Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:58:43 UTC

Update Date

2022-03-07 02:53:38 UTC

HMDB ID

HMDB0033265

Secondary Accession Numbers

HMDB33265

Metabolite Identification

Common Name

2-Methoxystypandrone

Description

2-Methoxystypandrone belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). 2-Methoxystypandrone has been detected, but not quantified in, green vegetables. This could make 2-methoxystypandrone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2-Methoxystypandrone.

Structure

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

HMDB0033265
     RDKit          3D
2-Methoxystypandrone
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.9623   -1.4774   -0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5553   -0.1246   -0.1647 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446    0.2803   -0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9627    1.5661   -0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5651    2.0049   -0.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480    3.2250   -0.0368 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4423    1.0588   -0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7673   -0.2813   -0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559   -1.1958   -0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5946   -0.8112   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973   -1.8862   -0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9286    0.5105   -0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2618    1.0180   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5074    0.2791   -0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3898    2.2982   -0.0412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8700    1.4544   -0.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923    2.7621   -0.0355 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1668   -0.6981   -0.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4423   -1.9302   -0.2097 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5915   -2.0599    0.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0752   -1.5460   -0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5705   -1.9004   -1.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7552    2.3121   -0.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0495   -2.2466   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4022   -1.7590   -0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0216   -2.8444   -0.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9459   -2.0660    0.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8385   -0.0568   -1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3366    1.0301    0.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5782   -0.5323    0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7778    3.6165   -0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 12 16  2  0
 16 17  1  0
  8 18  1  0
 18 19  2  0
 18  3  1  0
 16  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 17 31  1  0
M  END


  Mrv0541 05061307012D          

 19 20  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  4  2  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  5  2  0  0  0  0
 11  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15  7  2  0  0  0  0
 16  9  2  0  0  0  0
 17 13  2  0  0  0  0
 18 14  1  0  0  0  0
 19  3  1  0  0  0  0
 19 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033265

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=O)C2=C(C=C(C)C(C(C)=O)=C2O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O5/c1-6-4-8-12(14(18)11(6)7(2)15)9(16)5-10(19-3)13(8)17/h4-5,18H,1-3H3

> <INCHI_KEY>
SSHJHOVVYKCJJI-UHFFFAOYSA-N

> <FORMULA>
C14H12O5

> <MOLECULAR_WEIGHT>
260.2421

> <EXACT_MASS>
260.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
25.81616795961375

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-acetyl-5-hydroxy-2-methoxy-7-methyl-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
2.155991245

