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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:28:06 UTC
HMDB IDHMDB14325
Secondary Accession NumbersNone
Metabolite Identification
Common NameMasoprocol
DescriptionMasoprocol is only found in individuals that have used or taken this drug.Although 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.
Structure
Thumb
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
Dihydronorguaiaretic acidHMDB
NDGAHMDB
Nordihydroguaiaretic acidHMDB
Nordihydroguairaretic acidHMDB
Chemical FormulaC18H22O4
Average Molecular Weight302.3649
Monoisotopic Molecular Weight302.151809192
IUPAC Name4-[(2S,3R)-3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl]benzene-1,2-diol
Traditional Namemasoprocol
CAS Registry Number500-38-9
SMILES
C[C@@H](CC1=CC(O)=C(O)C=C1)[C@H](C)CC1=CC(O)=C(O)C=C1
InChI Identifier
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+
InChI KeyInChIKey=HCZKYJDFEPMADG-TXEJJXNPSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • 1,2-diphenol
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antineoplastics, topical
  • Antioxidants
  • Cyclooxygenase Inhibitors
  • Keratolytic Agents
  • Lipoxygenase Inhibitors
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point185.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.36e-02 g/LNot Available
LogP5.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 mg/mLALOGPS
logP3.44ALOGPS
logP4.76ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity86.62 m3·mol-1ChemAxon
Polarizability33.63 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-00di-0901000000-c0d0caa2c363f17f6c94View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00179
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00179
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00179
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID64490
KEGG Compound IDC10719
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMasoprocol
NuGOwiki LinkHMDB14325
Metagene LinkHMDB14325
METLIN IDNot Available
PubChem Compound71398
PDB IDNot Available
ChEBI ID244744
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in metal ion binding
Specific function:
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:
ALOX5
Uniprot ID:
P09917
Molecular weight:
77982.595
References
  1. Audouin C, Mestdagh N, Lassoie MA, Houssin R, Henichart JP: N-Aminoindoline derivatives as inhibitors of 5-lipoxygenase. Bioorg Med Chem Lett. 2001 Mar 26;11(6):845-8. [11277534 ]
  2. Lambert JD, Meyers RO, Timmermann BN, Dorr RT: Pharmacokinetic analysis by high-performance liquid chromatography of intravenous nordihydroguaiaretic acid in the mouse. J Chromatogr B Biomed Sci Appl. 2001 Apr 15;754(1):85-90. [11318430 ]
  3. Azadzoi KM, Heim VK, Tarcan T, Siroky MB: Alteration of urothelial-mediated tone in the ischemic bladder: role of eicosanoids. Neurourol Urodyn. 2004;23(3):258-64. [15098224 ]
  4. West M, Mhatre M, Ceballos A, Floyd RA, Grammas P, Gabbita SP, Hamdheydari L, Mai T, Mou S, Pye QN, Stewart C, West S, Williamson KS, Zemlan F, Hensley K: The arachidonic acid 5-lipoxygenase inhibitor nordihydroguaiaretic acid inhibits tumor necrosis factor alpha activation of microglia and extends survival of G93A-SOD1 transgenic mice. J Neurochem. 2004 Oct;91(1):133-43. [15379894 ]
  5. Jeon SB, Ji KA, You HJ, Kim JH, Jou I, Joe EH: Nordihydroguaiaretic acid inhibits IFN-gamma-induced STAT tyrosine phosphorylation in rat brain astrocytes. Biochem Biophys Res Commun. 2005 Mar 11;328(2):595-600. [15694390 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
General function:
Involved in monooxygenase activity
Specific function:
This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible for the epoxidation of endogenous cardiac arachidonic acid pools.
Gene Name:
CYP2J2
Uniprot ID:
P51589
Molecular weight:
57610.165
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. [19934256 ]