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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:34 UTC

HMDB ID

HMDB0014325

Secondary Accession Numbers

HMDB0012270
HMDB12270
HMDB14325

Metabolite 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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0014325
     RDKit          3D
Masoprocol
 44 45  0  0  0  0  0  0  0  0999 V2000
   -0.7820   -1.5451   -0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6963   -0.1018   -0.2118 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7189    0.3448    0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1009    0.1562    0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7367    1.1542   -0.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0503    1.0145   -0.7587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7448   -0.1589   -0.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0619   -0.2664   -0.9254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1209   -1.1626    0.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7856   -2.3403    0.4986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7981   -0.9964    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173    0.1626    0.2834 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9307    1.6081    0.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6724   -0.1418   -0.8444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0854    0.0584   -0.5479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6353    1.2972   -0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9767    1.5826   -0.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7896    0.6169   -0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1441    0.8359    0.2379 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2473   -0.6298    0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0438   -1.6207    0.7545 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9140   -0.9068   -0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8159   -1.9410   -0.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1265   -2.1891    0.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3789   -1.6494   -1.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8660    0.4910   -1.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5974   -0.1562    1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4917    1.4331    1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2602    2.0981   -0.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5710    1.7880   -1.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6595   -1.0540   -0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7365   -2.5427    0.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3673   -1.8330    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9384   -0.4386    1.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8171    2.3137   -0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167    1.6579    0.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3858    1.8843    1.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5475   -1.2283   -1.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4104    0.4256   -1.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0568    2.1223   -1.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3807    2.5484   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5564    1.7336    0.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6893   -2.5369    0.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5113   -1.8878    0.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
  2 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 11  4  1  0
 22 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  6
  3 27  1  0
  3 28  1  0
  5 29  1  0
  6 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  1
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 21 43  1  0
 22 44  1  0
M  END


  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>
HMDB0014325

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0014325
     RDKit          3D
Masoprocol
 44 45  0  0  0  0  0  0  0  0999 V2000
   -0.7820   -1.5451   -0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6963   -0.1018   -0.2118 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7189    0.3448    0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1009    0.1562    0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7367    1.1542   -0.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0503    1.0145   -0.7587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7448   -0.1589   -0.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0619   -0.2664   -0.9254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1209   -1.1626    0.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7856   -2.3403    0.4986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7981   -0.9964    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173    0.1626    0.2834 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9307    1.6081    0.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6724   -0.1418   -0.8444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0854    0.0584   -0.5479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6353    1.2972   -0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9767    1.5826   -0.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7896    0.6169   -0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1441    0.8359    0.2379 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2473   -0.6298    0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0438   -1.6207    0.7545 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9140   -0.9068   -0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8159   -1.9410   -0.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1265   -2.1891    0.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3789   -1.6494   -1.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8660    0.4910   -1.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5974   -0.1562    1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4917    1.4331    1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2602    2.0981   -0.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5710    1.7880   -1.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6595   -1.0540   -0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7365   -2.5427    0.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3673   -1.8330    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9384   -0.4386    1.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8171    2.3137   -0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167    1.6579    0.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3858    1.8843    1.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5475   -1.2283   -1.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4104    0.4256   -1.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0568    2.1223   -1.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3807    2.5484   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5564    1.7336    0.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6893   -2.5369    0.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5113   -1.8878    0.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
  2 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 11  4  1  0
 22 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  6
  3 27  1  0
  3 28  1  0
  5 29  1  0
  6 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  1
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 21 43  1  0
 22 44  1  0
M  END

