Masoprocol (CHEM003770)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (9)XML
Record Information
Version1.0
Creation Date2014-09-11 05:17:43 UTC
Update Date2026-04-02 22:55:50 UTC
Accession NumberCHEM003770
Identification
Common NameMasoprocol
ClassSmall Molecule
DescriptionA potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Antineoplastic Agent
  • Antioxidant
  • Cyclooxygenase Inhibitor
  • Drug
  • Food Toxin
  • Lipoxygenase Inhibitor
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
ActinexChEBI
CHX 100ChEBI
CHX-100ChEBI
Erythro-nordihydroguaiaretic acidChEBI
MasoprocolumChEBI
Meso-1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethylbutaneChEBI
Meso-2,3-bis(3,4-dihydroxyphenylmethyl)butaneChEBI
Meso-4,4'-(2,3-dimethyl-1,4-butanediyl)bis(pyrocatechol)ChEBI
Meso-4,4'-(2,3-dimethyltetramethylene)dipyrocatecholChEBI
Meso-4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diolChEBI
Meso-beta,gamma-dimethyl-alpha,delta-bis(3,4-dihydroxyphenyl)butanChEBI
Meso-ndgaChEBI
Meso-nordihydroguaiaretic acidChEBI
Erythro-nordihydroguaiaretateGenerator
Meso-b,g-dimethyl-a,delta-bis(3,4-dihydroxyphenyl)butanGenerator
Meso-β,γ-dimethyl-α,δ-bis(3,4-dihydroxyphenyl)butanGenerator
Meso-nordihydroguaiaretateGenerator
Meso-b,g-dimethyl-a,δ-bis(3,4-dihydroxyphenyl)butanHMDB
Dihydronorguaiaretic acidHMDB
NDGAHMDB
Nordihydroguaiaretic acidHMDB
Nordihydroguairaretic acidHMDB
Meso nordihydroguaiaretic acidHMDB
Acid, meso-nordihydroguaiareticHMDB
(R*,s*)-4,4'-(2,3-dimethylbutane-1,4-diyl)bispyrocatecholHMDB
Nordihydroguaiaretic acid, (r*,s*)-isomerHMDB
NordihydroguaiaretateHMDB
Chemical FormulaC18H22O4
Average Molecular Mass302.365 g/mol
Monoisotopic Mass302.152 g/mol
CAS Registry Number500-38-9
IUPAC Name4-[(2S,3R)-3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl]benzene-1,2-diol
Traditional Namemasoprocol
SMILESC[C@@H](CC1=CC(O)=C(O)C=C1)[C@H](C)CC1=CC(O)=C(O)C=C1
InChI IdentifierInChI=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+
InChI KeyHCZKYJDFEPMADG-TXEJJXNPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassDibenzylbutane lignans
Sub ClassNot Available
Direct ParentDibenzylbutane lignans
Alternative Parents
Substituents
  • Dibenzylbutane lignan skeleton
  • Phenylpropane
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point185.5°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP3.44ALOGPS
logP4.76ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity86.62 m³·mol⁻¹ChemAxon
Polarizability33.63 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-0900000000-c156a7beced7bc5559ceSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004i-1152090000-b4208f8d034e20d028bbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTOF , Positivesplash10-0uyi-0960000000-911fb528895df2fd3880Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0911000000-ad449f20d75c55f665ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0309000000-b0d493df9d2eda6b0f78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0912000000-039497a951e35513d138Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0q29-7930000000-54926d894b8847444c11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-82abdf1a79106e4c83b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0029000000-098dadf437ef798b4f84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-0891000000-bf4e7b7c1a5a632b3968Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0219000000-68686370b80d2d5b8f67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fr-4910000000-8c3f799ce8c8c7964379Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-5960000000-56ed4c425972dd72714fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-65d407b0c8387d27535dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0395000000-159905151a93ed0a844cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xr-3970000000-78d852a0cf5c2bc9adc5Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-0901000000-c0d0caa2c363f17f6c94Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureLess than 1%-2% is absorbed through the skin over a 4-day period following application.
Mechanism of ToxicityAlthough the exact mechanism of action is not known, studies have shown that masoprocol is a potent 5-lipoxygenase inhibitor and has antiproliferative activity against keratinocytes in tissue culture, but the relationship between this activity and its effectiveness in actinic keratoses is unknown. Masoprocol also inhibits prostaglandins but the significance of this action is not yet known.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed for the treatment of actinic keratoses (precancerous skin growths that can become malignant if left untreated).
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose or allergic reaction include bluish coloration of skin, dizziness, severe, or feeling faint, wheezing or trouble in breathing.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00179
HMDB IDHMDB0014325
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00000693
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMasoprocol
Chemspider ID64490
ChEBI ID73468
PubChem Compound ID71398
Kegg Compound IDC10719
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10027587
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10206430
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=10411373
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=10950827
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11016888
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15814253
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=18672930
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=1869646
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=8040425
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=8412980
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=9169274
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=9617755