CHEBI:156148 - ascofuranone

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ChEBI Name ascofuranone
ChEBI ID CHEBI:156148
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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C23H29ClO5
Net Charge 0
Average Mass 420.930
Monoisotopic Mass 420.17035
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
InChIKey VGYPZLGWVQQOST-JUERRSSISA-N
SMILES C=1(C(=C(C(=C(C1Cl)C)C([H])=O)O)C/C=C(/CC/C=C(\C)/[C@@]2(CC(C(O2)(C)C)=O)[H])\C)O
Metabolite of Species Details
Ascochyta viciae (NCBI:txid1677696) Isolated from the filter cake of the fermented broth. of strain 34 See: PubMed
Acremonium sp. (NCBI:txid2046025) See: DOI
Acremonium sclerotigenum (NCBI:txid261921) See: PubMed
Roles Classification
Biological Role(s): 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.
(via meroterpenoid )
Application(s): 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.
antilipemic drug
A substance used to treat hyperlipidemia (an excess of lipids in the blood).
antiprotozoal drug
Any antimicrobial drug which is used to treat or prevent protozoal infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
(−)-ascofuranone ChEBI
(S)-ascofuranone ChEBI
(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 ChemIDplus
ascofuranon ChemIDplus
Manual Xrefs Databases
Ascofuranone Wikipedia
C00017973 KNApSAcK
View more database links
Registry Number Type Source
38462-04-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10511901 PubMed citation Europe PMC
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Last Modified
16 July 2020