CHEBI:66424 - myrothenone A

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ChEBI Name myrothenone A
ChEBI ID CHEBI:66424
Definition An 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).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C8H9NO3
Net Charge 0
Average Mass 167.16200
Monoisotopic Mass 167.05824
InChI InChI=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
InChIKey PGQRZOUYTNKEBE-QMMMGPOBSA-N
SMILES O[C@]1(CC(NC=O)=CC1=O)C=C
Metabolite of Species Details
Myrothecium (NCBI:txid5531) See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 α-hydroxy ketone (CHEBI:139592)
myrothenone A (CHEBI:66424) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
N-[(4R)-4-ethenyl-4-hydroxy-3-oxocyclopent-1-en-1-yl]formamide
Synonyms Sources
(5R)-5-ethenyl-3-formamido-5-hydroxy-2-cyclopenten-1-one ChEBI
N-[(4R)-4-hydroxy-3-oxo-4-vinylcyclopent-1-en-1-yl]formamide IUPAC
Registry Number Type Source
10064379 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15802853 PubMed citation Europe PMC
Last Modified
07 February 2018