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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:44:38 UTC

Update Date

2022-03-07 02:54:58 UTC

HMDB ID

HMDB0036586

Secondary Accession Numbers

HMDB36586

Metabolite Identification

Common Name

1,3-Dimethoxyanthraquinone

Description

1,3-Dimethoxyanthraquinone belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. 1,3-Dimethoxyanthraquinone has been detected, but not quantified in, several different foods, such as herbs and spices, red tea, black tea, teas (Camellia sinensis), and green tea. This could make 1,3-dimethoxyanthraquinone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1,3-Dimethoxyanthraquinone.

Structure

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

HMDB0036586
     RDKit          3D
1,3-Dimethoxyanthraquinone
 32 34  0  0  0  0  0  0  0  0999 V2000
    4.4093   -1.6591    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9824   -0.3286    0.2117 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6431    0.0184    0.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2447    1.3431    0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9156    1.6638    0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5206    2.9657    0.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3598    4.0812    0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0147    0.6524    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709   -0.6915    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7109   -0.9974    0.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5965   -1.7808    0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2140   -2.9975    0.0865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0138   -1.4422   -0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9248   -2.4766   -0.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2588   -2.1438   -0.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6846   -0.8207   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7463    0.1908   -0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4107   -0.1107   -0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4418    0.9775   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8288    2.1818   -0.0564 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0240   -2.1679    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9644   -2.2047   -0.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5206   -1.6837    0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0470    2.0941    0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3361    3.9089   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6133    4.2869    1.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8995    4.9744   -0.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0209   -2.0503    0.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6569   -3.5239   -0.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0036   -2.9280   -0.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7404   -0.5613   -0.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0472    1.2298   -0.1296 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  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 10  3  1  0
 18 13  1  0
 19  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
 10 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
M  END


  Mrv0541 05061309132D          

 20 22  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
    4.2868    2.4750    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
    0.7145    2.0625    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   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
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  9  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  5  2  0  0  0  0
 11  6  2  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16 11  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  2  0  0  0  0
 18 16  2  0  0  0  0
 19  1  1  0  0  0  0
 19  9  1  0  0  0  0
 20  2  1  0  0  0  0
 20 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036586

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C(OC)=C1)C(=O)C1=CC=CC=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O4/c1-19-9-7-12-14(13(8-9)20-2)16(18)11-6-4-3-5-10(11)15(12)17/h3-8H,1-2H3

> <INCHI_KEY>
ILRJFVJXKPFIAB-UHFFFAOYSA-N

> <FORMULA>
C16H12O4

> <MOLECULAR_WEIGHT>
268.2641

> <EXACT_MASS>
268.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.47892222638891

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-dimethoxy-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
2.603363543333333

> <ALOGPS_LOGS>
-3.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.573603475772579

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
74.0774

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3-dimethoxyanthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036586
     RDKit          3D
1,3-Dimethoxyanthraquinone
 32 34  0  0  0  0  0  0  0  0999 V2000
    4.4093   -1.6591    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9824   -0.3286    0.2117 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6431    0.0184    0.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2447    1.3431    0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9156    1.6638    0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5206    2.9657    0.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3598    4.0812    0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0147    0.6524    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709   -0.6915    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7109   -0.9974    0.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5965   -1.7808    0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2140   -2.9975    0.0865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0138   -1.4422   -0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9248   -2.4766   -0.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2588   -2.1438   -0.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6846   -0.8207   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7463    0.1908   -0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4107   -0.1107   -0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4418    0.9775   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8288    2.1818   -0.0564 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0240   -2.1679    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9644   -2.2047   -0.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5206   -1.6837    0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0470    2.0941    0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3361    3.9089   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6133    4.2869    1.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8995    4.9744   -0.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0209   -2.0503    0.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6569   -3.5239   -0.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0036   -2.9280   -0.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7404   -0.5613   -0.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0472    1.2298   -0.1296 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  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 10  3  1  0
 18 13  1  0
 19  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
 10 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  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   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   3.850   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       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   10                                                       
CONECT    6    4   11                                                       
CONECT    7    9   12                                                       
CONECT    8    9   13                                                       
CONECT    9    7    8   19                                                  
CONECT   10    5   11   15                                                  
CONECT   11    6   10   16                                                  
CONECT   12    7   14   15                                                  
CONECT   13    8   14   20                                                  
CONECT   14   12   13   16                                                  
CONECT   15   10   12   17                                                  
CONECT   16   11   14   18                                                  
CONECT   17   15                                                            
CONECT   18   16                                                            
CONECT   19    1    9                                                       
CONECT   20    2   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0036586
HETATM    1  C1  UNL     1       4.409  -1.659   0.249  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.982  -0.329   0.212  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.643   0.018   0.153  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.245   1.343   0.117  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.916   1.664   0.060  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.521   2.966   0.025  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.360   4.081   0.041  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.015   0.652   0.039  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.371  -0.692   0.074  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.711  -0.997   0.132  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.597  -1.781   0.053  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.214  -2.998   0.087  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.014  -1.442  -0.008  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.925  -2.477  -0.029  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.259  -2.144  -0.086  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.685  -0.821  -0.124  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.746   0.191  -0.102  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.411  -0.111  -0.044  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.442   0.978  -0.023  1.00  0.00           C  
HETATM   20  O4  UNL     1      -1.829   2.182  -0.056  1.00  0.00           O  
HETATM   21  H1  UNL     1       4.024  -2.168   1.164  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.964  -2.205  -0.612  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.521  -1.684   0.226  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.047   2.094   0.138  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.336   3.909  -0.464  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.613   4.287   1.121  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.899   4.974  -0.440  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.021  -2.050   0.160  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.657  -3.524  -0.002  1.00  0.00           H  
HETATM   30  H10 UNL     1      -5.004  -2.928  -0.104  1.00  0.00           H  
HETATM   31  H11 UNL     1      -5.740  -0.561  -0.169  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.047   1.230  -0.130  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   24
CONECT    5    6    8    8
CONECT    6    7
CONECT    7   25   26   27
CONECT    8    9   19
CONECT    9   10   10   11
CONECT   10   28
CONECT   11   12   12   13
CONECT   13   14   14   18
CONECT   14   15   29
CONECT   15   16   16   30
CONECT   16   17   31
CONECT   17   18   18   32
CONECT   18   19
CONECT   19   20   20
END

HMDB0036586
     RDKit          3D
1,3-Dimethoxyanthraquinone
 32 34  0  0  0  0  0  0  0  0999 V2000
    4.4093   -1.6591    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9824   -0.3286    0.2117 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6431    0.0184    0.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2447    1.3431    0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9156    1.6638    0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5206    2.9657    0.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3598    4.0812    0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0147    0.6524    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709   -0.6915    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7109   -0.9974    0.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5965   -1.7808    0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2140   -2.9975    0.0865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0138   -1.4422   -0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9248   -2.4766   -0.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2588   -2.1438   -0.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6846   -0.8207   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7463    0.1908   -0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4107   -0.1107   -0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4418    0.9775   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8288    2.1818   -0.0564 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0240   -2.1679    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9644   -2.2047   -0.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5206   -1.6837    0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0470    2.0941    0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3361    3.9089   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6133    4.2869    1.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8995    4.9744   -0.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0209   -2.0503    0.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6569   -3.5239   -0.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0036   -2.9280   -0.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7404   -0.5613   -0.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0472    1.2298   -0.1296 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  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 10  3  1  0
 18 13  1  0
 19  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
 10 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₄

Average Molecular Weight

268.2641

Monoisotopic Molecular Weight

268.073558872

IUPAC Name

1,3-dimethoxy-9,10-dihydroanthracene-9,10-dione

Traditional Name

1,3-dimethoxyanthracene-9,10-dione

CAS Registry Number

1989-42-0

SMILES

COC1=CC2=C(C(OC)=C1)C(=O)C1=CC=CC=C1C2=O

InChI Identifier

InChI=1S/C16H12O4/c1-19-9-7-12-14(13(8-9)20-2)16(18)11-6-4-3-5-10(11)15(12)17/h3-8H,1-2H3

InChI Key

ILRJFVJXKPFIAB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Anthraquinone
9,10-anthraquinone
Aryl ketone
Anisole
Alkyl aryl ether
Ketone
Ether
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

Membrane (HMDB: HMDB0036586)
Cell membrane (HMDB: HMDB0036586)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036586)

Source

Exogenous

Exogenous (HMDB: HMDB0036586)

Food

Food (HMDB: HMDB0036586)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Beverages (FooDB: FOOD00870)

Endogenous

Plant

Plant (HMDB: HMDB0036586)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0036586)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	154 - 155 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.47 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.03 g/L	ALOGPS
logP	2.65	ALOGPS
logP	2.6	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	74.08 m³·mol⁻¹	ChemAxon
Polarizability	27.48 Å³	ChemAxon
Number of Rings	3	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]+	161.8	31661259
DarkChem	[M-H]-	163.092	31661259
DeepCCS	[M+H]+	161.384	30932474
DeepCCS	[M-H]-	159.026	30932474
DeepCCS	[M-2H]-	191.922	30932474
DeepCCS	[M+Na]+	167.478	30932474
AllCCS	[M+H]+	160.0	32859911
AllCCS	[M+H-H2O]+	156.2	32859911
AllCCS	[M+NH4]+	163.5	32859911
AllCCS	[M+Na]+	164.5	32859911
AllCCS	[M-H]-	164.3	32859911
AllCCS	[M+Na-2H]-	163.6	32859911
AllCCS	[M+HCOO]-	162.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	8.52 minutes	32390414
Predicted by Siyang on May 30, 2022	14.8704 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.42 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2438.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	443.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	184.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	234.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	197.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	617.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	776.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1274.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	465.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1445.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	462.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	454.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	414.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	493.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	61.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,3-Dimethoxyanthraquinone	COC1=CC2=C(C(OC)=C1)C(=O)C1=CC=CC=C1C2=O	3615.9	Standard polar	33892256
1,3-Dimethoxyanthraquinone	COC1=CC2=C(C(OC)=C1)C(=O)C1=CC=CC=C1C2=O	2353.2	Standard non polar	33892256
1,3-Dimethoxyanthraquinone	COC1=CC2=C(C(OC)=C1)C(=O)C1=CC=CC=C1C2=O	2520.3	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 - 1,3-Dimethoxyanthraquinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-03y3-0690000000-ed3cef34a3b3b76b4d7b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,3-Dimethoxyanthraquinone 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 - 1,3-Dimethoxyanthraquinone 10V, Positive-QTOF	splash10-014i-0090000000-078e405d1bb2710413d7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 20V, Positive-QTOF	splash10-014i-0090000000-3987c03cb2dd65eda43e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 40V, Positive-QTOF	splash10-0ka9-5290000000-47bc90fd7782874bcc27	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 10V, Negative-QTOF	splash10-014i-0090000000-b68e39f540bba3e7985a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 20V, Negative-QTOF	splash10-014i-0090000000-4a219a3b225b1c5081b5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 40V, Negative-QTOF	splash10-06ri-1190000000-84b1c6a3ebaf0b74e227	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 10V, Positive-QTOF	splash10-014i-0090000000-30b0502b3411ee2af0fa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 20V, Positive-QTOF	splash10-014i-0090000000-30b0502b3411ee2af0fa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 40V, Positive-QTOF	splash10-0cki-3950000000-da9b7d2f3a4ec5be54f2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 10V, Negative-QTOF	splash10-014i-0090000000-40ddcbafe3b3d6485788	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 20V, Negative-QTOF	splash10-014i-0090000000-40ddcbafe3b3d6485788	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Dimethoxyanthraquinone 40V, Negative-QTOF	splash10-000i-0090000000-c3e0095e2330d6798b59	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB015498

KNApSAcK ID

Not Available

Chemspider ID

320911

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

361511

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1855791

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 1,3-Dimethoxyanthraquinone (HMDB0036586)

MOL for HMDB0036586 (1,3-Dimethoxyanthraquinone)

3D MOL for HMDB0036586 (1,3-Dimethoxyanthraquinone)

3D SDF for HMDB0036586 (1,3-Dimethoxyanthraquinone)

3D-SDF for HMDB0036586 (1,3-Dimethoxyanthraquinone)

PDB for HMDB0036586 (1,3-Dimethoxyanthraquinone)

3D PDB for HMDB0036586 (1,3-Dimethoxyanthraquinone)

SMILES for HMDB0036586 (1,3-Dimethoxyanthraquinone)

INCHI for HMDB0036586 (1,3-Dimethoxyanthraquinone)

Structure for HMDB0036586 (1,3-Dimethoxyanthraquinone)

3D Structure for HMDB0036586 (1,3-Dimethoxyanthraquinone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra