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CHEBI:28869 - menadione

ChEBI IDCHEBI:28869
ChEBI Namemenadione
Stars
DefinitionA member of the class of 1,4-naphthoquinones that is 1,4-naphthoquinone which is substituted at position 2 by a methyl group. It is used as a nutritional supplement and for the treatment of hypoprothrombinemia.
Secondary ChEBI IDsCHEBI:6747, CHEBI:27304, CHEBI:46306
Last Modified26 July 2021
DownloadsMolfile
FormulaC11H8O2
Net Charge0
Average Mass172.183
Monoisotopic Mass172.05243
SMILESCC1=CC(=O)c2ccccc2C1=O
InChIInChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
InChIKeyMJVAVZPDRWSRRC-UHFFFAOYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606) urine (BTO:0001419) PubMed (15722567)
Roles Classification
Biological Roles:
human urinary metabolite  Any metabolite (endogenous or exogenous) found in human urine samples.
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor  An EC 3.4.22.* (cysteine endopeptidase) inhibitor that interferes with the action of SARS coronavirus main proteinase (EC 3.4.22.69).
fat-soluble vitamin (role)  Any vitamin that dissolves in fats and are stored in body tissues. Unlike the water-soluble vitamins, they are stored in the body for long periods of time and generally pose a greater risk for toxicity when consumed in excess.
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
nutraceutical  A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
angiogenesis inhibitor  An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
ChEBI Ontology
Outgoing Relation(s)
menadione (CHEBI:28869) has role angiogenesis inhibitor (CHEBI:48422)
menadione (CHEBI:28869) has role antineoplastic agent (CHEBI:35610)
menadione (CHEBI:28869) has role EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor (CHEBI:147285)
menadione (CHEBI:28869) has role human urinary metabolite (CHEBI:84087)
menadione (CHEBI:28869) has role nutraceutical (CHEBI:50733)
menadione (CHEBI:28869) is a 1,4-naphthoquinones (CHEBI:132142)
menadione (CHEBI:28869) is a vitamin K (CHEBI:28384)
Incoming Relation(s)
menadione sodium sulfonate (CHEBI:63928) has functional parent menadione (CHEBI:28869)
menadione sulfonic acid (CHEBI:63930) has functional parent menadione (CHEBI:28869)
IUPAC Name 
2-methylnaphthalene-1,4-dione
Synonyms  Source
MenadioneKEGG COMPOUND
vitamin K3ChEBI
2-methyl-1,4-naphthoquinoneKEGG COMPOUND
vitamin K3ChemIDplus
2-methylnaphthoquinoneChemIDplus
2-methyl-1,4-naphthalenedioneChemIDplus
Brand Names  Source
KappaxinKEGG DRUG
AquakayChemIDplus
HemodalChemIDplus
AquinoneChemIDplus
UniProt Name  Source
menadioneUniProt
Manual XrefsDatabases
C05377KEGG COMPOUND
VK3PDBeChem
MenadioneWikipedia
DB00170DrugBank
HMDB0001892HMDB
D02335KEGG DRUG
CPD-3766MetaCyc
LSM-3755LINCS
1683DrugCentral
FDB000953FooDB
3915ChemSpider
Registry NumbersSources
Reaxys:1908453Reaxys
CAS:58-27-5KEGG COMPOUND
CAS:58-27-5NIST Chemistry WebBook
CAS:58-27-5ChemIDplus
Citations