		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 chr10:85,811,206...85,863,057
Ensembl chr10:85,811,218...85,863,057 		JBrowse link
G Ucp2 uncoupling protein 2 multiple interactions
decreases expression
decreases response to substance		 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 1:154,839,242...154,845,612
Ensembl chr 1:154,839,209...154,845,611 		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 9:88,801,344...88,808,465
Ensembl chr 9:88,713,184...88,808,465 		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 9:88,747,229...88,808,465
Ensembl chr 9:88,713,184...88,808,465 		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 2:204,038,120...204,057,852
Ensembl chr 2:204,038,114...204,057,958 		JBrowse link
G Xbp1 X-box binding protein 1 increases splicing ISO Indican results in increased splicing of XBP1 mRNA CTD PMID:29380555 NCBI chr14:80,390,629...80,395,713
Ensembl chr14:80,390,643...80,395,693 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19757
    role 19730
      chemical role 19370
        catalyst 8212
          sulfuric acid 8160
            sulfuric acid derivative 8160
              organic sulfate 2138
                aryl sulfate 54
                  indoxyl sulfate 51
Path 2
Term Annotations click to browse term
  CHEBI ontology 19757
    subatomic particle 19755
      composite particle 19755
        hadron 19755
          baryon 19755
            nucleon 19755
              atomic nucleus 19755
                atom 19755
                  main group element atom 19703
                    p-block element atom 19703
                      carbon group element atom 19649
                        carbon atom 19645
                          organic molecular entity 19645
                            organic molecule 19604
                              organic cyclic compound 19407
                                organic heterocyclic compound 18772
                                  organic heteropolycyclic compound 18256
                                    organic heterobicyclic compound 17218
                                      benzopyrrole 9604
                                        indoles 9277
                                          hydroxyindoles 169
                                            indoxyl 51
                                              indoxyl sulfate 51
paths to the root