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.54999243851384

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.217504701043248

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6840974119799883

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
70.3267

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-acetyl-5-hydroxy-2-methoxy-7-methylnaphthalene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033265
     RDKit          3D
2-Methoxystypandrone
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.9623   -1.4774   -0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5553   -0.1246   -0.1647 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446    0.2803   -0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9627    1.5661   -0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5651    2.0049   -0.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480    3.2250   -0.0368 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4423    1.0588   -0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7673   -0.2813   -0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559   -1.1958   -0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5946   -0.8112   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973   -1.8862   -0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9286    0.5105   -0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2618    1.0180   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5074    0.2791   -0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3898    2.2982   -0.0412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8700    1.4544   -0.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923    2.7621   -0.0355 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1668   -0.6981   -0.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4423   -1.9302   -0.2097 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5915   -2.0599    0.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0752   -1.5460   -0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5705   -1.9004   -1.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7552    2.3121   -0.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0495   -2.2466   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4022   -1.7590   -0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0216   -2.8444   -0.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9459   -2.0660    0.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8385   -0.0568   -1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3366    1.0301    0.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5782   -0.5323    0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7778    3.6165   -0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 12 16  2  0
 16 17  1  0
  8 18  1  0
 18 19  2  0
 18  3  1  0
 16  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 17 31  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3   19                                                            
CONECT    4    6    8                                                       
CONECT    5    9   10                                                       
CONECT    6    1    4   11                                                  
CONECT    7    2   11   15                                                  
CONECT    8    4   12   13                                                  
CONECT    9    5   12   16                                                  
CONECT   10    5   13   19                                                  
CONECT   11    6    7   14                                                  
CONECT   12    8    9   14                                                  
CONECT   13    8   10   17                                                  
CONECT   14   11   12   18                                                  
CONECT   15    7                                                            
CONECT   16    9                                                            
CONECT   17   13                                                            
CONECT   18   14                                                            
CONECT   19    3   10                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0033265
HETATM    1  C1  UNL     1       4.962  -1.477  -0.208  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.555  -0.125  -0.165  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.245   0.280  -0.144  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.963   1.566  -0.100  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.565   2.005  -0.077  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.348   3.225  -0.037  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.442   1.059  -0.101  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.767  -0.281  -0.146  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.256  -1.196  -0.169  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.595  -0.811  -0.149  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.597  -1.886  -0.183  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.929   0.511  -0.104  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.262   1.018  -0.078  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.507   0.279  -0.087  1.00  0.00           C  
HETATM   15  O3  UNL     1      -3.390   2.298  -0.041  1.00  0.00           O  
HETATM   16  C13 UNL     1      -0.870   1.454  -0.080  1.00  0.00           C  
HETATM   17  O4  UNL     1      -1.192   2.762  -0.036  1.00  0.00           O  
HETATM   18  C14 UNL     1       2.167  -0.698  -0.168  1.00  0.00           C  
HETATM   19  O5  UNL     1       2.442  -1.930  -0.210  1.00  0.00           O  
HETATM   20  H1  UNL     1       4.591  -2.060   0.680  1.00  0.00           H  
HETATM   21  H2  UNL     1       6.075  -1.546  -0.190  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.570  -1.900  -1.158  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.755   2.312  -0.081  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.050  -2.247  -0.205  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.402  -1.759  -0.907  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.022  -2.844  -0.475  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.946  -2.066   0.876  1.00  0.00           H  
HETATM   28  H9  UNL     1      -4.838  -0.057  -1.105  1.00  0.00           H  
HETATM   29  H10 UNL     1      -5.337   1.030   0.247  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.578  -0.532   0.653  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.778   3.617  -0.011  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   18
CONECT    4    5   23
CONECT    5    6    6    7
CONECT    7    8    8   16
CONECT    8    9   18
CONECT    9   10   10   24
CONECT   10   11   12
CONECT   11   25   26   27
CONECT   12   13   16   16
CONECT   13   14   15   15
CONECT   14   28   29   30
CONECT   16   17
CONECT   17   31
CONECT   18   19   19
END

HMDB0033265
     RDKit          3D
2-Methoxystypandrone
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.9623   -1.4774   -0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5553   -0.1246   -0.1647 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446    0.2803   -0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9627    1.5661   -0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5651    2.0049   -0.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480    3.2250   -0.0368 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4423    1.0588   -0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7673   -0.2813   -0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559   -1.1958   -0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5946   -0.8112   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973   -1.8862   -0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9286    0.5105   -0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2618    1.0180   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5074    0.2791   -0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3898    2.2982   -0.0412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8700    1.4544   -0.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923    2.7621   -0.0355 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1668   -0.6981   -0.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4423   -1.9302   -0.2097 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5915   -2.0599    0.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0752   -1.5460   -0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5705   -1.9004   -1.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7552    2.3121   -0.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0495   -2.2466   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4022   -1.7590   -0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0216   -2.8444   -0.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9459   -2.0660    0.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8385   -0.0568   -1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3366    1.0301    0.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5782   -0.5323    0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7778    3.6165   -0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 12 16  2  0
 16 17  1  0
  8 18  1  0
 18 19  2  0
 18  3  1  0
 16  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 17 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Methoxy-6-acethyl-7-methyljuglone	HMDB
6-Acetyl-5-hydroxy-2-methoxy-7-methyl-1,4-naphthoquinone	HMDB
2-Methoxystypandrone	MeSH

Chemical Formula

C₁₄H₁₂O₅

Average Molecular Weight

260.2421

Monoisotopic Molecular Weight

260.068473494

IUPAC Name

6-acetyl-5-hydroxy-2-methoxy-7-methyl-1,4-dihydronaphthalene-1,4-dione

Traditional Name

6-acetyl-5-hydroxy-2-methoxy-7-methylnaphthalene-1,4-dione

CAS Registry Number

85122-21-0

SMILES

COC1=CC(=O)C2=C(C=C(C)C(C(C)=O)=C2O)C1=O

InChI Identifier

InChI=1S/C14H12O5/c1-6-4-8-12(14(18)11(6)7(2)15)9(16)5-10(19-3)13(8)17/h4-5,18H,1-3H3

InChI Key

SSHJHOVVYKCJJI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Acetophenone
Aryl alkyl ketone
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
Vinylogous ester
Vinylogous acid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033265)
Cytoplasm (HMDB: HMDB0033265)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033265)

Source

Exogenous

Food

Food (HMDB: HMDB0033265)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0033265)

