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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:04:56 UTC

Update Date

2022-03-07 02:56:15 UTC

HMDB ID

HMDB0039578

Secondary Accession Numbers

HMDB39578

Metabolite Identification

Common Name

1,5-Dihydroxy-2-methoxy-6-methylanthraquinone

Description

1,5-Dihydroxy-2-methoxy-6-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. 1,5-Dihydroxy-2-methoxy-6-methylanthraquinone has been detected, but not quantified in, fruits. This could make 1,5-dihydroxy-2-methoxy-6-methylanthraquinone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1,5-Dihydroxy-2-methoxy-6-methylanthraquinone.

Structure

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

HMDB0039578
     RDKit          3D
1,5-Dihydroxy-2-methoxy-6-methylanthraquinone
 33 35  0  0  0  0  0  0  0  0999 V2000
   -5.7419   -0.9925   -0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5963   -1.1109    0.2921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3339   -0.6843   -0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0987   -0.0808   -1.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8548    0.3515   -1.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7993    0.1724   -0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0352   -0.4316    0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3126   -0.8715    0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4421   -1.4680    2.0742 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0766   -0.6151    1.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0889   -1.1698    2.5137 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4106   -0.1614    1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4652   -0.3433    1.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7101    0.0853    1.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9441    0.6870    0.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2951    1.1457   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8952    0.8864   -0.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2111    1.4898   -1.7774 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6444    0.4530   -0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5368    0.6399   -1.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6815    1.1872   -2.2895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4854   -1.2147   -1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1190    0.0652   -0.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5194   -1.7022   -0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9188    0.0601   -1.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6459    0.8248   -2.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3567   -1.7927    2.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502   -0.8255    2.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5187   -0.0702    2.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5101    2.1637    0.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0328    0.4727    0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4725    1.1167   -1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6938    1.7331   -2.5505 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  2  0
  8  9  1  0
  7 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
  8  3  1  0
 19 12  1  0
 20  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  9 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 18 33  1  0
M  END


  Mrv0541 05061311152D          

 21 23  0  0  0  0            999 V2000
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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    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    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
    4.2868    2.4750    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    0.8250    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
    4.2868    3.3000    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
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
  7  1  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12  9  2  0  0  0  0
 13  7  2  0  0  0  0
 13 11  1  0  0  0  0
 14  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15  8  1  0  0  0  0
 15 12  1  0  0  0  0
 16 10  2  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  2  0  0  0  0
 19 15  2  0  0  0  0
 20 16  1  0  0  0  0
 21  2  1  0  0  0  0
 21 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039578

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c1-7-3-4-8-11(13(7)17)14(18)9-5-6-10(21-2)16(20)12(9)15(8)19/h3-6,17,20H,1-2H3

> <INCHI_KEY>
JJTIQZJKQCQNJK-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.2635

> <EXACT_MASS>
284.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
28.550972041107087

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,5-dihydroxy-2-methoxy-6-methyl-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.97

