pyriculol (CHEBI:80728)

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ChEBI Name	pyriculol

ChEBI ID	CHEBI:80728

Definition	A benzaldehyde that is salicylaldehyde which is substituted at position 6 by a (3R,4S,5E)-3,4-dihydroxyhepta-1,5-dien-1-yl group. It is a phytotoxic metabolite, isolated from the rice blast fungi Magnaporthe oryzae and Magnaporthe grisea.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C14H16O4

Net Charge

Average Mass

248.275

Monoisotopic Mass

248.10486

InChI

InChI=1S/C14H16O4/c1-2-4-13(17)14(18)8-7-10-5-3-6-12(16)11(10)9-15/h2-9,13-14,16-18H,1H3/b4-2+,8-7+/t13-,14+/m0/s1

InChIKey

YUQDGJSYYKKISE-COOXUBAGSA-N

SMILES

C=1C=C(C(=C(C1)/C=C/[C@H]([C@H](/C=C/C)O)O)C([H])=O)O

Metabolite of Species	Details
Magnaporthe grisea (NCBI:txid148305)	See: PubMed
Magnaporthe oryzae (NCBI:txid318829)	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.

ChEBI Ontology
Outgoing	pyriculol (CHEBI:80728) has role fungal metabolite (CHEBI:76946) pyriculol (CHEBI:80728) is a benzaldehydes (CHEBI:22698) pyriculol (CHEBI:80728) is a heptaketide (CHEBI:59872) pyriculol (CHEBI:80728) is a homoallylic alcohol (CHEBI:134362) pyriculol (CHEBI:80728) is a phenols (CHEBI:33853) pyriculol (CHEBI:80728) is a secondary allylic alcohol (CHEBI:134396) pyriculol (CHEBI:80728) is a triol (CHEBI:27136)

Incoming	dihydropyriculol (CHEBI:142635) has functional parent pyriculol (CHEBI:80728)

IUPAC Name

2-[(1E,3R,4S,5E)-3,4-dihydroxyhepta-1,5-dien-1-yl]-6-hydroxybenzaldehyde

Synonyms	Sources
2-((1E,5E)-(3R,4S)-3,4-dihydroxy-hepta-1,5-dienyl)-6-hydroxy-benzaldehyde	ChEBI
2-[(1E,3R,4S,5E)-3,4-dihydroxy-1,5-heptadienyl]-6-hydroxybenzaldehyde	ChEBI
pyriculol	UniProt

Registry Number	Type	Source
24868-59-5	CAS Registry Number	ChemIDplus

Last Modified

11 December 2018

General Comment
2018-11-28	Relevant articles: Suzuki, M., Sugiyama, T., Watanabe, M. and Yamashita, K. (1986) Synthesis of optically active pyriculol, a phytotoxic metabolite produced by Pyricularia oryzae Cavara. Agric. Biol. Chem., 50(8), 2159-2160.