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

COMPND    HMDB0014325
HETATM    1  C1  UNL     1      -0.782  -1.545  -0.571  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.696  -0.102  -0.212  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.719   0.345   0.795  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.101   0.156   0.362  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.737   1.154  -0.332  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.050   1.015  -0.759  1.00  0.00           C  
HETATM    7  C7  UNL     1      -5.745  -0.159  -0.482  1.00  0.00           C  
HETATM    8  O1  UNL     1      -7.062  -0.266  -0.925  1.00  0.00           O  
HETATM    9  C8  UNL     1      -5.121  -1.163   0.209  1.00  0.00           C  
HETATM   10  O2  UNL     1      -5.786  -2.340   0.499  1.00  0.00           O  
HETATM   11  C9  UNL     1      -3.798  -0.996   0.627  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.717   0.163   0.283  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.931   1.608   0.683  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.672  -0.142  -0.844  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.085   0.058  -0.548  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.635   1.297  -0.810  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.977   1.583  -0.559  1.00  0.00           C  
HETATM   18  C16 UNL     1       5.790   0.617  -0.037  1.00  0.00           C  
HETATM   19  O3  UNL     1       7.144   0.836   0.238  1.00  0.00           O  
HETATM   20  C17 UNL     1       5.247  -0.630   0.229  1.00  0.00           C  
HETATM   21  O4  UNL     1       6.044  -1.621   0.754  1.00  0.00           O  
HETATM   22  C18 UNL     1       3.914  -0.907  -0.022  1.00  0.00           C  
HETATM   23  H1  UNL     1      -1.816  -1.941  -0.646  1.00  0.00           H  
HETATM   24  H2  UNL     1      -0.126  -2.189   0.053  1.00  0.00           H  
HETATM   25  H3  UNL     1      -0.379  -1.649  -1.623  1.00  0.00           H  
HETATM   26  H4  UNL     1      -0.866   0.491  -1.135  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.597  -0.156   1.782  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.492   1.433   1.003  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.260   2.098  -0.585  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.571   1.788  -1.306  1.00  0.00           H  
HETATM   31  H9  UNL     1      -7.659  -1.054  -0.789  1.00  0.00           H  
HETATM   32  H10 UNL     1      -6.737  -2.543   0.236  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.367  -1.833   1.172  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.938  -0.439   1.190  1.00  0.00           H  
HETATM   35  H13 UNL     1       0.817   2.314  -0.138  1.00  0.00           H  
HETATM   36  H14 UNL     1       2.017   1.658   0.994  1.00  0.00           H  
HETATM   37  H15 UNL     1       0.386   1.884   1.611  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.547  -1.228  -1.128  1.00  0.00           H  
HETATM   39  H17 UNL     1       1.410   0.426  -1.760  1.00  0.00           H  
HETATM   40  H18 UNL     1       3.057   2.122  -1.226  1.00  0.00           H  
HETATM   41  H19 UNL     1       5.381   2.548  -0.770  1.00  0.00           H  
HETATM   42  H20 UNL     1       7.556   1.734   0.052  1.00  0.00           H  
HETATM   43  H21 UNL     1       5.689  -2.537   0.961  1.00  0.00           H  
HETATM   44  H22 UNL     1       3.511  -1.888   0.193  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   12   26
CONECT    3    4   27   28
CONECT    4    5    5   11
CONECT    5    6   29
CONECT    6    7    7   30
CONECT    7    8    9
CONECT    8   31
CONECT    9   10   11   11
CONECT   10   32
CONECT   11   33
CONECT   12   13   14   34
CONECT   13   35   36   37
CONECT   14   15   38   39
CONECT   15   16   16   22
CONECT   16   17   40
CONECT   17   18   18   41
CONECT   18   19   20
CONECT   19   42
CONECT   20   21   22   22
CONECT   21   43
CONECT   22   44
END

HMDB0014325
     RDKit          3D
Masoprocol
 44 45  0  0  0  0  0  0  0  0999 V2000
   -0.7820   -1.5451   -0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6963   -0.1018   -0.2118 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7189    0.3448    0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1009    0.1562    0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7367    1.1542   -0.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0503    1.0145   -0.7587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7448   -0.1589   -0.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0619   -0.2664   -0.9254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1209   -1.1626    0.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7856   -2.3403    0.4986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7981   -0.9964    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173    0.1626    0.2834 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9307    1.6081    0.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6724   -0.1418   -0.8444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0854    0.0584   -0.5479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6353    1.2972   -0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9767    1.5826   -0.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7896    0.6169   -0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1441    0.8359    0.2379 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2473   -0.6298    0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0438   -1.6207    0.7545 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9140   -0.9068   -0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8159   -1.9410   -0.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1265   -2.1891    0.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3789   -1.6494   -1.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8660    0.4910   -1.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5974   -0.1562    1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4917    1.4331    1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2602    2.0981   -0.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5710    1.7880   -1.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6595   -1.0540   -0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7365   -2.5427    0.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3673   -1.8330    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9384   -0.4386    1.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8171    2.3137   -0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167    1.6579    0.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3858    1.8843    1.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5475   -1.2283   -1.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4104    0.4256   -1.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0568    2.1223   -1.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3807    2.5484   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5564    1.7336    0.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6893   -2.5369    0.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5113   -1.8878    0.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
  2 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 11  4  1  0
 22 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  6
  3 27  1  0
  3 28  1  0
  5 29  1  0
  6 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  1
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 21 43  1  0
 22 44  1  0
M  END

