CHEBI:66424 - myrothenone A

ChEBI IDCHEBI:66424
ChEBI Namemyrothenone A
Stars
DefinitionAn alicyclic ketone which is 3-oxocyclopent-1-ene substituted by a formamido group at position 1 as well as vinyl and hydroxy groups at position 4. It is isolated from a marine derived fungus Myrothecium sp. and acts as an inhibitor of tyrosinase enzyme (EC 1.14.18.1).
Last Modified7 February 2018
DownloadsMolfile
FormulaC8H9NO3
Net Charge0
Average Mass167.164
Monoisotopic Mass167.05824
SMILESC=C[C@]1(O)CC(NC=O)=CC1=O
InChIInChI=1S/C8H9NO3/c1-2-8(12)4-6(9-5-10)3-7(8)11/h2-3,5,12H,1,4H2,(H,9,10)/t8-/m0/s1
InChIKeyPGQRZOUYTNKEBE-QMMMGPOBSA-N
Species of MetaboliteComponentSourceComments
Myrothecium (ncbitaxon:5531) - PubMed (15802853)
Roles Classification
Biological Roles:
EC 1.14.18.1 (tyrosinase) inhibitor  Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.
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)
myrothenone A (CHEBI:66424) has role EC 1.14.18.1 (tyrosinase) inhibitor (CHEBI:59997)
myrothenone A (CHEBI:66424) has role metabolite (CHEBI:25212)
myrothenone A (CHEBI:66424) is a alicyclic ketone (CHEBI:36132)
myrothenone A (CHEBI:66424) is a formamides (CHEBI:24079)
myrothenone A (CHEBI:66424) is a tertiary alcohol (CHEBI:26878)
myrothenone A (CHEBI:66424) is a tertiary α-hydroxy ketone (CHEBI:139592)
IUPAC Name 
N-[(4R)-4-ethenyl-4-hydroxy-3-oxocyclopent-1-en-1-yl]formamide
Synonyms  Source
N-[(4R)-4-hydroxy-3-oxo-4-vinylcyclopent-1-en-1-yl]formamideIUPAC
(5R)-5-ethenyl-3-formamido-5-hydroxy-2-cyclopenten-1-oneChEBI
Registry NumbersSources
Reaxys:10064379Reaxys
Citations