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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:34 UTC
HMDB IDHMDB0014325
Secondary Accession Numbers
  • HMDB0012270
  • HMDB12270
  • HMDB14325
Metabolite Identification
Common NameMasoprocol
DescriptionMasoprocol, also known as actinex or meso-ndga, belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety. Symptoms of overdose or allergic reaction include bluish coloration of skin, dizziness, or feeling faint, wheezing or trouble in breathing. Masoprocol also inhibits prostaglandins but the significance of this action is not yet known. Masoprocol is a drug which is used for the treatment of actinic keratoses (precancerous skin growths that can become malignant if left untreated). It also serves as an antioxidant in fats and oils. Masoprocol is a potentially toxic compound. It is not known exactly how masoprocol works. 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. A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism.
Structure
Data?1582753165
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 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 Number27686-84-6
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
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point185.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.014 g/LNot Available
LogP5.8Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+172.25531661259
DarkChem[M-H]-172.70731661259
DeepCCS[M+H]+179.24230932474
DeepCCS[M-H]-176.88430932474
DeepCCS[M-2H]-210.77330932474
DeepCCS[M+Na]+186.00130932474
AllCCS[M+H]+174.232859911
AllCCS[M+H-H2O]+170.732859911
AllCCS[M+NH4]+177.632859911
AllCCS[M+Na]+178.532859911
AllCCS[M-H]-176.432859911
AllCCS[M+Na-2H]-176.332859911
AllCCS[M+HCOO]-176.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MasoprocolC[C@@H](CC1=CC(O)=C(O)C=C1)[C@H](C)CC1=CC(O)=C(O)C=C14841.8Standard polar33892256
MasoprocolC[C@@H](CC1=CC(O)=C(O)C=C1)[C@H](C)CC1=CC(O)=C(O)C=C12890.6Standard non polar33892256
MasoprocolC[C@@H](CC1=CC(O)=C(O)C=C1)[C@H](C)CC1=CC(O)=C(O)C=C13023.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Masoprocol,1TMS,isomer #1C[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)[C@H](C)CC1=CC=C(O)C(O)=C12832.1Semi standard non polar33892256
Masoprocol,1TMS,isomer #2C[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)[C@H](C)CC1=CC=C(O)C(O)=C12833.6Semi standard non polar33892256
Masoprocol,1TMS,isomer #3C[C@@H](CC1=CC=C(O)C(O)=C1)[C@H](C)CC1=CC=C(O)C(O[Si](C)(C)C)=C12832.1Semi standard non polar33892256
Masoprocol,1TMS,isomer #4C[C@@H](CC1=CC=C(O)C(O)=C1)[C@H](C)CC1=CC=C(O[Si](C)(C)C)C(O)=C12833.6Semi standard non polar33892256
Masoprocol,2TMS,isomer #1C[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[C@H](C)CC1=CC=C(O)C(O)=C12733.2Semi standard non polar33892256
Masoprocol,2TMS,isomer #2C[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)[C@H](C)CC1=CC=C(O[Si](C)(C)C)C(O)=C12719.6Semi standard non polar33892256
Masoprocol,2TMS,isomer #3C[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)[C@H](C)CC1=CC=C(O)C(O[Si](C)(C)C)=C12702.8Semi standard non polar33892256
Masoprocol,2TMS,isomer #4C[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)[C@H](C)CC1=CC=C(O[Si](C)(C)C)C(O)=C12753.6Semi standard non polar33892256
Masoprocol,2TMS,isomer #5C[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)[C@H](C)CC1=CC=C(O)C(O[Si](C)(C)C)=C12719.6Semi standard non polar33892256
Masoprocol,2TMS,isomer #6C[C@@H](CC1=CC=C(O)C(O)=C1)[C@H](C)CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12733.2Semi standard non polar33892256
Masoprocol,3TMS,isomer #1C[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[C@H](C)CC1=CC=C(O[Si](C)(C)C)C(O)=C12749.6Semi standard non polar33892256
Masoprocol,3TMS,isomer #2C[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[C@H](C)CC1=CC=C(O)C(O[Si](C)(C)C)=C12740.7Semi standard non polar33892256
Masoprocol,3TMS,isomer #3C[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)[C@H](C)CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12740.7Semi standard non polar33892256
Masoprocol,3TMS,isomer #4C[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)[C@H](C)CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12749.6Semi standard non polar33892256
Masoprocol,4TMS,isomer #1C[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[C@H](C)CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12792.2Semi standard non polar33892256
Masoprocol,1TBDMS,isomer #1C[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)[C@H](C)CC1=CC=C(O)C(O)=C13113.7Semi standard non polar33892256
Masoprocol,1TBDMS,isomer #2C[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)[C@H](C)CC1=CC=C(O)C(O)=C13130.8Semi standard non polar33892256
Masoprocol,1TBDMS,isomer #3C[C@@H](CC1=CC=C(O)C(O)=C1)[C@H](C)CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C13113.7Semi standard non polar33892256