View in JSmol View Stereo Labels

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 Molecular Weight

302.3649

Monoisotopic Molecular Weight

302.151809192

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

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 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014325)
Membrane (HMDB: HMDB0014325)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	172.255	31661259
DarkChem	[M-H]-	172.707	31661259
DeepCCS	[M+H]+	179.242	30932474
DeepCCS	[M-H]-	176.884	30932474
DeepCCS	[M-2H]-	210.773	30932474
DeepCCS	[M+Na]+	186.001	30932474
AllCCS	[M+H]+	174.2	32859911
AllCCS	[M+H-H2O]+	170.7	32859911
AllCCS	[M+NH4]+	177.6	32859911
AllCCS	[M+Na]+	178.5	32859911
AllCCS	[M-H]-	176.4	32859911
AllCCS	[M+Na-2H]-	176.3	32859911
AllCCS	[M+HCOO]-	176.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Masoprocol	C[C@@H](CC1=CC(O)=C(O)C=C1)[C@H](C)CC1=CC(O)=C(O)C=C1	4841.8	Standard polar	33892256
Masoprocol	C[C@@H](CC1=CC(O)=C(O)C=C1)[C@H](C)CC1=CC(O)=C(O)C=C1	2890.6	Standard non polar	33892256
Masoprocol	C[C@@H](CC1=CC(O)=C(O)C=C1)[C@H](C)CC1=CC(O)=C(O)C=C1	3023.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Masoprocol,1TMS,isomer #1	C[C@@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)[C@H](C)CC1=CC=C(O)C(O)=C1	2832.1	Semi standard non polar	33892256
Masoprocol,1TMS,isomer #2	C[C@@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)[C@H](C)CC1=CC=C(O)C(O)=C1	2833.6	Semi standard non polar	33892256
Masoprocol,1TMS,isomer #3	C[C@@H](CC1=CC=C(O)C(O)=C1)[C@H](C)CC1=CC=C(O)C(O[Si](C)(C)C)=C1	2832.1	Semi standard non polar	33892256
Masoprocol,1TMS,isomer #4	C[C@@H](CC1=CC=C(O)C(O)=C1)[C@H](C)CC1=CC=C(O[Si](C)(C)C)C(O)=C1	2833.6	Semi standard non polar	33892256
Masoprocol,2TMS,isomer #1	C[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)=C1	2733.2	Semi standard non polar	33892256
Masoprocol,2TMS,isomer #2	C[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)=C1	2719.6	Semi standard non polar	33892256
Masoprocol,2TMS,isomer #3	C[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)=C1	2702.8	Semi standard non polar	33892256
Masoprocol,2TMS,isomer #4	C[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)=C1	2753.6	Semi standard non polar	33892256
Masoprocol,2TMS,isomer #5	C[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)=C1	2719.6	Semi standard non polar	33892256
Masoprocol,2TMS,isomer #6	C[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)=C1	2733.2	Semi standard non polar	33892256
Masoprocol,3TMS,isomer #1	C[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)=C1	2749.6	Semi standard non polar	33892256
Masoprocol,3TMS,isomer #2	C[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)=C1	2740.7	Semi standard non polar	33892256
Masoprocol,3TMS,isomer #3	C[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)=C1	2740.7	Semi standard non polar	33892256
Masoprocol,3TMS,isomer #4	C[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)=C1	2749.6	Semi standard non polar	33892256
Masoprocol,4TMS,isomer #1	C[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)=C1	2792.2	Semi standard non polar	33892256
Masoprocol,1TBDMS,isomer #1	C[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)=C1	3113.7	Semi standard non polar	33892256
Masoprocol,1TBDMS,isomer #2	C[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)=C1	3130.8	Semi standard non polar	33892256
Masoprocol,1TBDMS,isomer #3	C[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)=C1	3113.7	Semi standard non polar	33892256
Masoprocol,1TBDMS,isomer #4	C[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)=C1	3130.8	Semi standard non polar	33892256
Masoprocol,2TBDMS,isomer #1	C[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)=C1	3266.9	Semi standard non polar	33892256
Masoprocol,2TBDMS,isomer #2	C[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)=C1	3286.2	Semi standard non polar	33892256
Masoprocol,2TBDMS,isomer #3	C[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)=C1	3262.5	Semi standard non polar	33892256
Masoprocol,2TBDMS,isomer #4	C[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)=C1	3315.6	Semi standard non polar	33892256
Masoprocol,2TBDMS,isomer #5	C[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)=C1	3286.2	Semi standard non polar	33892256
Masoprocol,2TBDMS,isomer #6	C[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)=C1	3266.9	Semi standard non polar	33892256
Masoprocol,3TBDMS,isomer #1	C[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)=C1	3469.8	Semi standard non polar	33892256
Masoprocol,3TBDMS,isomer #2	C[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)=C1	3441.8	Semi standard non polar	33892256
Masoprocol,3TBDMS,isomer #3	C[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)=C1	3441.8	Semi standard non polar	33892256
Masoprocol,3TBDMS,isomer #4	C[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)=C1	3469.8	Semi standard non polar	33892256
Masoprocol,4TBDMS,isomer #1	C[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)=C1	3623.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Masoprocol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-0900000000-c156a7beced7bc5559ce	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Masoprocol GC-MS (4 TMS) - 70eV, Positive	splash10-004i-1152090000-b4208f8d034e20d028bb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Masoprocol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-0901000000-c0d0caa2c363f17f6c94	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Masoprocol LC-ESI-qTOF , Positive-QTOF	splash10-0uyi-0960000000-911fb528895df2fd3880	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Masoprocol , positive-QTOF	splash10-00di-0911000000-ad449f20d75c55f665cc	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Masoprocol 10V, Positive-QTOF	splash10-0udi-0309000000-b0d493df9d2eda6b0f78	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Masoprocol 20V, Positive-QTOF	splash10-0uk9-0912000000-039497a951e35513d138	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Masoprocol 40V, Positive-QTOF	splash10-0q29-7930000000-54926d894b8847444c11	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Masoprocol 10V, Negative-QTOF	splash10-0udi-0009000000-82abdf1a79106e4c83b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Masoprocol 20V, Negative-QTOF	splash10-0udi-0029000000-098dadf437ef798b4f84	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Masoprocol 40V, Negative-QTOF	splash10-0a4r-0891000000-bf4e7b7c1a5a632b3968	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Masoprocol 10V, Positive-QTOF	splash10-0udi-0219000000-68686370b80d2d5b8f67	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Masoprocol 20V, Positive-QTOF	splash10-00fr-4910000000-8c3f799ce8c8c7964379	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Masoprocol 40V, Positive-QTOF	splash10-00xr-5960000000-56ed4c425972dd72714f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Masoprocol 10V, Negative-QTOF	splash10-0udi-0009000000-65d407b0c8387d27535d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Masoprocol 20V, Negative-QTOF	splash10-0udi-0395000000-159905151a93ed0a844c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Masoprocol 40V, Negative-QTOF	splash10-00xr-3970000000-78d852a0cf5c2bc9adc5	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00179	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00179	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00179

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Arachidonate 5-lipoxygenase

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

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 ]
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 ]
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 ]
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 ]
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 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Cytochrome P450 2J2

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

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 ]

Showing metabocard for Masoprocol (HMDB0014325)

MOL for HMDB0014325 (Masoprocol)

3D MOL for HMDB0014325 (Masoprocol)

3D SDF for HMDB0014325 (Masoprocol)

3D-SDF for HMDB0014325 (Masoprocol)

PDB for HMDB0014325 (Masoprocol)

3D PDB for HMDB0014325 (Masoprocol)

SMILES for HMDB0014325 (Masoprocol)

INCHI for HMDB0014325 (Masoprocol)

Structure for HMDB0014325 (Masoprocol)

3D Structure for HMDB0014325 (Masoprocol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References