CHEBI:146279 - ascofuranol

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ChEBI Name ascofuranol
ChEBI ID CHEBI:146279
Definition A dihydroxybenzaldehyde that is 2,4-dihydroxybenzaldehyde which is substituted by a {(2E,6E)-7-[(2S,4S)-4-hydroxy-5,5-dimethyltetrahydrofuran-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 various filamentous fungi, including Acremonium egyptiacum.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C23H31ClO5
Net Charge 0
Average Mass 422.950
Monoisotopic Mass 422.18600
InChI InChI=1S/C23H31ClO5/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/h8-9,12,18-19,26-28H,6-7,10-11H2,1-5H3/b13-9+,14-8+/t18-,19-/m0/s1
InChIKey YHXSUSPTGLHIRR-UZFWGDPLSA-N
SMILES C=1(C(=C(C(=C(C1Cl)C)C=O)O)C/C=C(/CC/C=C(\C)/[C@@]2(C[C@@H](C(O2)(C)C)O)[H])\C)O
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via meroterpenoid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ascofuranol (CHEBI:146279) is a dihydroxybenzaldehyde (CHEBI:50196)
ascofuranol (CHEBI:146279) is a meroterpenoid (CHEBI:64419)
ascofuranol (CHEBI:146279) is a monochlorobenzenes (CHEBI:83403)
ascofuranol (CHEBI:146279) is a monohydroxytetrahydrofuran (CHEBI:47018)
ascofuranol (CHEBI:146279) is a olefinic compound (CHEBI:78840)
ascofuranol (CHEBI:146279) is a resorcinols (CHEBI:33572)
ascofuranol (CHEBI:146279) is a sesquiterpenoid (CHEBI:26658)
ascofuranol (CHEBI:146279) is conjugate acid of ascofuranol(1−) (CHEBI:146159)
Incoming ascofuranol(1−) (CHEBI:146159) is conjugate base of ascofuranol (CHEBI:146279)
IUPAC Name
3-chloro-4,6-dihydroxy-5-{(2E,6E)-7-[(2S,4S)-4-hydroxy-5,5-dimethyltetrahydrofuran-2-yl]-3-methylocta-2,6-dien-1-yl}-2-methylbenzaldehyde
Synonyms Sources
(−)-ascofuranol ChEBI
(2'E,6'E,1'S,4'S )-(−)-5-chloro-2,4-dihydroxy-6-methyl-3-[7'-(3',3'-dimethyl-4'-hydroxy-2'-oxacyclopentyl)-3',7'-dimethyl-2',6'-hepta-dienyl]benzaldehyde ChEBI
(2S-(2α(2E,6E),4α))-3-chloro-4,6-dihydroxy-2-methyl-5-(3-methyl-7-(tetrahydro-4-hydroxy-5,5-dimethyl-2-furanyl)-2,6-octadienyl)-benzaldehyde ChemIDplus
Manual Xref Database
C00017974 KNApSAcK
View more database links
Registry Number Type Source
51759-79-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15032480 PubMed citation Europe PMC
30952781 PubMed citation SUBMITTER
Last Modified
09 March 2020
General Comment
2020-03-09 For synthesis of the natural [(−)-]enantiomer see Tetrahedron, 1985, v41(15), 3049-3062.