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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-10-23 19:06:15 UTC
HMDB IDHMDB0014325
Secondary Accession Numbers
  • HMDB14325
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
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)butanGenerator
Dihydronorguaiaretic acidHMDB
NDGAHMDB
Nordihydroguaiaretic acidHMDB
Nordihydroguairaretic acidHMDB
meso Nordihydroguaiaretic acidMeSH
Acid, meso-nordihydroguaiareticMeSH
(R*,s*)-4,4'-(2,3-dimethylbutane-1,4-diyl)bispyrocatecholMeSH
Nordihydroguaiaretic acid, (r*,s*)-isomerMeSH
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 KeyHCZKYJDFEPMADG-TXEJJXNPSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassLignans, neolignans and related compounds
Sub ClassDibenzylbutane lignans
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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Biological role:

Indirect biological role:

Physiological effect

Health effect:

  Health condition:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point185.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.014 g/LNot Available
LogP5.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity86.62 m³·mol⁻¹ChemAxon
Polarizability33.63 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-0900000000-c156a7beced7bc5559ceView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004i-1152090000-b4208f8d034e20d028bbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTOF , Positivesplash10-0uyi-0960000000-911fb528895df2fd3880View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0911000000-ad449f20d75c55f665ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0309000000-b0d493df9d2eda6b0f78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0912000000-039497a951e35513d138View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0q29-7930000000-54926d894b8847444c11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-82abdf1a79106e4c83b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0029000000-098dadf437ef798b4f84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-0891000000-bf4e7b7c1a5a632b3968View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00di-0901000000-c0d0caa2c363f17f6c94View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00179 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00179 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
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:15694390 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed: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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]