> <JCHEM_LOGP>
3.9673255549999995

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.211461983316983

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.582067498426218

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5844683449237458

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
76.6172

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,5-dihydroxy-2-methoxy-6-methylanthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039578
     RDKit          3D
1,5-Dihydroxy-2-methoxy-6-methylanthraquinone
 33 35  0  0  0  0  0  0  0  0999 V2000
   -5.7419   -0.9925   -0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5963   -1.1109    0.2921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3339   -0.6843   -0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0987   -0.0808   -1.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8548    0.3515   -1.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7993    0.1724   -0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0352   -0.4316    0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3126   -0.8715    0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4421   -1.4680    2.0742 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0766   -0.6151    1.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0889   -1.1698    2.5137 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4106   -0.1614    1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4652   -0.3433    1.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7101    0.0853    1.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9441    0.6870    0.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2951    1.1457   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8952    0.8864   -0.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2111    1.4898   -1.7774 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6444    0.4530   -0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5368    0.6399   -1.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6815    1.1872   -2.2895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4854   -1.2147   -1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1190    0.0652   -0.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5194   -1.7022   -0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9188    0.0601   -1.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6459    0.8248   -2.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3567   -1.7927    2.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502   -0.8255    2.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5187   -0.0702    2.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5101    2.1637    0.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0328    0.4727    0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4725    1.1167   -1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6938    1.7331   -2.5505 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  2  0
  8  9  1  0
  7 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
  8  3  1  0
 19 12  1  0
 20  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  9 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 18 33  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      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   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       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   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       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   4.620   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       2.667   1.540   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   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2   21                                                            
CONECT    3    4    7                                                       
CONECT    4    3    8                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    1    3   13                                                  
CONECT    8    4   11   15                                                  
CONECT    9    5   12   14                                                  
CONECT   10    6   16   21                                                  
CONECT   11    8   13   14                                                  
CONECT   12    9   15   16                                                  
CONECT   13    7   11   17                                                  
CONECT   14    9   11   18                                                  
CONECT   15    8   12   19                                                  
CONECT   16   10   12   20                                                  
CONECT   17   13                                                            
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21    2   10                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0039578
HETATM    1  C1  UNL     1      -5.742  -0.993  -0.499  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.596  -1.111   0.292  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.334  -0.684  -0.056  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.099  -0.081  -1.268  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.855   0.352  -1.637  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.799   0.172  -0.755  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.035  -0.432   0.458  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.313  -0.871   0.828  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.442  -1.468   2.074  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.077  -0.615   1.376  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.089  -1.170   2.514  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.411  -0.161   1.002  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.465  -0.343   1.890  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.710   0.085   1.529  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.944   0.687   0.320  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.295   1.146  -0.057  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.895   0.886  -0.603  1.00  0.00           C  
HETATM   18  O4  UNL     1       3.211   1.490  -1.777  1.00  0.00           O  
HETATM   19  C15 UNL     1       1.644   0.453  -0.235  1.00  0.00           C  
HETATM   20  C16 UNL     1       0.537   0.640  -1.158  1.00  0.00           C  
HETATM   21  O5  UNL     1       0.681   1.187  -2.290  1.00  0.00           O  
HETATM   22  H1  UNL     1      -5.485  -1.215  -1.571  1.00  0.00           H  
HETATM   23  H2  UNL     1      -6.119   0.065  -0.522  1.00  0.00           H  
HETATM   24  H3  UNL     1      -6.519  -1.702  -0.187  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.919   0.060  -1.957  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.646   0.825  -2.576  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.357  -1.793   2.360  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.250  -0.826   2.846  1.00  0.00           H  
HETATM   29  H8  UNL     1       4.519  -0.070   2.245  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.510   2.164   0.362  1.00  0.00           H  
HETATM   31  H10 UNL     1       6.033   0.473   0.451  1.00  0.00           H  
HETATM   32  H11 UNL     1       5.473   1.117  -1.147  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.694   1.733  -2.550  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   25
CONECT    5    6    6   26
CONECT    6    7   20
CONECT    7    8    8   10
CONECT    8    9
CONECT    9   27
CONECT   10   11   11   12
CONECT   12   13   13   19
CONECT   13   14   28
CONECT   14   15   15   29
CONECT   15   16   17
CONECT   16   30   31   32
CONECT   17   18   19   19
CONECT   18   33
CONECT   19   20
CONECT   20   21   21
END

HMDB0039578
     RDKit          3D
1,5-Dihydroxy-2-methoxy-6-methylanthraquinone
 33 35  0  0  0  0  0  0  0  0999 V2000
   -5.7419   -0.9925   -0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5963   -1.1109    0.2921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3339   -0.6843   -0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0987   -0.0808   -1.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8548    0.3515   -1.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7993    0.1724   -0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0352   -0.4316    0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3126   -0.8715    0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4421   -1.4680    2.0742 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0766   -0.6151    1.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0889   -1.1698    2.5137 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4106   -0.1614    1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4652   -0.3433    1.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7101    0.0853    1.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9441    0.6870    0.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2951    1.1457   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8952    0.8864   -0.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2111    1.4898   -1.7774 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6444    0.4530   -0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5368    0.6399   -1.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6815    1.1872   -2.2895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4854   -1.2147   -1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1190    0.0652   -0.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5194   -1.7022   -0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9188    0.0601   -1.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6459    0.8248   -2.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3567   -1.7927    2.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502   -0.8255    2.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5187   -0.0702    2.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5101    2.1637    0.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0328    0.4727    0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4725    1.1167   -1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6938    1.7331   -2.5505 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  2  0
  8  9  1  0
  7 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
  8  3  1  0
 19 12  1  0
 20  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  9 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 18 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₅

Average Molecular Weight

284.2635

Monoisotopic Molecular Weight

284.068473494

IUPAC Name

1,5-dihydroxy-2-methoxy-6-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

1,5-dihydroxy-2-methoxy-6-methylanthracene-9,10-dione

CAS Registry Number

63965-45-7

SMILES

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

InChI Identifier

InChI=1S/C16H12O5/c1-7-3-4-8-11(13(7)17)14(18)9-5-6-10(21-2)16(20)12(9)15(8)19/h3-6,17,20H,1-2H3

InChI Key

JJTIQZJKQCQNJK-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
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: HMDB0039578)

Cellular substructure

Membrane (HMDB: HMDB0039578)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039578)

Source

Exogenous

Food

Food (HMDB: HMDB0039578)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0039578)

Not Available

Nutrient (HMDB: HMDB0039578)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	252 - 253 °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	0.095 g/L	ALOGPS
logP	2.97	ALOGPS
logP	3.97	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.58	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.62 m³·mol⁻¹	ChemAxon
Polarizability	28.55 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]+	165.56	31661259
DarkChem	[M-H]-	165.972	31661259
DeepCCS	[M+H]+	172.096	30932474
DeepCCS	[M-H]-	169.738	30932474
DeepCCS	[M-2H]-	203.336	30932474
DeepCCS	[M+Na]+	178.563	30932474
AllCCS	[M+H]+	164.0	32859911
AllCCS	[M+H-H2O]+	160.3	32859911
AllCCS	[M+NH4]+	167.4	32859911
AllCCS	[M+Na]+	168.4	32859911
AllCCS	[M-H]-	167.1	32859911
AllCCS	[M+Na-2H]-	166.4	32859911
AllCCS	[M+HCOO]-	165.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,5-Dihydroxy-2-methoxy-6-methylanthraquinone	COC1=C(O)C2=C(C=C1)C(=O)C1=C(C=CC(C)=C1O)C2=O	3923.6	Standard polar	33892256
1,5-Dihydroxy-2-methoxy-6-methylanthraquinone	COC1=C(O)C2=C(C=C1)C(=O)C1=C(C=CC(C)=C1O)C2=O	2588.8	Standard non polar	33892256
1,5-Dihydroxy-2-methoxy-6-methylanthraquinone	COC1=C(O)C2=C(C=C1)C(=O)C1=C(C=CC(C)=C1O)C2=O	2704.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,5-Dihydroxy-2-methoxy-6-methylanthraquinone,1TMS,isomer #1	COC1=CC=C2C(=O)C3=C(O)C(C)=CC=C3C(=O)C2=C1O[Si](C)(C)C	2706.2	Semi standard non polar	33892256
1,5-Dihydroxy-2-methoxy-6-methylanthraquinone,1TMS,isomer #2	COC1=CC=C2C(=O)C3=C(O[Si](C)(C)C)C(C)=CC=C3C(=O)C2=C1O	2748.5	Semi standard non polar	33892256
1,5-Dihydroxy-2-methoxy-6-methylanthraquinone,2TMS,isomer #1	COC1=CC=C2C(=O)C3=C(O[Si](C)(C)C)C(C)=CC=C3C(=O)C2=C1O[Si](C)(C)C	2707.6	Semi standard non polar	33892256
1,5-Dihydroxy-2-methoxy-6-methylanthraquinone,1TBDMS,isomer #1	COC1=CC=C2C(=O)C3=C(O)C(C)=CC=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C	2968.2	Semi standard non polar	33892256
1,5-Dihydroxy-2-methoxy-6-methylanthraquinone,1TBDMS,isomer #2	COC1=CC=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(C)=CC=C3C(=O)C2=C1O	3016.4	Semi standard non polar	33892256
1,5-Dihydroxy-2-methoxy-6-methylanthraquinone,2TBDMS,isomer #1	COC1=CC=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(C)=CC=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C	3214.1	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 - 1,5-Dihydroxy-2-methoxy-6-methylanthraquinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfr-0490000000-89e20d750adcaee4d562	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,5-Dihydroxy-2-methoxy-6-methylanthraquinone GC-MS (2 TMS) - 70eV, Positive	splash10-08mi-7059600000-a376bb4313b7bcafb508	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,5-Dihydroxy-2-methoxy-6-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 - 1,5-Dihydroxy-2-methoxy-6-methylanthraquinone 10V, Positive-QTOF	splash10-000i-0090000000-995ff45d283613b3794b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-2-methoxy-6-methylanthraquinone 20V, Positive-QTOF	splash10-000i-0790000000-442b5e4e461b3eaf2c3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-2-methoxy-6-methylanthraquinone 40V, Positive-QTOF	splash10-0mii-5590000000-02d2ebef4a48cf533a81	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-2-methoxy-6-methylanthraquinone 10V, Negative-QTOF	splash10-001i-0090000000-69f7bd1823f5e39be719	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-2-methoxy-6-methylanthraquinone 20V, Negative-QTOF	splash10-001i-0090000000-7b93d1d3409410c46bbb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-2-methoxy-6-methylanthraquinone 40V, Negative-QTOF	splash10-0a4i-2590000000-4f928f4bc20caf9500fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-2-methoxy-6-methylanthraquinone 10V, Positive-QTOF	splash10-000i-0090000000-edc9ea273e98ea6aa00a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-2-methoxy-6-methylanthraquinone 20V, Positive-QTOF	splash10-000i-0090000000-713acf44f1263827a8c0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-2-methoxy-6-methylanthraquinone 40V, Positive-QTOF	splash10-115i-0690000000-03f8fc5d9568bdfa43ca	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-2-methoxy-6-methylanthraquinone 10V, Negative-QTOF	splash10-001i-0090000000-549f6b30f75977e8ff35	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-2-methoxy-6-methylanthraquinone 20V, Negative-QTOF	splash10-001i-0090000000-0d210f8cb5426a97934f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,5-Dihydroxy-2-methoxy-6-methylanthraquinone 40V, Negative-QTOF	splash10-0a4r-0290000000-6e84630fccd9eb66251a	2021-09-25	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

FDB019200

KNApSAcK ID

Not Available

Chemspider ID

30777354

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13412795

PDB ID

Not Available

ChEBI ID

174711

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 1,5-Dihydroxy-2-methoxy-6-methylanthraquinone (HMDB0039578)

MOL for HMDB0039578 (1,5-Dihydroxy-2-methoxy-6-methylanthraquinone)

3D MOL for HMDB0039578 (1,5-Dihydroxy-2-methoxy-6-methylanthraquinone)

3D SDF for HMDB0039578 (1,5-Dihydroxy-2-methoxy-6-methylanthraquinone)

3D-SDF for HMDB0039578 (1,5-Dihydroxy-2-methoxy-6-methylanthraquinone)

PDB for HMDB0039578 (1,5-Dihydroxy-2-methoxy-6-methylanthraquinone)

3D PDB for HMDB0039578 (1,5-Dihydroxy-2-methoxy-6-methylanthraquinone)

SMILES for HMDB0039578 (1,5-Dihydroxy-2-methoxy-6-methylanthraquinone)

INCHI for HMDB0039578 (1,5-Dihydroxy-2-methoxy-6-methylanthraquinone)

Structure for HMDB0039578 (1,5-Dihydroxy-2-methoxy-6-methylanthraquinone)

3D Structure for HMDB0039578 (1,5-Dihydroxy-2-methoxy-6-methylanthraquinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra