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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:oleandolide
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Accession:CHEBI:29658 term browser browse the term
Definition:A 14-membererd macrolide containing ten stereocentres carrying one epoxymethano, three hydroxy and five methyl substituents. It is the aglycone of the antibiotic oleandomycin.
Synonyms:exact_synonym: (3R,5R,6S,7R,8R,11R,12S,13R,14S,15S)-6,12,14-trihydroxy-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione
 related_synonym: Formula=C20H34O7;   InChI=1S/C20H34O7/c1-9-7-20(8-26-20)18(24)12(4)16(22)10(2)14(6)27-19(25)13(5)17(23)11(3)15(9)21/h9-17,21-23H,7-8H2,1-6H3/t9-,10-,11+,12+,13+,14+,15-,16-,17-,20+/m0/s1;   InChIKey=PFDLUBNRHMFBGI-HRVFELILSA-N;   Oleandomycin aglycone;   Oleandonolide;   SMILES=C[C@H]1C[C@@]2(CO2)C(=O)[C@H](C)[C@@H](O)[C@@H](C)[C@@H](C)OC(=O)[C@H](C)[C@@H](O)[C@H](C)[C@H]1O
 xref: CAS:68540-16-9;   LIPID_MAPS_instance:LMPK04000031;   Reaxys:3566509


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troleandomycin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb1a ATP binding cassette subfamily B member 1A multiple interactions ISO Troleandomycin inhibits the reaction [ABCB1 protein results in increased secretion of fluorexon]; Troleandomycin inhibits the reaction [ABCB1 protein results in increased secretion of Vinblastine]
Troleandomycin inhibits the reaction [ABCB1A protein results in increased secretion of fluorexon]
CTD PMID:12235267 NCBI chr 4:22,339,829...22,517,642
Ensembl chr 4:22,133,521...22,425,515
JBrowse link
G Cyp3a23-3a1 cytochrome P450, family 3, subfamily a, polypeptide 23-polypeptide 1 increases expression EXP Troleandomycin results in increased expression of CYP3A23-3A1 mRNA CTD PMID:12971794 NCBI chr12:11,053,888...11,082,742
Ensembl chr12:11,655,402...11,733,136
JBrowse link
G Cyp3a62 cytochrome P450, family 3, subfamily a, polypeptide 62 decreases activity
increases activity
increases expression
multiple interactions
ISO Troleandomycin results in decreased activity of CYP3A4 protein
Troleandomycin results in increased activity of CYP3A4 protein
Troleandomycin results in increased expression of CYP3A4 mRNA
[Troleandomycin results in decreased activity of CYP3A4 protein] which results in decreased chemical synthesis of N-desmethyltamoxifen; [Troleandomycin results in decreased activity of CYP3A4 protein] which results in decreased metabolism of Tamoxifen; Troleandomycin inhibits the reaction [CYP3A4 protein results in decreased methylation of adinazolam]; Troleandomycin inhibits the reaction [CYP3A4 protein results in increased chemical synthesis of 1-hydroxymethylmidazolam]; Troleandomycin inhibits the reaction [CYP3A4 protein results in increased chemical synthesis of 4-hydroxymidazolam]; Troleandomycin inhibits the reaction [CYP3A4 protein results in increased chemical synthesis of 6 beta-hydroxytestosterone]; Troleandomycin inhibits the reaction [CYP3A4 protein results in increased hydroxylation of Cholecalciferol]; Troleandomycin inhibits the reaction [CYP3A4 protein results in increased hydroxylation of Midazolam]; Troleandomycin inhibits the reaction [CYP3A4 protein results in increased hydroxylation of Testosterone]; Troleandomycin inhibits the reaction [CYP3A4 protein results in increased metabolism of 4,5-dihydropyrazole-1,5-dicarboxylic acid 1-((4-chlorophenyl)-amide) 5-(2-oxo-2H-(1,3')bipyridinyl-6'-yl)-amide]; Troleandomycin inhibits the reaction [CYP3A4 protein results in increased metabolism of Fluoxetine]; Troleandomycin inhibits the reaction [CYP3A4 protein results in increased metabolism of laquinimod]; Troleandomycin inhibits the reaction [CYP3A4 protein results in increased metabolism of Midazolam]; Troleandomycin inhibits the reaction [CYP3A4 protein results in increased metabolism of triflumuron]; Troleandomycin inhibits the reaction [CYP3A4 protein results in increased oxidation of Methylenebis(chloroaniline)]; Troleandomycin inhibits the reaction [CYP3A4 protein results in increased oxidation of Nifedipine]; Troleandomycin promotes the reaction [CYP3A4 protein results in increased oxidation of 7-benzyloxy-4-trifluoromethylcoumarin]; Troleandomycin results in increased expression of and results in increased activity of CYP3A4 protein
