NP-MRD: Showing NP-Card for Masoprocol (NP0000508)

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Record Information

Version

2.0

Created at

2012-09-06 15:16:49 UTC

Updated at

2024-09-03 04:22:22 UTC

NP-MRD ID

NP0000508

Natural Product DOI

https://doi.org/10.57994/2832

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Masoprocol

Description

Masoprocol, 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

MOL SDF PDB SMILES InChI


  Mrv1652305271900202D          

 22 23  0  0  0  0            999 V2000
10001.0610 9999.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.346410000.2157    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6335 9999.8034    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.920110000.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4913 9997.7449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0667 9998.5686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6335 9998.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.346410001.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.488210002.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.913210001.4513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.492710000.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7783 9999.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7783 9998.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4927 9998.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2072 9998.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2072 9999.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.202010001.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.487510001.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.773010001.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.772910000.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.4874 9999.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.202010000.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  1  0  0  0
  3  4  1  0  0  0  0
  3  7  1  6  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 11  1  0  0  0  0
 13  6  1  0  0  0  0
 14  5  1  0  0  0  0
  4 16  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 17  1  0  0  0  0
 17 10  1  0  0  0  0
 18  9  1  0  0  0  0
  1 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000508

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
HCZKYJDFEPMADG-TXEJJXNPSA-N

> <FORMULA>
C18H22O4

> <MOLECULAR_WEIGHT>
302.3649

> <EXACT_MASS>
302.151809192

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
33.629093382907094

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2S,3R)-3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl]benzene-1,2-diol

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
4.758522743999999

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.808299093340917

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.206546692580925

> <JCHEM_PKA_STRONGEST_BASIC>
-6.25042985340511

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
86.619

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
masoprocol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8668.6478666.300   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.3138667.069   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.9838666.300   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8664.6518667.069   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8661.9848662.457   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8659.3258663.995   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8665.9838664.762   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8667.3138668.607   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8671.3118670.913   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8673.9718669.376   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8661.9868667.071   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8660.6538666.301   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8660.6538664.761   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8661.9868663.991   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.3208664.761   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.3208666.301   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8672.6448668.608   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8671.3108669.378   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8669.9768668.608   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8669.9768667.068   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8671.3108666.298   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8672.6448667.068   0.000  0.00  0.00           C+0
CONECT    1    2   20                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3   16                                                       
CONECT    5   14                                                            
CONECT    6   13                                                            
CONECT    7    3                                                            
CONECT    8    2                                                            
CONECT    9   18                                                            
CONECT   10   17                                                            
CONECT   11   12   16                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14    6                                                  
CONECT   14   13   15    5                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11    4                                                  
CONECT   17   18   22   10                                                  
CONECT   18   17   19    9                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21    1                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
Actinex	ChEBI
CHX 100	ChEBI
CHX-100	ChEBI
Erythro-nordihydroguaiaretic acid	ChEBI
Masoprocolum	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-beta,gamma-dimethyl-alpha,delta-bis(3,4-dihydroxyphenyl)butan	ChEBI
Meso-ndga	ChEBI
Meso-nordihydroguaiaretic acid	ChEBI
Erythro-nordihydroguaiaretate	Generator
Meso-b,g-dimethyl-a,delta-bis(3,4-dihydroxyphenyl)butan	Generator
Meso-β,γ-dimethyl-α,δ-bis(3,4-dihydroxyphenyl)butan	Generator
Meso-nordihydroguaiaretate	Generator
Meso-b,g-dimethyl-a,δ-bis(3,4-dihydroxyphenyl)butan	HMDB
Dihydronorguaiaretic acid	HMDB
NDGA	HMDB
Nordihydroguaiaretic acid	HMDB
Nordihydroguairaretic acid	HMDB
Meso nordihydroguaiaretic acid	HMDB
Acid, meso-nordihydroguaiaretic	HMDB
(R,s)-4,4'-(2,3-dimethylbutane-1,4-diyl)bispyrocatechol	HMDB
Nordihydroguaiaretic acid, (r,s)-isomer	HMDB
Nordihydroguaiaretate	HMDB

Chemical Formula

C₁₈H₂₂O₄

Average Mass

302.3649 Da

Monoisotopic Mass

302.15181 Da

IUPAC Name

4-[(2S,3R)-3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl]benzene-1,2-diol

Traditional Name

masoprocol

CAS Registry Number

27686-84-6

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 Key

HCZKYJDFEPMADG-TXEJJXNPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-17	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Guaiacum officinale	Plant	KNApSAcK
Guaiacum sanctum	Plant	KNApSAcK
Guajacum officinale	-	KNApSAcK
Larrea divaricata	Plant	KNApSAcK
Larrea spp.	Plant	KNApSAcK
Larrea tridentata	Plant	KNApSAcK
Schisandra chinensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Dibenzylbutane lignans

Sub Class

Not Available

Direct Parent

Dibenzylbutane 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

nordihydroguaiaretic acid (CHEBI:73468 )
Lignans (C10719 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	185.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.014 g/L	Not Available
LogP	5.8	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	3.44	ALOGPS
logP	4.76	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	86.62 m³·mol⁻¹	ChemAxon
Polarizability	33.63 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0014325

DrugBank ID

DB00179

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000693

Chemspider ID

64490

KEGG Compound ID

C10719

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Masoprocol

METLIN ID

Not Available

PubChem Compound

71398

PDB ID

Not Available

ChEBI ID

73468

Good Scents ID

Not Available

References

General References

Reed MJ, Meszaros K, Entes LJ, Claypool MD, Pinkett JG, Brignetti D, Luo J, Khandwala A, Reaven GM: Effect of masoprocol on carbohydrate and lipid metabolism in a rat model of Type II diabetes. Diabetologia. 1999 Jan;42(1):102-6. doi: 10.1007/s001250051121. [PubMed:10027587 ]
Gowri MS, Reaven GM, Azhar S: Effect of masoprocol on glucose transport and lipolysis by isolated rat adipocytes. Metabolism. 1999 Apr;48(4):411-4. doi: 10.1016/s0026-0495(99)90096-3. [PubMed:10206430 ]
Gowri MS, Reaven GM, Azhar S: Masoprocol lowers blood pressure in rats with fructose-induced hypertension. Am J Hypertens. 1999 Jul;12(7):744-6. doi: 10.1016/s0895-7061(99)00023-0. [PubMed:10411373 ]
Gowri MS, Azhar RK, Kraemer FB, Reaven GM, Azhar S: Masoprocol decreases rat lipolytic activity by decreasing the phosphorylation of HSL. Am J Physiol Endocrinol Metab. 2000 Sep;279(3):E593-600. doi: 10.1152/ajpendo.2000.279.3.E593. [PubMed:10950827 ]
Scribner KA, Gadbois TM, Gowri M, Azhar S, Reaven GM: Masoprocol decreases serum triglyceride concentrations in rats with fructose-induced hypertriglyceridemia. Metabolism. 2000 Sep;49(9):1106-10. doi: 10.1053/meta.2000.8604. [PubMed:11016888 ]

Showing NP-Card for Masoprocol (NP0000508)

MOL for NP0000508 (Masoprocol)

3D MOL for NP0000508 (Masoprocol)

3D SDF for NP0000508 (Masoprocol)

3D-SDF for NP0000508 (Masoprocol)

PDB for NP0000508 (Masoprocol)

3D PDB for NP0000508 (Masoprocol)

SMILES for NP0000508 (Masoprocol)

INCHI for NP0000508 (Masoprocol)

Structure for NP0000508 (Masoprocol)

3D Structure for NP0000508 (Masoprocol)