CHEBI:73468 - masoprocol

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ChEBI Name masoprocol
ChEBI ID CHEBI:73468
Definition The 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H22O4
Net Charge 0
Average Mass 302.36490
InChI InChI=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+
InChIKey HCZKYJDFEPMADG-TXEJJXNPSA-N
SMILES C[C@@H](Cc1ccc(O)c(O)c1)[C@H](C)Cc1ccc(O)c(O)c1
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.
(via nordihydroguaiaretic acid )
Biological Role(s): 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.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via nordihydroguaiaretic acid )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
hypoglycemic agent
A drug which lowers the blood glucose level.
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ChEBI Ontology
Outgoing 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 Sources
masoprocol WHO MedNet
masoprocol WHO MedNet
masoprocol ChemIDplus
masoprocolum ChemIDplus
Synonyms Sources
CHX 100 ChemIDplus
CHX-100 ChemIDplus
erythro-nordihydroguaiaretic acid ChEBI
meso-1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane ChEBI
meso-2,3-bis(3,4-dihydroxyphenylmethyl)butane ChEBI
meso-4,4'-(2,3-dimethyl-1,4-butanediyl)bis(pyrocatechol) ChEBI
meso-4,4'-(2,3-dimethyltetramethylene)dipyrocatechol ChEBI
meso-4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol ChEBI
meso-β,γ-dimethyl-α,δ-bis(3,4-dihydroxyphenyl)butan ChEBI
meso-NDGA ChEBI
meso-nordihydroguaiaretic acid KEGG DRUG
Brand Name Source
Actinex ChemIDplus
Database Links Databases
C00000693 KNApSAcK
C10719 KEGG COMPOUND
D04862 KEGG DRUG
DB00179 DrugBank
HMDB14325 HMDB
Masoprocol Wikipedia
View more database links
Registry Numbers Types Sources
2056826 Reaxys Registry Number Reaxys
27686-84-6 CAS Registry Number ChemIDplus
500-38-9 CAS Registry Number KEGG COMPOUND
9874298 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10027587 PubMed citation CiteXplore
10206430 PubMed citation CiteXplore
10411373 PubMed citation CiteXplore
10950827 PubMed citation CiteXplore
11016888 PubMed citation CiteXplore
15814253 PubMed citation CiteXplore
18672930 PubMed citation CiteXplore
1869646 PubMed citation CiteXplore
8040425 PubMed citation CiteXplore
8412980 PubMed citation CiteXplore
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9617755 PubMed citation CiteXplore
Last Modified
28 July 2014