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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:23 UTC

Update Date

2022-03-07 02:53:34 UTC

HMDB ID

HMDB0033036

Secondary Accession Numbers

HMDB33036

Metabolite Identification

Common Name

8-Hydroxy-1-methoxy-3-methylanthraquinone

Description

8-Hydroxy-1-methoxy-3-methylanthraquinone 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. 8-Hydroxy-1-methoxy-3-methylanthraquinone has been detected, but not quantified in, garden rhubarbs (Rheum rhabarbarum) and green vegetables. This could make 8-hydroxy-1-methoxy-3-methylanthraquinone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 8-Hydroxy-1-methoxy-3-methylanthraquinone.

Structure

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

HMDB0033036
     RDKit          3D
8-Hydroxy-1-methoxy-3-methylanthraquinone
 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.9808    2.8273   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7287    2.1908    0.0302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6025    0.7938    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7187   -0.0108   -0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937   -1.3917   -0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8181   -2.2315   -0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -1.9181   -0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1970   -1.1395    0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3480    0.2214    0.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8295    1.1017    0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6401    2.3437    0.1403 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1569    0.4823    0.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2745    1.3039    0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2254    2.6626    0.2643 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5187    0.6481    0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6311   -0.7030    0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5205   -1.5121    0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2764   -0.9098    0.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1115   -1.7769    0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2231   -3.0478    0.0329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3680    2.9214   -1.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7497    2.3307    0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8231    3.8909    0.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7186    0.4198   -0.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5061   -1.8895   -0.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4030   -2.2033    0.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4800   -3.2796   -0.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2139   -3.0008   -0.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5189    3.3115    0.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3869    1.3225    0.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259   -1.1716    0.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6325   -2.5864    0.1525 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  9  3  1  0
 18 12  1  0
 19  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
M  END


  Mrv0541 05061306522D          

 20 22  0  0  0  0            999 V2000
    0.0000    0.8250    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
    4.2868    0.8250    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
    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
    2.1434    1.2375    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    2.4750    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    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
    4.2868    3.3000    0.0000 O   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
    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
  8  1  1  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  5  2  0  0  0  0
 12  7  2  0  0  0  0
 13  9  2  0  0  0  0
 13 11  1  0  0  0  0
 14 10  2  0  0  0  0
 14 12  1  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 11  1  0  0  0  0
 18 15  2  0  0  0  0
 19 16  2  0  0  0  0
 20  2  1  0  0  0  0
 20 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033036

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(C)=CC2=C1C(=O)C1=C(C=CC=C1O)C2=O

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

> <INCHI_KEY>
KVRUANCWPQJDMF-UHFFFAOYSA-N

> <FORMULA>
C16H12O4

> <MOLECULAR_WEIGHT>
268.2641

> <EXACT_MASS>
268.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.49639227364858

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-1-methoxy-3-methyl-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
3.33

