CHEBI:133841 - yanuthone D

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ChEBI Name yanuthone D
ChEBI ID CHEBI:133841
Definition A class I yanuthone that is yanuthone E in which the secondary hydroxy group has been oxidised to the corresponding ketone. It is the only one of the sixteen yanuthones described up to 2015 to display strong antimicrobial activity.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Julian Brandl
Supplier Information
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Formula C28H38O8
Net Charge 0
Average Mass 502.598
Monoisotopic Mass 502.25667
InChI InChI=1S/C28H38O8/c1-18(2)8-6-9-19(3)10-7-11-20(4)12-13-28-22(29)14-21(25(33)26(28)36-28)17-35-24(32)16-27(5,34)15-23(30)31/h8,10,12,14,26,34H,6-7,9,11,13,15-17H2,1-5H3,(H,30,31)/b19-10+,20-12+/t26-,27?,28+/m1/s1
InChIKey NIBXHVDVUJEQPO-MHVGILDJSA-N
SMILES C/C(=C\CC\C(\C)=C\C[C@]12C(C=C(C([C@H]1O2)=O)COC(CC(CC(O)=O)(O)C)=O)=O)/CCC=C(C)C
Metabolite of Species Details
Aspergillus niger ATCC 1015 (NCBI:txid380704) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): Aspergillus metabolite
Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
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 yanuthone D (CHEBI:133841) has functional parent 3-hydroxy-3-methylglutaric acid (CHEBI:16831)
yanuthone D (CHEBI:133841) has functional parent yanuthone E (CHEBI:133840)
yanuthone D (CHEBI:133841) has role Aspergillus metabolite (CHEBI:76956)
yanuthone D (CHEBI:133841) has role antifungal agent (CHEBI:35718)
yanuthone D (CHEBI:133841) is a class I yanuthone (CHEBI:133075)
yanuthone D (CHEBI:133841) is a dicarboxylic acid monoester (CHEBI:36244)
yanuthone D (CHEBI:133841) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
5-({(1S,6R)-2,5-dioxo-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-hydroxy-3-methyl-5-oxopentanoic acid
Registry Number Type Source
8741127 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11031048 PubMed citation Europe PMC
24684908 PubMed citation Europe PMC
25293978 PubMed citation Europe PMC
26729047 PubMed citation Europe PMC
Last Modified
22 November 2016