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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:17:17 UTC

Update Date

2022-03-07 02:54:06 UTC

HMDB ID

HMDB0034443

Secondary Accession Numbers

HMDB34443

Metabolite Identification

Common Name

Questinol

Description

Questinol 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. Questinol has been detected, but not quantified in, green vegetables. This could make questinol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Questinol.

Structure

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

HMDB0034443
     RDKit          3D
Questinol
 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.2862   -2.2172    1.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0191   -1.7187    0.7972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7412   -0.4721    0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7514    0.4196    0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4892    1.6945   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5180    2.6063   -0.6824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1692    2.0320   -0.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1413    1.1718   -0.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4476   -0.0947    0.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3239   -0.9908    0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5176   -2.1518    0.7429 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0602   -0.5990    0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0762   -1.5099    0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7737   -2.7892    0.7827 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3754   -1.1319    0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700    0.1203   -0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0916    0.4950   -0.7246 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6632    1.0750    0.4180 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6642    1.0261   -0.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3611    0.6587   -0.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2366    1.5643   -0.7043 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5220    2.7083   -1.1544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7351   -2.8301    0.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0233   -1.4574    1.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1730   -2.9024    1.9748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8011    0.2024    0.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7861    3.2264    0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9155    3.0255   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5319   -3.4156    0.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1590   -1.8640    0.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6709   -0.4554   -0.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1511    1.1536   -1.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9761    1.4048    1.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8556    2.0155   -1.0976 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  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  9  3  1  0
 20 12  1  0
 21  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
M  END


  Mrv0541 05061307492D          

 22 24  0  0  0  0            999 V2000
    0.7145    3.7125    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
    5.7158    0.8250    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
    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
    6.4302    1.2375    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
    4.2868    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
  7  2  2  0  0  0  0
  7  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  2  1  0  0  0  0
 10  4  1  0  0  0  0
 11  3  2  0  0  0  0
 12  5  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  6  1  0  0  0  0
 18  8  1  0  0  0  0
 19 11  1  0  0  0  0
 20 15  2  0  0  0  0
 21 16  2  0  0  0  0
 22  1  1  0  0  0  0
 22 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034443

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-22-12-5-8(18)4-10-14(12)16(21)13-9(15(10)20)2-7(6-17)3-11(13)19/h2-5,17-19H,6H2,1H3

> <INCHI_KEY>
SNBGJGNOQURXCI-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.2629

> <EXACT_MASS>
300.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.60127538262616

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,6-dihydroxy-3-(hydroxymethyl)-8-methoxy-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
2.036554398333333

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.28470117036344

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.318810557321309

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9453240586977527

> <JCHEM_POLAR_SURFACE_AREA>
104.05999999999999

> <JCHEM_REFRACTIVITY>
78.39189999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,6-dihydroxy-3-(hydroxymethyl)-8-methoxyanthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034443
     RDKit          3D
Questinol
 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.2862   -2.2172    1.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0191   -1.7187    0.7972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7412   -0.4721    0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7514    0.4196    0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4892    1.6945   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5180    2.6063   -0.6824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1692    2.0320   -0.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1413    1.1718   -0.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4476   -0.0947    0.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3239   -0.9908    0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5176   -2.1518    0.7429 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0602   -0.5990    0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0762   -1.5099    0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7737   -2.7892    0.7827 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3754   -1.1319    0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700    0.1203   -0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0916    0.4950   -0.7246 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6632    1.0750    0.4180 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6642    1.0261   -0.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3611    0.6587   -0.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2366    1.5643   -0.7043 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5220    2.7083   -1.1544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7351   -2.8301    0.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0233   -1.4574    1.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1730   -2.9024    1.9748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8011    0.2024    0.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7861    3.2264    0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9155    3.0255   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5319   -3.4156    0.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1590   -1.8640    0.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6709   -0.4554   -0.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1511    1.1536   -1.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9761    1.4048    1.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8556    2.0155   -1.0976 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  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  9  3  1  0
 20 12  1  0
 21  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   2.310   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      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2    7    9                                                       
CONECT    3    7   11                                                       
CONECT    4    8   10                                                       
CONECT    5    8   12                                                       
CONECT    6    7   17                                                       
CONECT    7    2    3    6                                                  
CONECT    8    4    5   18                                                  
CONECT    9    2   13   15                                                  
CONECT   10    4   14   15                                                  
CONECT   11    3   13   19                                                  
CONECT   12    5   14   22                                                  
CONECT   13    9   11   16                                                  
CONECT   14   10   12   16                                                  
CONECT   15    9   10   20                                                  
CONECT   16   13   14   21                                                  
CONECT   17    6                                                            
CONECT   18    8                                                            
CONECT   19   11                                                            
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22    1   12                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0034443
HETATM    1  C1  UNL     1      -4.286  -2.217   1.092  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.019  -1.719   0.797  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.741  -0.472   0.310  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.751   0.420   0.065  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.489   1.695  -0.432  1.00  0.00           C  
HETATM    6  O2  UNL     1      -4.518   2.606  -0.682  1.00  0.00           O  
HETATM    7  C5  UNL     1      -2.169   2.032  -0.671  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.141   1.172  -0.440  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.448  -0.095   0.058  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.324  -0.991   0.294  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.518  -2.152   0.743  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.060  -0.599   0.029  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.076  -1.510   0.281  1.00  0.00           C  
HETATM   14  O4  UNL     1       1.774  -2.789   0.783  1.00  0.00           O  
HETATM   15  C11 UNL     1       3.375  -1.132   0.028  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.670   0.120  -0.463  1.00  0.00           C  
HETATM   17  C13 UNL     1       5.092   0.495  -0.725  1.00  0.00           C  
HETATM   18  O5  UNL     1       5.663   1.075   0.418  1.00  0.00           O  
HETATM   19  C14 UNL     1       2.664   1.026  -0.713  1.00  0.00           C  
HETATM   20  C15 UNL     1       1.361   0.659  -0.464  1.00  0.00           C  
HETATM   21  C16 UNL     1       0.237   1.564  -0.704  1.00  0.00           C  
HETATM   22  O6  UNL     1       0.522   2.708  -1.154  1.00  0.00           O  
HETATM   23  H1  UNL     1      -4.735  -2.830   0.286  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.023  -1.457   1.401  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.173  -2.902   1.975  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.801   0.202   0.236  1.00  0.00           H  
HETATM   27  H5  UNL     1      -4.786   3.226   0.088  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.915   3.025  -1.062  1.00  0.00           H  
HETATM   29  H7  UNL     1       2.532  -3.416   0.950  1.00  0.00           H  
HETATM   30  H8  UNL     1       4.159  -1.864   0.233  1.00  0.00           H  
HETATM   31  H9  UNL     1       5.671  -0.455  -0.912  1.00  0.00           H  
HETATM   32  H10 UNL     1       5.151   1.154  -1.593  1.00  0.00           H  
HETATM   33  H11 UNL     1       4.976   1.405   1.045  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.856   2.016  -1.098  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   26
CONECT    5    6    7    7
CONECT    6   27
CONECT    7    8   28
CONECT    8    9    9   21
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   13   20
CONECT   13   14   15
CONECT   14   29
CONECT   15   16   16   30
CONECT   16   17   19
CONECT   17   18   31   32
CONECT   18   33
CONECT   19   20   20   34
CONECT   20   21
CONECT   21   22   22
END

HMDB0034443
     RDKit          3D
Questinol
 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.2862   -2.2172    1.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0191   -1.7187    0.7972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7412   -0.4721    0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7514    0.4196    0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4892    1.6945   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5180    2.6063   -0.6824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1692    2.0320   -0.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1413    1.1718   -0.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4476   -0.0947    0.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3239   -0.9908    0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5176   -2.1518    0.7429 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0602   -0.5990    0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0762   -1.5099    0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7737   -2.7892    0.7827 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3754   -1.1319    0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700    0.1203   -0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0916    0.4950   -0.7246 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6632    1.0750    0.4180 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6642    1.0261   -0.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3611    0.6587   -0.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2366    1.5643   -0.7043 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5220    2.7083   -1.1544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7351   -2.8301    0.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0233   -1.4574    1.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1730   -2.9024    1.9748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8011    0.2024    0.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7861    3.2264    0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9155    3.0255   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5319   -3.4156    0.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1590   -1.8640    0.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6709   -0.4554   -0.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1511    1.1536   -1.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9761    1.4048    1.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8556    2.0155   -1.0976 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  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  9  3  1  0
 20 12  1  0
 21  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,6-Dihydroxy-3-(hydroxymethyl)-8-methoxy-9,10-anthracenedione	Kegg
1,6-Dihydroxy-3-hydroxymethyl-8-methoxyanthraquinone	HMDB

Chemical Formula

C₁₆H₁₂O₆

Average Molecular Weight

300.2629

Monoisotopic Molecular Weight

300.063388116

IUPAC Name

1,6-dihydroxy-3-(hydroxymethyl)-8-methoxy-9,10-dihydroanthracene-9,10-dione

Traditional Name

1,6-dihydroxy-3-(hydroxymethyl)-8-methoxyanthracene-9,10-dione

CAS Registry Number

35688-09-6

SMILES

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

InChI Identifier

InChI=1S/C16H12O6/c1-22-12-5-8(18)4-10-14(12)16(21)13-9(15(10)20)2-7(6-17)3-11(13)19/h2-5,17-19H,6H2,1H3

InChI Key

SNBGJGNOQURXCI-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
Anisole
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Vinylogous acid
Ketone
Ether
Alcohol
Organooxygen compound
Primary alcohol
Aromatic alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

hydroxyanthraquinones (CHEBI:81349 )
Anthraquinone type (C17811 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034443)
Cytoplasm (HMDB: HMDB0034443)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034443)

Source

Exogenous

Exogenous (HMDB: HMDB0034443)

Food

Food (HMDB: HMDB0034443)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0034443)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034443)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	280 - 282 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	120.9 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	0.19 g/L	ALOGPS
logP	2.34	ALOGPS
logP	2.04	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	7.32	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.39 m³·mol⁻¹	ChemAxon
Polarizability	29.6 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]+	170.428	31661259
DarkChem	[M-H]-	169.328	31661259
DeepCCS	[M+H]+	171.233	30932474
DeepCCS	[M-H]-	168.875	30932474
DeepCCS	[M-2H]-	202.376	30932474
DeepCCS	[M+Na]+	177.603	30932474
AllCCS	[M+H]+	167.6	32859911
AllCCS	[M+H-H2O]+	164.1	32859911
AllCCS	[M+NH4]+	170.8	32859911
AllCCS	[M+Na]+	171.8	32859911
AllCCS	[M-H]-	169.5	32859911
AllCCS	[M+Na-2H]-	169.0	32859911
AllCCS	[M+HCOO]-	168.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.16 minutes	32390414
Predicted by Siyang on May 30, 2022	11.2144 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.51 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2142.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	257.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	121.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	108.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	481.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	538.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	114.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	839.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	348.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1407.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	353.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	361.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	361.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	235.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	185.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Questinol	COC1=CC(O)=CC2=C1C(=O)C1=C(C=C(CO)C=C1O)C2=O	4359.5	Standard polar	33892256
Questinol	COC1=CC(O)=CC2=C1C(=O)C1=C(C=C(CO)C=C1O)C2=O	2721.9	Standard non polar	33892256
Questinol	COC1=CC(O)=CC2=C1C(=O)C1=C(C=C(CO)C=C1O)C2=O	3123.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Questinol,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(CO)C=C1C2=O	2853.8	Semi standard non polar	33892256
Questinol,1TMS,isomer #2	COC1=CC(O)=CC2=C1C(=O)C1=C(O)C=C(CO[Si](C)(C)C)C=C1C2=O	2827.0	Semi standard non polar	33892256
Questinol,1TMS,isomer #3	COC1=CC(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(CO)C=C1C2=O	2825.5	Semi standard non polar	33892256
Questinol,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(CO)C=C1C2=O	2820.1	Semi standard non polar	33892256
Questinol,2TMS,isomer #2	COC1=CC(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(CO[Si](C)(C)C)C=C1C2=O	2833.3	Semi standard non polar	33892256
Questinol,2TMS,isomer #3	COC1=CC(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(CO[Si](C)(C)C)C=C1C2=O	2827.6	Semi standard non polar	33892256
Questinol,3TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(CO[Si](C)(C)C)C=C1C2=O	2837.5	Semi standard non polar	33892256
Questinol,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(CO)C=C1C2=O	3091.0	Semi standard non polar	33892256
Questinol,1TBDMS,isomer #2	COC1=CC(O)=CC2=C1C(=O)C1=C(O)C=C(CO[Si](C)(C)C(C)(C)C)C=C1C2=O	3063.6	Semi standard non polar	33892256
Questinol,1TBDMS,isomer #3	COC1=CC(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(CO)C=C1C2=O	3078.1	Semi standard non polar	33892256
Questinol,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(CO)C=C1C2=O	3294.4	Semi standard non polar	33892256
Questinol,2TBDMS,isomer #2	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O)C=C(CO[Si](C)(C)C(C)(C)C)C=C1C2=O	3293.7	Semi standard non polar	33892256
Questinol,2TBDMS,isomer #3	COC1=CC(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(CO[Si](C)(C)C(C)(C)C)C=C1C2=O	3289.4	Semi standard non polar	33892256
Questinol,3TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(CO[Si](C)(C)C(C)(C)C)C=C1C2=O	3480.0	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 - Questinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-0490000000-270d50358cb5e93b1eea	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Questinol GC-MS (3 TMS) - 70eV, Positive	splash10-0uk9-3280890000-5414878b5de2b32e88dc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Questinol 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Questinol , positive-QTOF	splash10-0udi-0198000000-85818fe9c9cfceb2cae0	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Questinol 10V, Positive-QTOF	splash10-0udi-0039000000-f654aa91cc0047148840	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Questinol 20V, Positive-QTOF	splash10-0udi-0966000000-00f05630751b62675959	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Questinol 40V, Positive-QTOF	splash10-0udi-2390000000-d48689bca35a436fb35c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Questinol 10V, Negative-QTOF	splash10-0002-0090000000-9ea4b6adde6682ba7afa	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Questinol 20V, Negative-QTOF	splash10-00kb-0090000000-e51a2943fecfa03bd146	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Questinol 40V, Negative-QTOF	splash10-0udi-1290000000-9e662abb5d0198c86233	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Questinol 10V, Negative-QTOF	splash10-0002-0090000000-fb4a565723d52a1e4624	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Questinol 20V, Negative-QTOF	splash10-0002-0090000000-43cf03c4cf95bfccc9fa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Questinol 40V, Negative-QTOF	splash10-05mx-0090000000-cbef348c61f6fa56e01d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Questinol 10V, Positive-QTOF	splash10-0udi-0029000000-d8adef1302334501b3dd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Questinol 20V, Positive-QTOF	splash10-0udi-0059000000-334872e52a7d10b873af	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Questinol 40V, Positive-QTOF	splash10-0lna-0490000000-fb5cfd89eb3d06433c8d	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

147621

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1842911

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 Questinol (HMDB0034443)

MOL for HMDB0034443 (Questinol)

3D MOL for HMDB0034443 (Questinol)

3D SDF for HMDB0034443 (Questinol)

3D-SDF for HMDB0034443 (Questinol)

PDB for HMDB0034443 (Questinol)

3D PDB for HMDB0034443 (Questinol)

SMILES for HMDB0034443 (Questinol)

INCHI for HMDB0034443 (Questinol)

Structure for HMDB0034443 (Questinol)

3D Structure for HMDB0034443 (Questinol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra