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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:skatole
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Accession:CHEBI:9171 term browser browse the term
Definition:A methylindole carrying a methyl substituent at position 3. It is produced during the anoxic metabolism of L-tryptophan in the mammalian digestive tract.
Synonyms:related_synonym: 3-Methylindole;   3-methyl-1H-indole;   3-methyl-4,5-benzopyrrole;   Formula=C9H9N;   InChI=1S/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3;   InChIKey=ZFRKQXVRDFCRJG-UHFFFAOYSA-N;   SMILES=Cc1c[nH]c2ccccc12;   Skatol;   beta-methylindole
 xref: Beilstein:111296;   CAS:83-34-1;   Gmelin:396961;   HMDB:HMDB0000466;   KEGG:C08313;   KNApSAcK:C00001430;   LINCS:LSM-3655
 xref_mesh: MESH:D012862
 xref: MetaCyc:SKATOLE;   PMID:16656260;   PMID:22950976;   PMID:24358366;   PMID:7487051;   Reaxys:111296;   Wikipedia:Skatole


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skatole term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Ahr aryl hydrocarbon receptor multiple interactions ISO [alpha-naphthoflavone binds to and results in decreased activity of AHR protein] inhibits the reaction [Skatole results in increased expression of CYP1A1 mRNA]; [alpha-naphthoflavone binds to and results in decreased activity of AHR protein] inhibits the reaction [Skatole results in increased expression of CYP2F1 mRNA] CTD PMID:20187624 NCBI chr 6:54,963,990...55,001,806
Ensembl chr 6:54,963,990...55,001,464
JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 multiple interactions
increases expression
increases metabolic processing
ISO 1-aminobenzotriazole inhibits the reaction [Skatole results in increased expression of CYP1A1 mRNA]; [alpha-naphthoflavone binds to and results in decreased activity of AHR protein] inhibits the reaction [Skatole results in increased expression of CYP1A1 mRNA]; [CYP1A1 protein results in increased metabolism of Skatole] which results in increased chemical synthesis of 3-methyleneindolenine; Cycloheximide promotes the reaction [Skatole results in increased expression of CYP1A1 mRNA]; CYP1A1 protein results in increased metabolism of and results in increased activity of Skatole; Dactinomycin inhibits the reaction [Skatole results in increased expression of CYP1A1 mRNA]; Skatole inhibits the reaction [Tetrachlorodibenzodioxin results in increased activity of CYP1A1 protein]
Skatole metabolite results in increased expression of CYP1A1 mRNA; Skatole results in increased expression of CYP1A1 mRNA; Skatole results in increased expression of CYP1A1 protein
CTD PMID:20187624, PMID:20795680, PMID:28571685, PMID:31201936 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 Skatole results in increased expression of CYP1A2 mRNA; Skatole results in increased expression of CYP1A2 protein CTD PMID:28571685, PMID:31201936 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 Skatole results in increased expression of CYP1B1 mRNA CTD PMID:28571685 NCBI chr 6:2,308,179...2,316,739
Ensembl chr 6:2,307,808...2,316,722
JBrowse link
G Cyp2e1 cytochrome P450, family 2, subfamily e, polypeptide 1 decreases expression ISO Skatole results in decreased expression of CYP2E1 mRNA CTD PMID:28571685 NCBI chr 1:213,511,892...213,522,195
Ensembl chr 1:213,511,874...213,535,542
JBrowse link
G Cyp2f4 cytochrome P450, family 2, subfamily f, polypeptide 4 increases expression
multiple interactions
increases metabolic processing
ISO Skatole metabolite results in increased expression of CYP2F1 mRNA
1-aminobenzotriazole inhibits the reaction [Skatole results in increased expression of CYP2F1 mRNA]; [alpha-naphthoflavone binds to and results in decreased activity of AHR protein] inhibits the reaction [Skatole results in increased expression of CYP2F1 mRNA]; [CYP2F1 protein results in increased metabolism of Skatole] which results in increased chemical synthesis of 3-methyleneindolenine; Cycloheximide inhibits the reaction [Skatole results in increased expression of CYP2F1 mRNA]; CYP2F1 protein results in increased metabolism of and results in increased activity of Skatole; Dactinomycin inhibits the reaction [Skatole results in increased expression of CYP2F1 mRNA]
CTD PMID:20187624, PMID:20795680 NCBI chr 1:83,933,974...83,947,804
Ensembl chr 1:83,933,942...83,947,821
JBrowse link
G Cyp4b1 cytochrome P450, family 4, subfamily b, polypeptide 1 multiple interactions
increases metabolic processing
ISO [CYP4B1 protein results in increased metabolism of Skatole] which results in increased chemical synthesis of 3-methyleneindolenine CTD PMID:20187624 NCBI chr 5:134,508,728...134,526,103
Ensembl chr 5:134,508,730...134,526,089
JBrowse link
G Nr1i2 nuclear receptor subfamily 1, group I, member 2 decreases expression ISO Skatole results in decreased expression of NR1I2 mRNA CTD PMID:28571685 NCBI chr11:65,022,100...65,058,546
Ensembl chr11:65,022,100...65,058,545
JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 increases cleavage ISO Skatole results in increased cleavage of PARP1 protein CTD PMID:19700606 NCBI chr13:98,857,255...98,889,444
Ensembl chr13:98,857,177...98,889,716
JBrowse link
G Tp53 tumor protein p53 multiple interactions ISO Skatole results in increased phosphorylation of and affects the localization of TP53 protein CTD PMID:19700606 NCBI chr10:56,186,299...56,198,449
Ensembl chr10:56,187,020...56,198,449
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19792
    role 19738
      biological role 19737
        biochemical role 19241
          metabolite 19218
            eukaryotic metabolite 18842
              animal metabolite 18569
                mammalian metabolite 18558
                  skatole 10
Path 2
Term Annotations click to browse term
  CHEBI ontology 19792
    subatomic particle 19788
      composite particle 19788
        hadron 19788
          baryon 19788
            nucleon 19788
              atomic nucleus 19788
                atom 19788
                  main group element atom 19675
                    p-block element atom 19675
                      carbon group element atom 19571
                        carbon atom 19560
                          organic molecular entity 19560
                            organic molecule 19483
                              organic cyclic compound 19252
                                organic heterocyclic compound 18422
                                  organic heteropolycyclic compound 17835
                                    organic heterobicyclic compound 16764
                                      benzopyrrole 9342
                                        indoles 9196
                                          methylindole 1273
                                            skatole 10
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.