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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:ascofuranone
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Accession:CHEBI:156148 term browser browse the term
Definition:A dihydroxybenzaldehyde that is 2,4-dihydroxybenzaldehyde which is substituted by a (2E,6E)-7-[(2S)-5,5-dimethyl-4-oxotetrahydrofuran-2-yl]-3-methylocta-2,6-dien-1-yl group at position 3, chlorine at position 5, and a methyl group at position 6. A meroterpenoid produced by the soil fungus, Acremonium sclerotigenum. It is a promising drug candidate against the tropical disease, African trypanosomiasis.
Synonyms:related_synonym: (S)-ascofuranone;   (S-(E,E))-3-chloro-4,6-dihydroxy-2-methyl-5-(3-methyl-7-(tetrahydro-5,5-dimethyl-4-oxo-2-furanyl)-2,6-octadienyl)-benzaldehyde;   3-chloro-5-{(2E,6E)-7-[(2S)-5,5-dimethyl-4-oxotetrahydrofuran-2-yl]-3-methylocta-2,6-dien-1-yl}-4,6-dihydroxy-2-methylbenzaldehyde;   ascofuranon
 xref: CAS:38462-04-3;   KNApSAcK:C00017973
 xref_mesh: MESH:C006640
 xref: pubmed:10511901;   pubmed:12798927;   pubmed:16288933;   pubmed:17114644;   pubmed:19306296;   pubmed:20460103;   pubmed:20587660;   pubmed:20978157;   pubmed:22580003;   pubmed:23180806;   pubmed:24096035;   pubmed:27804952;   pubmed:28207754;   pubmed:30952781;   pubmed:32439259;   pubmed:32488849;   pubmed:3417568;   pubmed:4792115;   pubmed:8898329;   pubmed:9084049;   wikipedia.en:Ascofuranone
 chemrof_formula: C23H29ClO5
 chemrof_inchi: InChI=1S/C23H29ClO5/c1-13(7-6-8-14(2)18-11-19(26)23(4,5)29-18)9-10-16-21(27)17(12-25)15(3)20(24)22(16)28/h8-9,12,18,27-28H,6-7,10-11H2,1-5H3/b13-9+,14-8+/t18-/m0/s1
 chemrof_inchikey: VGYPZLGWVQQOST-JUERRSSISA-N
 chemrof_smiles: [H]C(=O)c1c(C)c(Cl)c(O)c(C/C=C(C)CC/C=C(C)[C@]2([H])CC(=O)C(C)(C)O2)c1O
 cyclic_relationship: is_conjugate_acid_of CHEBI:146160


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ascofuranone term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Braf B-Raf proto-oncogene, serine/threonine kinase multiple interactions ISO ascofuranone inhibits the reaction [Tetradecanoylphorbol Acetate results in increased phosphorylation of BRAF protein] CTD PMID:17114644 NCBI chr 4:69,329,772...69,476,931
Ensembl chr 4:69,342,813...69,476,931 		JBrowse link
G Fos Fos proto-oncogene, AP-1 transcription factor subunit multiple interactions ISO ascofuranone inhibits the reaction [Tetradecanoylphorbol Acetate results in increased expression of FOS protein] CTD PMID:17114644 NCBI chr 6:110,852,188...110,855,054
Ensembl chr 6:110,852,190...110,855,598 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions ISO ascofuranone inhibits the reaction [Tetradecanoylphorbol Acetate results in increased activity of and results in increased phosphorylation of MAPK1 protein] CTD PMID:17114644 NCBI chr11:97,462,025...97,529,193
Ensembl chr11:97,462,025...97,527,825 		JBrowse link
G Mapk3 mitogen activated protein kinase 3 multiple interactions ISO ascofuranone inhibits the reaction [Tetradecanoylphorbol Acetate results in increased activity of and results in increased phosphorylation of MAPK3 protein] CTD PMID:17114644 NCBI chr 1:190,797,189...190,803,411
Ensembl chr 1:190,797,185...190,803,411 		JBrowse link
G Mmp9 matrix metallopeptidase 9 multiple interactions ISO
EXP 		ascofuranone inhibits the reaction [Tetradecanoylphorbol Acetate results in increased secretion of MMP9 mRNA]; ascofuranone inhibits the reaction [Tetradecanoylphorbol Acetate results in increased secretion of MMP9 protein]; ascofuranone inhibits the reaction [TNF protein results in increased secretion of MMP9 protein] CTD PMID:17114644 NCBI chr 3:174,103,474...174,111,434
Ensembl chr 3:174,084,123...174,111,442 		JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO ascofuranone inhibits the reaction [TNF protein results in increased secretion of MMP9 protein] CTD PMID:17114644 NCBI chr20:3,626,685...3,629,303
Ensembl chr20:3,626,532...3,629,303 		JBrowse link
Term paths to the root
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Term Annotations click to browse term
  CHEBI ontology 20874
    role 20844
      application 20572
        pharmaceutical 20359
          drug 20359
            antineoplastic agent 18082
              ascofuranone 6
Path 2
Term Annotations click to browse term
  CHEBI ontology 20874
    subatomic particle 20883
      composite particle 20883
        hadron 20872
          baryon 20883
            nucleon 20872
              atomic nucleus 20883
                atom 20872
                  main group element atom 20796
                    p-block element atom 20796
                      carbon group element atom 20712
                        carbon atom 20706
                          organic molecular entity 20706
                            heteroorganic entity 20201
                              organochalcogen compound 19822
                                organooxygen compound 19713
                                  carbonyl compound 18827
                                    aldehyde 9206
                                      arenecarbaldehyde 157
                                        benzaldehydes 145
                                          dihydroxybenzaldehyde 23
                                            ascofuranone 6
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