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CHEBI:133841 - yanuthone D

Default Structure
ChEBI IDCHEBI:133841
ChEBI Nameyanuthone D
Stars
DefinitionA 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.
Last Modified22 November 2016
SubmitterJubra
DownloadsMolfile
FormulaC28H38O8
Net Charge0
Average Mass502.604
Monoisotopic Mass502.25667
SMILESCC(C)=CCC/C(C)=C/CC/C(C)=C/C[C@@]12O[C@@H]1C(=O)C(COC(=O)CC(C)(O)CC(=O)O)=CC2=O
InChIInChI=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
InChIKeyNIBXHVDVUJEQPO-MHVGILDJSA-N
Species of MetaboliteComponentSourceComments
Aspergillus niger ATCC 1015 (ncbitaxon:380704) - PubMed (24684908)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
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 NumbersSources
Reaxys:8741127Reaxys
Citations