CHEBI:146008 - semiviriditoxin

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ChEBI Name semiviriditoxin
ChEBI ID CHEBI:146008
Definition A naphthopyran that is 3,4-dihydro-naphtho[2,3-c]pyran-1-one which is substituted by a 2-methoxy-2-oxoethyl group at position 3, a methoxy group at position 7, and hydroxy groups at positions 9 and 10 (the 3S enantiomer). It is produced by the fungus Paecilomyces variotii, isolated from the larvae of the mountain pine beetle Dendroctonus ponderosae. The biological precursor of viriditoxin.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
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Formula C17H16O7
Net Charge 0
Average Mass 332.308
Monoisotopic Mass 332.08960
InChI InChI=1S/C17H16O7/c1-22-10-4-8-3-9-5-11(7-13(19)23-2)24-17(21)15(9)16(20)14(8)12(18)6-10/h3-4,6,11,18,20H,5,7H2,1-2H3/t11-/m0/s1
InChIKey CVDVPYTVGZWTON-NSHDSACASA-N
SMILES C=12C(=C3C(=CC(=CC3=CC1C[C@H](OC2=O)CC(OC)=O)OC)O)O
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.
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ChEBI Ontology
Outgoing semiviriditoxin (CHEBI:146008) has role fungal metabolite (CHEBI:76946)
semiviriditoxin (CHEBI:146008) is a δ-lactone (CHEBI:18946)
semiviriditoxin (CHEBI:146008) is a heptaketide (CHEBI:59872)
semiviriditoxin (CHEBI:146008) is a methyl ester (CHEBI:25248)
semiviriditoxin (CHEBI:146008) is a naphtho-α-pyrone (CHEBI:146280)
semiviriditoxin (CHEBI:146008) is a phenols (CHEBI:33853)
Incoming (M)-viriditoxin (CHEBI:146007) has functional parent semiviriditoxin (CHEBI:146008)
(P)-viriditoxin (CHEBI:146016) has functional parent semiviriditoxin (CHEBI:146008)
IUPAC Name
methyl [(3S)-9,10-dihydroxy-7-methoxy-1-oxo-3,4-dihydro-1H-naphtho[2,3-c]pyran-3-yl]acetate
Synonym Source
semiviriditoxin UniProt
Citation Waiting for Citations Type Source
31045362 PubMed citation SUBMITTER
Last Modified
14 April 2022
General Comment
2020-02-06 This is compound 10 in pmid:31045362. For a total synthesis, see Tetrahedron, 1009, v65, pp 4007-4012