> <JCHEM_LOGP>
3.620890876666666

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.393212481488305

> <JCHEM_PKA_STRONGEST_BASIC>
-4.446780263003414

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
74.63629999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033036
     RDKit          3D
8-Hydroxy-1-methoxy-3-methylanthraquinone
 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.9808    2.8273   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7287    2.1908    0.0302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6025    0.7938    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7187   -0.0108   -0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937   -1.3917   -0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8181   -2.2315   -0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -1.9181   -0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1970   -1.1395    0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3480    0.2214    0.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8295    1.1017    0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6401    2.3437    0.1403 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1569    0.4823    0.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2745    1.3039    0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2254    2.6626    0.2643 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5187    0.6481    0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6311   -0.7030    0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5205   -1.5121    0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2764   -0.9098    0.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1115   -1.7769    0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2231   -3.0478    0.0329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3680    2.9214   -1.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7497    2.3307    0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8231    3.8909    0.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7186    0.4198   -0.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5061   -1.8895   -0.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4030   -2.2033    0.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4800   -3.2796   -0.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2139   -3.0008   -0.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5189    3.3115    0.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3869    1.3225    0.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259   -1.1716    0.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6325   -2.5864    0.1525 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  9  3  1  0
 18 12  1  0
 19  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  7 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       0.000   1.540   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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   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       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   3.850   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       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   6.160   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    8                                                            
CONECT    2   20                                                            
CONECT    3    4    5                                                       
CONECT    4    3    9                                                       
CONECT    5    3   11                                                       
CONECT    6    8   10                                                       
CONECT    7    8   12                                                       
CONECT    8    1    6    7                                                  
CONECT    9    4   13   15                                                  
CONECT   10    6   14   15                                                  
CONECT   11    5   13   17                                                  
CONECT   12    7   14   20                                                  
CONECT   13    9   11   16                                                  
CONECT   14   10   12   16                                                  
CONECT   15    9   10   18                                                  
CONECT   16   13   14   19                                                  
CONECT   17   11                                                            
CONECT   18   15                                                            
CONECT   19   16                                                            
CONECT   20    2   12                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0033036
HETATM    1  C1  UNL     1      -2.981   2.827  -0.010  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.729   2.191   0.030  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.603   0.794   0.001  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.719  -0.011  -0.069  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.594  -1.392  -0.097  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.818  -2.232  -0.173  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.322  -1.918  -0.053  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.197  -1.140   0.016  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.348   0.221   0.043  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.830   1.102   0.118  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.640   2.344   0.140  1.00  0.00           O  
HETATM   12  C10 UNL     1       2.157   0.482   0.162  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.275   1.304   0.233  1.00  0.00           C  
HETATM   14  O3  UNL     1       3.225   2.663   0.264  1.00  0.00           O  
HETATM   15  C12 UNL     1       4.519   0.648   0.272  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.631  -0.703   0.244  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.521  -1.512   0.174  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.276  -0.910   0.133  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.111  -1.777   0.059  1.00  0.00           C  
HETATM   20  O4  UNL     1       1.223  -3.048   0.033  1.00  0.00           O  
HETATM   21  H1  UNL     1      -3.368   2.921  -1.055  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.750   2.331   0.610  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.823   3.891   0.333  1.00  0.00           H  
HETATM   24  H4  UNL     1      -3.719   0.420  -0.103  1.00  0.00           H  
HETATM   25  H5  UNL     1      -4.506  -1.890  -0.969  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.403  -2.203   0.777  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.480  -3.280  -0.329  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.214  -3.001  -0.075  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.519   3.312   0.249  1.00  0.00           H  
HETATM   30  H10 UNL     1       5.387   1.322   0.328  1.00  0.00           H  
HETATM   31  H11 UNL     1       5.626  -1.172   0.277  1.00  0.00           H  
HETATM   32  H12 UNL     1       3.633  -2.586   0.152  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   24
CONECT    5    6    7    7
CONECT    6   25   26   27
CONECT    7    8   28
CONECT    8    9    9   19
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   13   18
CONECT   13   14   15
CONECT   14   29
CONECT   15   16   16   30
CONECT   16   17   31
CONECT   17   18   18   32
CONECT   18   19
CONECT   19   20   20
END

HMDB0033036
     RDKit          3D
8-Hydroxy-1-methoxy-3-methylanthraquinone
 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.9808    2.8273   -0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7287    2.1908    0.0302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6025    0.7938    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7187   -0.0108   -0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937   -1.3917   -0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8181   -2.2315   -0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -1.9181   -0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1970   -1.1395    0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3480    0.2214    0.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8295    1.1017    0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6401    2.3437    0.1403 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1569    0.4823    0.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2745    1.3039    0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2254    2.6626    0.2643 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5187    0.6481    0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6311   -0.7030    0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5205   -1.5121    0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2764   -0.9098    0.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1115   -1.7769    0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2231   -3.0478    0.0329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3680    2.9214   -1.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7497    2.3307    0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8231    3.8909    0.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7186    0.4198   -0.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5061   -1.8895   -0.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4030   -2.2033    0.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4800   -3.2796   -0.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2139   -3.0008   -0.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5189    3.3115    0.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3869    1.3225    0.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259   -1.1716    0.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6325   -2.5864    0.1525 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  9  3  1  0
 18 12  1  0
 19  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  7 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

8-hydroxy-1-methoxy-3-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione

CAS Registry Number

67116-22-7

SMILES

COC1=CC(C)=CC2=C1C(=O)C1=C(C=CC=C1O)C2=O

InChI Identifier

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

InChI Key

KVRUANCWPQJDMF-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
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Vinylogous acid
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

Cell membrane (HMDB: HMDB0033036)

Cellular substructure

Membrane (HMDB: HMDB0033036)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033036)

Source

Exogenous

Food

Food (HMDB: HMDB0033036)

Vegetable

Stalk vegetable

Garden rhubarb (FooDB: FOOD00154)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0033036)

Not Available

Nutrient (HMDB: HMDB0033036)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	199 - 200 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.25 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	0.04 g/L	ALOGPS
logP	3.33	ALOGPS
logP	3.62	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.39	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.64 m³·mol⁻¹	ChemAxon
Polarizability	27.5 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]+	162.068	31661259
DarkChem	[M-H]-	160.356	31661259
DeepCCS	[M+H]+	165.236	30932474
DeepCCS	[M-H]-	162.878	30932474
DeepCCS	[M-2H]-	195.764	30932474
DeepCCS	[M+Na]+	171.33	30932474
AllCCS	[M+H]+	159.4	32859911
AllCCS	[M+H-H2O]+	155.6	32859911
AllCCS	[M+NH4]+	163.0	32859911
AllCCS	[M+Na]+	164.0	32859911
AllCCS	[M-H]-	163.5	32859911
AllCCS	[M+Na-2H]-	162.7	32859911
AllCCS	[M+HCOO]-	162.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxy-1-methoxy-3-methylanthraquinone	COC1=CC(C)=CC2=C1C(=O)C1=C(C=CC=C1O)C2=O	3554.7	Standard polar	33892256
8-Hydroxy-1-methoxy-3-methylanthraquinone	COC1=CC(C)=CC2=C1C(=O)C1=C(C=CC=C1O)C2=O	2404.0	Standard non polar	33892256
8-Hydroxy-1-methoxy-3-methylanthraquinone	COC1=CC(C)=CC2=C1C(=O)C1=C(C=CC=C1O)C2=O	2464.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxy-1-methoxy-3-methylanthraquinone,1TMS,isomer #1	COC1=CC(C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1C2=O	2526.0	Semi standard non polar	33892256
8-Hydroxy-1-methoxy-3-methylanthraquinone,1TBDMS,isomer #1	COC1=CC(C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1C2=O	2781.3	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 - 8-Hydroxy-1-methoxy-3-methylanthraquinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6w-0790000000-947f35eb824753261993	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxy-1-methoxy-3-methylanthraquinone GC-MS (1 TMS) - 70eV, Positive	splash10-006t-5965000000-a2f10643a8013f36316f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxy-1-methoxy-3-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 - 8-Hydroxy-1-methoxy-3-methylanthraquinone 10V, Positive-QTOF	splash10-014i-0090000000-ae5ae83fd3e1c1a9d78f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-1-methoxy-3-methylanthraquinone 20V, Positive-QTOF	splash10-014i-0090000000-1f32408e7cef5b7a59c2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-1-methoxy-3-methylanthraquinone 40V, Positive-QTOF	splash10-01bl-9550000000-080bb09d0cbb81c1c296	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-1-methoxy-3-methylanthraquinone 10V, Negative-QTOF	splash10-014i-0090000000-c22861275d0e63aa3cc5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-1-methoxy-3-methylanthraquinone 20V, Negative-QTOF	splash10-014i-0090000000-6ce2a424b125457cd715	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-1-methoxy-3-methylanthraquinone 40V, Negative-QTOF	splash10-00kr-8590000000-ef9ea03f18f7e1a659b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-1-methoxy-3-methylanthraquinone 10V, Negative-QTOF	splash10-014i-0090000000-40ddcbafe3b3d6485788	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-1-methoxy-3-methylanthraquinone 20V, Negative-QTOF	splash10-014i-0090000000-40ddcbafe3b3d6485788	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-1-methoxy-3-methylanthraquinone 40V, Negative-QTOF	splash10-052r-0090000000-38e4fa4a2dbaf458f202	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-1-methoxy-3-methylanthraquinone 10V, Positive-QTOF	splash10-014i-0090000000-30b0502b3411ee2af0fa	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-1-methoxy-3-methylanthraquinone 20V, Positive-QTOF	splash10-014i-0090000000-a2e01996ec628a92e253	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-1-methoxy-3-methylanthraquinone 40V, Positive-QTOF	splash10-00di-1970000000-e1ab9d7b34037ca19226	2021-09-23	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

FDB011028

KNApSAcK ID

Not Available

Chemspider ID

10408856

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13412789

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1833051

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 8-Hydroxy-1-methoxy-3-methylanthraquinone (HMDB0033036)

MOL for HMDB0033036 (8-Hydroxy-1-methoxy-3-methylanthraquinone)

3D MOL for HMDB0033036 (8-Hydroxy-1-methoxy-3-methylanthraquinone)

3D SDF for HMDB0033036 (8-Hydroxy-1-methoxy-3-methylanthraquinone)

3D-SDF for HMDB0033036 (8-Hydroxy-1-methoxy-3-methylanthraquinone)

PDB for HMDB0033036 (8-Hydroxy-1-methoxy-3-methylanthraquinone)

3D PDB for HMDB0033036 (8-Hydroxy-1-methoxy-3-methylanthraquinone)

SMILES for HMDB0033036 (8-Hydroxy-1-methoxy-3-methylanthraquinone)

INCHI for HMDB0033036 (8-Hydroxy-1-methoxy-3-methylanthraquinone)

Structure for HMDB0033036 (8-Hydroxy-1-methoxy-3-methylanthraquinone)

3D Structure for HMDB0033036 (8-Hydroxy-1-methoxy-3-methylanthraquinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra