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CHEBI:73468 - masoprocol

ChEBI IDCHEBI:73468
ChEBI Namemasoprocol
Stars
DefinitionThe meso-form of nordihydroguaiaretic acid. An antioxidant found in the creosote bush, Larrea divaricata, it is a potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. It also inhibits (though to a lesser extent) formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase.
Last Modified22 February 2017
SubmitterGareth Owen
DownloadsMolfile
FormulaC18H22O4
Net Charge0
Average Mass302.370
Monoisotopic Mass302.15181
SMILESC[C@H](Cc1ccc(O)c(O)c1)[C@@H](C)Cc1ccc(O)c(O)c1
InChIInChI=1S/C18H22O4/c1-11(7-13-3-5-15(19)17(21)9-13)12(2)8-14-4-6-16(20)18(22)10-14/h3-6,9-12,19-22H,7-8H2,1-2H3/t11-,12+
InChIKeyHCZKYJDFEPMADG-TXEJJXNPSA-N
Wikipedia
Roles Classification
Chemical Role:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
lipoxygenase inhibitor  A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.
ferroptosis inhibitor  Any substance that inhibits the process of ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:
hypoglycemic agent  A drug which lowers the blood glucose level.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
ChEBI Ontology
Outgoing Relation(s)
masoprocol (CHEBI:73468) has role antineoplastic agent (CHEBI:35610)
masoprocol (CHEBI:73468) has role hypoglycemic agent (CHEBI:35526)
masoprocol (CHEBI:73468) has role lipoxygenase inhibitor (CHEBI:35856)
masoprocol (CHEBI:73468) has role metabolite (CHEBI:25212)
masoprocol (CHEBI:73468) is a nordihydroguaiaretic acid (CHEBI:7625)
IUPAC Name 
4-[(2R,3S)-4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
INNs  Source
masoprocolChemIDplus
masoprocolWHO MedNet
masoprocolumChemIDplus
masoprocolWHO MedNet
Synonyms  Source
meso-nordihydroguaiaretic acidKEGG DRUG
meso-4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diolChEBI
CHX 100ChemIDplus
erythro-nordihydroguaiaretic acidChEBI
meso-NDGAChEBI
CHX-100ChemIDplus
Brand Name  Source
ActinexChemIDplus
Manual XrefsDatabases
D04862KEGG DRUG
MasoprocolWikipedia
DB00179DrugBank
HMDB0014325HMDB
C10719KEGG COMPOUND
C00000693KNApSAcK
1637DrugCentral
Registry NumbersSources
Reaxys:9874298Reaxys
Reaxys:2056826Reaxys
CAS:27686-84-6ChemIDplus
CAS:500-38-9KEGG COMPOUND
Citations