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CHEBI:156148 - ascofuranone

Default Structure
ChEBI IDCHEBI:156148
ChEBI Nameascofuranone
Stars
DefinitionA 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.
Last Modified16 July 2020
SubmitterAdnan
DownloadsMolfile
FormulaC23H29ClO5
Net Charge0
Average Mass420.933
Monoisotopic Mass420.17035
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
InChIInChI=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
InChIKeyVGYPZLGWVQQOST-JUERRSSISA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Acremonium sclerotigenum (ncbitaxon:261921) - PubMed (27804952)
Acremonium sp. (ncbitaxon:2046025) - DOI (10.1021/np8006793)
Ascochyta viciae (ncbitaxon:1677696) - PubMed (4792115) Isolated from the filter cake of the fermented broth. Strain: 34
Roles Classification
Biological Roles:
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
antiprotozoal drug  Any antimicrobial drug which is used to treat or prevent protozoal infections.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
angiogenesis inhibitor  An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
antiprotozoal drug  Any antimicrobial drug which is used to treat or prevent protozoal infections.
antilipemic drug  A substance used to treat hyperlipidemia (an excess of lipids in the blood).
ChEBI Ontology
Outgoing Relation(s)
ascofuranone (CHEBI:156148) has role angiogenesis inhibitor (CHEBI:48422)
ascofuranone (CHEBI:156148) has role antilipemic drug (CHEBI:35679)
ascofuranone (CHEBI:156148) has role antineoplastic agent (CHEBI:35610)
ascofuranone (CHEBI:156148) has role antiprotozoal drug (CHEBI:35820)
ascofuranone (CHEBI:156148) has role fungal metabolite (CHEBI:76946)
ascofuranone (CHEBI:156148) is a dihydroxybenzaldehyde (CHEBI:50196)
ascofuranone (CHEBI:156148) is a meroterpenoid (CHEBI:64419)
ascofuranone (CHEBI:156148) is a monochlorobenzenes (CHEBI:83403)
ascofuranone (CHEBI:156148) is a olefinic compound (CHEBI:78840)
ascofuranone (CHEBI:156148) is a resorcinols (CHEBI:33572)
ascofuranone (CHEBI:156148) is a sesquiterpenoid (CHEBI:26658)
ascofuranone (CHEBI:156148) is a tetrahydrofuranone (CHEBI:47016)
ascofuranone (CHEBI:156148) is conjugate acid of ascofuranone(1−) (CHEBI:146160)
Incoming Relation(s)
ascofuranone(1−) (CHEBI:146160) is conjugate base of ascofuranone (CHEBI:156148)
IUPAC Name 
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
Synonyms  Source
ascofuranonChemIDplus
(−)-ascofuranoneChEBI
(S)-ascofuranoneChEBI
(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)-benzaldehydeChemIDplus
Manual XrefsDatabases
AscofuranoneWikipedia
C00017973KNApSAcK
Registry NumbersSources
CAS:38462-04-3ChemIDplus
Citations