Masoprocol,1TBDMS,isomer #4C[C@@H](CC1=CC=C(O)C(O)=C1)[C@H](C)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C13130.8Semi standard non polar33892256
Masoprocol,2TBDMS,isomer #1C[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[C@H](C)CC1=CC=C(O)C(O)=C13266.9Semi standard non polar33892256
Masoprocol,2TBDMS,isomer #2C[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)[C@H](C)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C13286.2Semi standard non polar33892256
Masoprocol,2TBDMS,isomer #3C[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)[C@H](C)CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C13262.5Semi standard non polar33892256
Masoprocol,2TBDMS,isomer #4C[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)[C@H](C)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C13315.6Semi standard non polar33892256
Masoprocol,2TBDMS,isomer #5C[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)[C@H](C)CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C13286.2Semi standard non polar33892256
Masoprocol,2TBDMS,isomer #6C[C@@H](CC1=CC=C(O)C(O)=C1)[C@H](C)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C13266.9Semi standard non polar33892256
Masoprocol,3TBDMS,isomer #1C[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[C@H](C)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C13469.8Semi standard non polar33892256
Masoprocol,3TBDMS,isomer #2C[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[C@H](C)CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C13441.8Semi standard non polar33892256
Masoprocol,3TBDMS,isomer #3C[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)[C@H](C)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C13441.8Semi standard non polar33892256
Masoprocol,3TBDMS,isomer #4C[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)[C@H](C)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C13469.8Semi standard non polar33892256
Masoprocol,4TBDMS,isomer #1C[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[C@H](C)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C13623.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Masoprocol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-0900000000-c156a7beced7bc5559ce2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Masoprocol GC-MS (4 TMS) - 70eV, Positivesplash10-004i-1152090000-b4208f8d034e20d028bb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Masoprocol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-0901000000-c0d0caa2c363f17f6c942014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Masoprocol LC-ESI-qTOF , Positive-QTOFsplash10-0uyi-0960000000-911fb528895df2fd38802017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Masoprocol , positive-QTOFsplash10-00di-0911000000-ad449f20d75c55f665cc2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masoprocol 10V, Positive-QTOFsplash10-0udi-0309000000-b0d493df9d2eda6b0f782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masoprocol 20V, Positive-QTOFsplash10-0uk9-0912000000-039497a951e35513d1382016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masoprocol 40V, Positive-QTOFsplash10-0q29-7930000000-54926d894b8847444c112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masoprocol 10V, Negative-QTOFsplash10-0udi-0009000000-82abdf1a79106e4c83b02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masoprocol 20V, Negative-QTOFsplash10-0udi-0029000000-098dadf437ef798b4f842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masoprocol 40V, Negative-QTOFsplash10-0a4r-0891000000-bf4e7b7c1a5a632b39682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masoprocol 10V, Positive-QTOFsplash10-0udi-0219000000-68686370b80d2d5b8f672021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masoprocol 20V, Positive-QTOFsplash10-00fr-4910000000-8c3f799ce8c8c79643792021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masoprocol 40V, Positive-QTOFsplash10-00xr-5960000000-56ed4c425972dd72714f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masoprocol 10V, Negative-QTOFsplash10-0udi-0009000000-65d407b0c8387d27535d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masoprocol 20V, Negative-QTOFsplash10-0udi-0395000000-159905151a93ed0a844c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Masoprocol 40V, Negative-QTOFsplash10-00xr-3970000000-78d852a0cf5c2bc9adc52021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00179 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00179 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00179
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00000693
Chemspider ID64490
KEGG Compound IDC10719
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMasoprocol
METLIN IDNot Available
PubChem Compound71398
PDB IDNot Available
ChEBI ID73468
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]