CTD PMID:1740010 PMID:2271712 PMID:9512926 PMID:9600717 PMID:11409940 PMID:11752104 PMID:12467917 PMID:12695342 PMID:14652237 PMID:15005856 PMID:15557344 PMID:15764719 PMID:15860655 PMID:16049126 PMID:16207822 PMID:16416302 PMID:18505790 PMID:19299527 PMID:19697924 PMID:20863320 PMID:31082524 NCBI chr12:18,679,809...18,709,397
Ensembl chr12:18,678,594...18,709,397
JBrowse link
G Cyp3a9 cytochrome P450, family 3, subfamily a, polypeptide 9 multiple interactions
decreases activity
ISO Troleandomycin inhibits the reaction [CYP3A5 protein affects the metabolism of Alfentanil]
Troleandomycin results in decreased activity of CYP3A5 protein
CTD PMID:15557344 PMID:15731592 NCBI chr12:19,074,288...19,114,491
Ensembl chr12:19,074,583...19,114,399
JBrowse link
G Fn1 fibronectin 1 increases expression EXP Troleandomycin results in increased expression of FN1 mRNA CTD PMID:12971794 NCBI chr 9:78,900,111...78,969,018
Ensembl chr 9:78,900,103...78,969,078
JBrowse link
G Gsta2 glutathione S-transferase alpha 2 increases expression EXP Troleandomycin results in increased expression of GSTA2 mRNA CTD PMID:12971794 NCBI chr 8:85,640,081...85,645,621 JBrowse link
G Madcam1 mucosal vascular addressin cell adhesion molecule 1 multiple interactions ISO Troleandomycin inhibits the reaction [TNF protein results in increased expression of MADCAM1 protein] CTD PMID:12388057 NCBI chr 7:12,918,352...12,922,509
Ensembl chr 7:12,918,710...12,922,112
JBrowse link
G Nr1i2 nuclear receptor subfamily 1, group I, member 2 multiple interactions ISO Troleandomycin binds to and results in increased activity of NR1I2 protein CTD PMID:15039302 NCBI chr11:65,022,100...65,058,546
Ensembl chr11:65,022,100...65,058,545
JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO Troleandomycin inhibits the reaction [TNF protein results in increased expression of MADCAM1 protein] CTD PMID:12388057 NCBI chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19773
    chemical entity 19773
      molecular entity 19771
        main group molecular entity 19665
          gas molecular entity 17756
            oxirane 9523
              epoxide 9522
                spiro-epoxide 24
                  oleandolide 9
                    3-O-(alpha-L-oleandrosyl)oleandolide 0
                    3-O-(alpha-L-olivosyl)oleandolide 0
                    oleandomycin + 9
Path 2
Term Annotations click to browse term
  CHEBI ontology 19773
    subatomic particle 19771
      composite particle 19771
        hadron 19771
          baryon 19771
            nucleon 19771
              atomic nucleus 19771
                atom 19771
                  main group element atom 19665
                    p-block element atom 19665
                      carbon group element atom 19583
                        carbon atom 19573
                          organic molecular entity 19573
                            organic group 18603
                              organic divalent group 18594
                                organodiyl group 18594
                                  carbonyl group 18507
                                    carbonyl compound 18507
                                      carboxylic ester 15494
                                        lactone 9711
                                          macrocyclic lactone 1747
                                            macrolide 1618
                                              oleandolide 9
                                                3-O-(alpha-L-oleandrosyl)oleandolide 0
                                                3-O-(alpha-L-olivosyl)oleandolide 0
                                                oleandomycin + 9
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