Not Available

Nutrient (HMDB: HMDB0033265)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	187 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.2 g/L	ALOGPS
logP	2.29	ALOGPS
logP	2.16	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	10.22	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.33 m³·mol⁻¹	ChemAxon
Polarizability	25.82 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]+	160.844	31661259
DarkChem	[M-H]-	160.935	31661259
DeepCCS	[M+H]+	165.925	30932474
DeepCCS	[M-H]-	163.567	30932474
DeepCCS	[M-2H]-	196.453	30932474
DeepCCS	[M+Na]+	172.018	30932474
AllCCS	[M+H]+	157.7	32859911
AllCCS	[M+H-H2O]+	154.0	32859911
AllCCS	[M+NH4]+	161.1	32859911
AllCCS	[M+Na]+	162.1	32859911
AllCCS	[M-H]-	160.9	32859911
AllCCS	[M+Na-2H]-	160.7	32859911
AllCCS	[M+HCOO]-	160.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methoxystypandrone	COC1=CC(=O)C2=C(C=C(C)C(C(C)=O)=C2O)C1=O	3209.6	Standard polar	33892256
2-Methoxystypandrone	COC1=CC(=O)C2=C(C=C(C)C(C(C)=O)=C2O)C1=O	2013.7	Standard non polar	33892256
2-Methoxystypandrone	COC1=CC(=O)C2=C(C=C(C)C(C(C)=O)=C2O)C1=O	2190.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Methoxystypandrone,1TMS,isomer #1	COC1=CC(=O)C2=C(C=C(C)C(C(C)=O)=C2O[Si](C)(C)C)C1=O	2355.1	Semi standard non polar	33892256
2-Methoxystypandrone,1TBDMS,isomer #1	COC1=CC(=O)C2=C(C=C(C)C(C(C)=O)=C2O[Si](C)(C)C(C)(C)C)C1=O	2582.9	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 - 2-Methoxystypandrone GC-MS (Non-derivatized) - 70eV, Positive	splash10-005a-0390000000-5d1c2e57ba01fa9854a1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxystypandrone GC-MS (1 TMS) - 70eV, Positive	splash10-01dr-4396000000-ab5780dead0bd8bf0682	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxystypandrone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxystypandrone 10V, Positive-QTOF	splash10-03di-0090000000-08dcd0160abc32d3a54a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxystypandrone 20V, Positive-QTOF	splash10-03di-0090000000-49104118a10ece7e2068	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxystypandrone 40V, Positive-QTOF	splash10-0006-4390000000-5121a66ed09698b09fd8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxystypandrone 10V, Negative-QTOF	splash10-0a4i-0090000000-9057edbf788e304d2064	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxystypandrone 20V, Negative-QTOF	splash10-0a4i-0090000000-57fe64df837eb0c4bb4f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxystypandrone 40V, Negative-QTOF	splash10-0aor-4490000000-a41915b28ebf4a854694	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxystypandrone 10V, Negative-QTOF	splash10-0a4i-0090000000-3763147f6baebb37818a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxystypandrone 20V, Negative-QTOF	splash10-0a4i-0090000000-341f5c8bbfc5dc5ad774	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxystypandrone 40V, Negative-QTOF	splash10-03dr-0490000000-9a680f66aded2d2e12c0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxystypandrone 10V, Positive-QTOF	splash10-03di-0090000000-e434ca3354d39f88ae1c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxystypandrone 20V, Positive-QTOF	splash10-03dl-0090000000-c126716a21e77435f0cf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxystypandrone 40V, Positive-QTOF	splash10-004i-4790000000-8e5aeaa3f206b3ed806a	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011288

KNApSAcK ID

C00050671

Chemspider ID

139638

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

158739

PDB ID

Not Available

ChEBI ID

Not Available

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2-Methoxystypandrone (HMDB0033265)

MOL for HMDB0033265 (2-Methoxystypandrone)

3D MOL for HMDB0033265 (2-Methoxystypandrone)

3D SDF for HMDB0033265 (2-Methoxystypandrone)

3D-SDF for HMDB0033265 (2-Methoxystypandrone)

PDB for HMDB0033265 (2-Methoxystypandrone)

3D PDB for HMDB0033265 (2-Methoxystypandrone)

SMILES for HMDB0033265 (2-Methoxystypandrone)

INCHI for HMDB0033265 (2-Methoxystypandrone)

Structure for HMDB0033265 (2-Methoxystypandrone)

3D Structure for HMDB0033265 (2-Methoxystypandrone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra