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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:58:53 UTC

Update Date

2022-03-07 02:53:38 UTC

HMDB ID

HMDB0033268

Secondary Accession Numbers

HMDB33268

Metabolite Identification

Common Name

1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone

Description

1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. 1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, herbs and spices, pulses, and robusta coffees (Coffea canephora). This could make 1,3,5-trihydroxy-6,7-dimethoxy-2-methylanthraquinone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone.

Structure

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

HMDB0033268
     RDKit          3D
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone
 38 40  0  0  0  0  0  0  0  0999 V2000
   -3.9323   -3.0188    0.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1597   -1.6374    0.7105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0680   -0.7916    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7913   -1.2960    0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035   -0.4437    0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8448    0.9153    0.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259    1.4245    0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3636    2.7505   -0.1326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2098    0.5505    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5086    1.0755    0.2868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2222    1.1296   -0.9349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3215    1.7621   -0.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2311    2.9838   -0.3446 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6848    1.2029   -0.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7921    1.9953   -0.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0605    1.4521   -0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2100    2.2169   -0.5514 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2163    0.0820   -0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625   -0.5605   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0848   -0.6778    0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1756   -2.0588    0.2892 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8055   -0.1535    0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6443   -1.0041    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8105   -2.2504    0.4790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5193   -3.4915   -0.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1510   -3.0679    1.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8050   -3.5399    1.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5836   -2.3410    0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8475    3.5446   -0.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2628    0.8519   -0.7118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7458    0.5005   -1.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2208    2.1900   -1.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825    3.0712   -0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0649    3.2066   -0.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4726   -1.4643   -0.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8123   -0.9287    0.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3454    0.1085   -0.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0884   -2.4950    0.3001 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
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
  6 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
  9  3  1  0
 22 14  1  0
 23  5  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 15 33  1  0
 17 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 21 38  1  0
M  END

  Mrv0541 02241210002D          

 24 26  0  0  0  0            999 V2000
   -0.6596    0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4020    0.6183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4020   -1.0308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421   -0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421    0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004    1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421    1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421    2.6807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004    3.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    0.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4020    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4020    1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    1.8557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    2.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1445   -2.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4020   -1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4020   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004   -1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -2.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6596   -3.0932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1445   -0.6183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1 19  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 20  1  0  0  0  0
  5  6  2  0  0  0  0
  5 12  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 18 24  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 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033268

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C(O)=C1OC)C(=O)C1=C(C(O)=C(C)C(O)=C1)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O7/c1-6-9(18)4-7-11(13(6)19)15(21)8-5-10(23-2)17(24-3)16(22)12(8)14(7)20/h4-5,18-19,22H,1-3H3

> <INCHI_KEY>
RMPPFTPDOBBBQE-UHFFFAOYSA-N

> <FORMULA>
C17H14O7

> <MOLECULAR_WEIGHT>
330.2889

> <EXACT_MASS>
330.073952802

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
32.65512931146834

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3,5-trihydroxy-6,7-dimethoxy-2-methyl-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.32

> <JCHEM_LOGP>
3.5060889676666664

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.849975959294424

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.852661652438938

> <JCHEM_PKA_STRONGEST_BASIC>
-3.348121909411126

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
85.06129999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,5-trihydroxy-6,7-dimethoxy-2-methylanthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033268
     RDKit          3D
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone
 38 40  0  0  0  0  0  0  0  0999 V2000
   -3.9323   -3.0188    0.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1597   -1.6374    0.7105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0680   -0.7916    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7913   -1.2960    0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035   -0.4437    0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8448    0.9153    0.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259    1.4245    0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3636    2.7505   -0.1326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2098    0.5505    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5086    1.0755    0.2868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2222    1.1296   -0.9349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3215    1.7621   -0.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2311    2.9838   -0.3446 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6848    1.2029   -0.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7921    1.9953   -0.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0605    1.4521   -0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2100    2.2169   -0.5514 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2163    0.0820   -0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625   -0.5605   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0848   -0.6778    0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1756   -2.0588    0.2892 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8055   -0.1535    0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6443   -1.0041    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8105   -2.2504    0.4790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5193   -3.4915   -0.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1510   -3.0679    1.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8050   -3.5399    1.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5836   -2.3410    0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8475    3.5446   -0.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2628    0.8519   -0.7118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7458    0.5005   -1.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2208    2.1900   -1.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825    3.0712   -0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0649    3.2066   -0.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4726   -1.4643   -0.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8123   -0.9287    0.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3454    0.1085   -0.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0884   -2.4950    0.3001 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
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
  6 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
  9  3  1  0
 22 14  1  0
 23  5  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 15 33  1  0
 17 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 21 38  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.231   0.384   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.617   1.154   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       2.617  -1.924   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.385  -1.154   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.385   0.384   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.001   1.154   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.001   2.694   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.385   3.464   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.385   5.004   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.001   5.774   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.003   0.384   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.617   1.154   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.617   2.694   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.003   3.464   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.003   5.004   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.003  -4.234   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.617  -3.464   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.617  -1.924   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.385  -1.154   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.001  -1.924   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.001  -3.464   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.385  -4.234   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.231  -5.774   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.003  -1.154   0.000  0.00  0.00           O+0
CONECT    1    2    6   19                                                  
CONECT    2    1                                                            
CONECT    3    4                                                            
CONECT    4    3    5   20                                                  
CONECT    5    4    6   12                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12    5   11   13                                                  
CONECT   13    8   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   17                                                            
CONECT   17   16   18   22                                                  
CONECT   18   17   19   24                                                  
CONECT   19    1   18   20                                                  
CONECT   20    4   19   21                                                  
CONECT   21   20   22                                                       
CONECT   22   17   21   23                                                  
CONECT   23   22                                                            
CONECT   24   18                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0033268
HETATM    1  C1  UNL     1      -3.932  -3.019   0.923  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.160  -1.637   0.711  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.068  -0.792   0.498  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.791  -1.296   0.496  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.703  -0.444   0.283  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.845   0.915   0.068  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.126   1.425   0.070  1.00  0.00           C  
HETATM    8  O2  UNL     1      -2.364   2.750  -0.133  1.00  0.00           O  
HETATM    9  C7  UNL     1      -3.210   0.551   0.286  1.00  0.00           C  
HETATM   10  O3  UNL     1      -4.509   1.076   0.287  1.00  0.00           O  
HETATM   11  C8  UNL     1      -5.222   1.130  -0.935  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.321   1.762  -0.149  1.00  0.00           C  
HETATM   13  O4  UNL     1       0.231   2.984  -0.345  1.00  0.00           O  
HETATM   14  C10 UNL     1       1.685   1.203  -0.148  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.792   1.995  -0.353  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.061   1.452  -0.348  1.00  0.00           C  
HETATM   17  O5  UNL     1       5.210   2.217  -0.551  1.00  0.00           O  
HETATM   18  C13 UNL     1       4.216   0.082  -0.133  1.00  0.00           C  
HETATM   19  C14 UNL     1       5.562  -0.560  -0.117  1.00  0.00           C  
HETATM   20  C15 UNL     1       3.085  -0.678   0.068  1.00  0.00           C  
HETATM   21  O6  UNL     1       3.176  -2.059   0.289  1.00  0.00           O  
HETATM   22  C16 UNL     1       1.806  -0.153   0.067  1.00  0.00           C  
HETATM   23  C17 UNL     1       0.644  -1.004   0.285  1.00  0.00           C  
HETATM   24  O7  UNL     1       0.810  -2.250   0.479  1.00  0.00           O  
HETATM   25  H1  UNL     1      -3.519  -3.492  -0.012  1.00  0.00           H  
HETATM   26  H2  UNL     1      -3.151  -3.068   1.738  1.00  0.00           H  
HETATM   27  H3  UNL     1      -4.805  -3.540   1.316  1.00  0.00           H  
HETATM   28  H4  UNL     1      -1.584  -2.341   0.654  1.00  0.00           H  
HETATM   29  H5  UNL     1      -1.847   3.545  -0.298  1.00  0.00           H  
HETATM   30  H6  UNL     1      -6.263   0.852  -0.712  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.746   0.501  -1.714  1.00  0.00           H  
HETATM   32  H8  UNL     1      -5.221   2.190  -1.264  1.00  0.00           H  
HETATM   33  H9  UNL     1       2.682   3.071  -0.523  1.00  0.00           H  
HETATM   34  H10 UNL     1       5.065   3.207  -0.705  1.00  0.00           H  
HETATM   35  H11 UNL     1       5.473  -1.464  -0.787  1.00  0.00           H  
HETATM   36  H12 UNL     1       5.812  -0.929   0.884  1.00  0.00           H  
HETATM   37  H13 UNL     1       6.345   0.109  -0.473  1.00  0.00           H  
HETATM   38  H14 UNL     1       4.088  -2.495   0.300  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   28
CONECT    5    6    6   23
CONECT    6    7   12
CONECT    7    8    9    9
CONECT    8   29
CONECT    9   10
CONECT   10   11
CONECT   11   30   31   32
CONECT   12   13   13   14
CONECT   14   15   15   22
CONECT   15   16   33
CONECT   16   17   18   18
CONECT   17   34
CONECT   18   19   20
CONECT   19   35   36   37
CONECT   20   21   22   22
CONECT   21   38
CONECT   22   23
CONECT   23   24   24
END

HMDB0033268
     RDKit          3D
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone
 38 40  0  0  0  0  0  0  0  0999 V2000
   -3.9323   -3.0188    0.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1597   -1.6374    0.7105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0680   -0.7916    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7913   -1.2960    0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035   -0.4437    0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8448    0.9153    0.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259    1.4245    0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3636    2.7505   -0.1326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2098    0.5505    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5086    1.0755    0.2868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2222    1.1296   -0.9349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3215    1.7621   -0.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2311    2.9838   -0.3446 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6848    1.2029   -0.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7921    1.9953   -0.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0605    1.4521   -0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2100    2.2169   -0.5514 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2163    0.0820   -0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625   -0.5605   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0848   -0.6778    0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1756   -2.0588    0.2892 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8055   -0.1535    0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6443   -1.0041    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8105   -2.2504    0.4790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5193   -3.4915   -0.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1510   -3.0679    1.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8050   -3.5399    1.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5836   -2.3410    0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8475    3.5446   -0.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2628    0.8519   -0.7118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7458    0.5005   -1.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2208    2.1900   -1.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825    3.0712   -0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0649    3.2066   -0.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4726   -1.4643   -0.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8123   -0.9287    0.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3454    0.1085   -0.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0884   -2.4950    0.3001 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
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
  6 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
  9  3  1  0
 22 14  1  0
 23  5  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 15 33  1  0
 17 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 21 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₁₄O₇

Average Molecular Weight

330.2889

Monoisotopic Molecular Weight

330.073952802

IUPAC Name

1,3,5-trihydroxy-6,7-dimethoxy-2-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

1,3,5-trihydroxy-6,7-dimethoxy-2-methylanthracene-9,10-dione

CAS Registry Number

38934-17-7

SMILES

COC1=CC2=C(C(O)=C1OC)C(=O)C1=C(C(O)=C(C)C(O)=C1)C2=O

InChI Identifier

InChI=1S/C17H14O7/c1-6-9(18)4-7-11(13(6)19)15(21)8-5-10(23-2)17(24-3)16(22)12(8)14(7)20/h4-5,18-19,22H,1-3H3

InChI Key

RMPPFTPDOBBBQE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Aryl ketone
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Vinylogous acid
Ketone
Polyol
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

Extracellular (HMDB: HMDB0033268)
Cytoplasm (HMDB: HMDB0033268)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033268)

Source

Exogenous

Exogenous (HMDB: HMDB0033268)

Food

Food (HMDB: HMDB0033268)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Pulse

Pulses (FooDB: FOOD00867)

Not Available

Nutrient (HMDB: HMDB0033268)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	210 °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	0.14 g/L	ALOGPS
logP	2.32	ALOGPS
logP	3.51	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.85	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	85.06 m³·mol⁻¹	ChemAxon
Polarizability	32.66 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]+	176.698	31661259
DarkChem	[M-H]-	176.314	31661259
DeepCCS	[M+H]+	176.897	30932474
DeepCCS	[M-H]-	174.539	30932474
DeepCCS	[M-2H]-	208.471	30932474
DeepCCS	[M+Na]+	183.699	30932474
AllCCS	[M+H]+	174.2	32859911
AllCCS	[M+H-H2O]+	170.9	32859911
AllCCS	[M+NH4]+	177.2	32859911
AllCCS	[M+Na]+	178.1	32859911
AllCCS	[M-H]-	177.3	32859911
AllCCS	[M+Na-2H]-	176.8	32859911
AllCCS	[M+HCOO]-	176.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone	COC1=CC2=C(C(O)=C1OC)C(=O)C1=C(C(O)=C(C)C(O)=C1)C2=O	4613.5	Standard polar	33892256
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone	COC1=CC2=C(C(O)=C1OC)C(=O)C1=C(C(O)=C(C)C(O)=C1)C2=O	2729.5	Standard non polar	33892256
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone	COC1=CC2=C(C(O)=C1OC)C(=O)C1=C(C(O)=C(C)C(O)=C1)C2=O	3144.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone,1TMS,isomer #1	COC1=CC2=C(C(=O)C3=CC(O)=C(C)C(O)=C3C2=O)C(O[Si](C)(C)C)=C1OC	2944.1	Semi standard non polar	33892256
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone,1TMS,isomer #2	COC1=CC2=C(C(=O)C3=CC(O)=C(C)C(O[Si](C)(C)C)=C3C2=O)C(O)=C1OC	3003.7	Semi standard non polar	33892256
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone,1TMS,isomer #3	COC1=CC2=C(C(=O)C3=CC(O[Si](C)(C)C)=C(C)C(O)=C3C2=O)C(O)=C1OC	3059.7	Semi standard non polar	33892256
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone,2TMS,isomer #1	COC1=CC2=C(C(=O)C3=CC(O[Si](C)(C)C)=C(C)C(O)=C3C2=O)C(O[Si](C)(C)C)=C1OC	2950.5	Semi standard non polar	33892256
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone,2TMS,isomer #2	COC1=CC2=C(C(=O)C3=CC(O)=C(C)C(O[Si](C)(C)C)=C3C2=O)C(O[Si](C)(C)C)=C1OC	2887.6	Semi standard non polar	33892256
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone,2TMS,isomer #3	COC1=CC2=C(C(=O)C3=CC(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)=C3C2=O)C(O)=C1OC	2993.5	Semi standard non polar	33892256
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone,3TMS,isomer #1	COC1=CC2=C(C(=O)C3=CC(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)=C3C2=O)C(O[Si](C)(C)C)=C1OC	2898.4	Semi standard non polar	33892256
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone,1TBDMS,isomer #1	COC1=CC2=C(C(=O)C3=CC(O)=C(C)C(O)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C1OC	3198.3	Semi standard non polar	33892256
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone,1TBDMS,isomer #2	COC1=CC2=C(C(=O)C3=CC(O)=C(C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O)=C1OC	3247.8	Semi standard non polar	33892256
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone,1TBDMS,isomer #3	COC1=CC2=C(C(=O)C3=CC(O[Si](C)(C)C(C)(C)C)=C(C)C(O)=C3C2=O)C(O)=C1OC	3306.6	Semi standard non polar	33892256
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone,2TBDMS,isomer #1	COC1=CC2=C(C(=O)C3=CC(O[Si](C)(C)C(C)(C)C)=C(C)C(O)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C1OC	3452.1	Semi standard non polar	33892256
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone,2TBDMS,isomer #2	COC1=CC2=C(C(=O)C3=CC(O)=C(C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C1OC	3383.3	Semi standard non polar	33892256
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone,2TBDMS,isomer #3	COC1=CC2=C(C(=O)C3=CC(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O)=C1OC	3494.0	Semi standard non polar	33892256
1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone,3TBDMS,isomer #1	COC1=CC2=C(C(=O)C3=CC(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C1OC	3563.4	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 - 1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ue9-0439000000-5109274d173894884c70	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone GC-MS (3 TMS) - 70eV, Positive	splash10-00ai-3160980000-3215c2cec68567b5ea52	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone 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 - 1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone 10V, Positive-QTOF	splash10-001i-0009000000-baccec63fbdaed37bcb9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone 20V, Positive-QTOF	splash10-01q9-0719000000-59e1f3a44e1775b902e4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone 40V, Positive-QTOF	splash10-01q9-1292000000-756e83199aed3bf789e1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone 10V, Negative-QTOF	splash10-004i-0009000000-da0a490f2140cefef480	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone 20V, Negative-QTOF	splash10-01t9-0039000000-65dcf6cd5d7cf9fc752f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone 40V, Negative-QTOF	splash10-0m0x-1191000000-f8d93509da64a4071962	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone 10V, Negative-QTOF	splash10-004i-0009000000-8e9d1a384717180cd0e2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone 20V, Negative-QTOF	splash10-004i-0049000000-5e4ff4e09e6793bc2c15	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone 40V, Negative-QTOF	splash10-0ktf-0090000000-f0900bd537a83c535ac7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone 10V, Positive-QTOF	splash10-001i-0009000000-931b28fcfeb1b8f804fe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone 20V, Positive-QTOF	splash10-001i-0009000000-931b28fcfeb1b8f804fe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone 40V, Positive-QTOF	splash10-0gb9-1793000000-005213b0fed49e56faee	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

FDB011291

KNApSAcK ID

C00058104

Chemspider ID

30776988

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751404

PDB ID

Not Available

ChEBI ID

174452

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 1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone (HMDB0033268)

MOL for HMDB0033268 (1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone)

3D MOL for HMDB0033268 (1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone)

3D SDF for HMDB0033268 (1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone)

3D-SDF for HMDB0033268 (1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone)

PDB for HMDB0033268 (1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone)

3D PDB for HMDB0033268 (1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone)

SMILES for HMDB0033268 (1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone)

INCHI for HMDB0033268 (1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone)

Structure for HMDB0033268 (1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone)

3D Structure for HMDB0033268 (1,3,5-Trihydroxy-6,7-dimethoxy-2-methylanthraquinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra