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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:15:00 UTC

Update Date

2022-03-07 02:54:05 UTC

HMDB ID

HMDB0034409

Secondary Accession Numbers

HMDB34409

Metabolite Identification

Common Name

Rhababerone

Description

Rhababerone 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. Rhababerone has been detected, but not quantified in, garden rhubarbs (Rheum rhabarbarum) and green vegetables. This could make rhababerone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Rhababerone.

Structure

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

HMDB0034409
     RDKit          3D
Rhababerone
 30 32  0  0  0  0  0  0  0  0999 V2000
   -3.9419    0.5042    2.2539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8416    0.4598    1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6060    0.0141    1.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5647   -0.0256    0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7524    0.3708   -0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0070    0.8160   -0.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0603    0.8637   -0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2647    1.3250   -0.4871 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3503    0.3274   -1.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0973    0.7108   -2.7147 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6708   -0.1430   -1.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6752   -0.1702   -2.0898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5690    0.2082   -3.3974 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9412   -0.6302   -1.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1412   -1.0315   -0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1066   -0.9979    0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4222   -1.4199    1.8179 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8637   -0.5506    0.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667   -0.5026    1.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9142   -0.8579    2.3159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5166    0.4733    3.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4997    1.4619    2.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5911   -0.3778    2.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4014   -0.3121    2.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1625    1.1318   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0517    1.3815    0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8752    0.5506   -3.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7641   -0.6704   -2.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1228   -1.3866   -0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9810   -1.5228    2.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  5  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  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
 19 20  2  0
  7  2  1  0
 18 11  1  0
 19  4  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  6 25  1  0
  8 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
M  END

  Mrv0541 05061307472D          

 20 22  0  0  0  0            999 V2000
    5.7158    0.8250    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    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
    5.0013    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
    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
    1.4289    0.0000    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
    5.7158    2.4750    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
  3  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  9  2  0  0  0  0
 13 10  2  0  0  0  0
 13 12  1  0  0  0  0
 14  7  1  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 14  2  0  0  0  0
 20 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034409

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC2=C(C=C1O)C(=O)C1=C(O)C=CC(O)=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O5/c1-6-4-7-8(5-11(6)18)15(20)13-10(17)3-2-9(16)12(13)14(7)19/h2-5,16-18H,1H3

> <INCHI_KEY>
RLTYFLICIIZAKQ-UHFFFAOYSA-N

> <FORMULA>
C15H10O5

> <MOLECULAR_WEIGHT>
270.2369

> <EXACT_MASS>
270.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.49047188729771

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4,6-trihydroxy-7-methyl-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
3.821431499

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.711751722981274

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.627839750920036

> <JCHEM_PKA_STRONGEST_BASIC>
-4.369781830012905

> <JCHEM_POLAR_SURFACE_AREA>
94.82999999999998

> <JCHEM_REFRACTIVITY>
72.1349

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4,6-trihydroxy-7-methylanthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034409
     RDKit          3D
Rhababerone
 30 32  0  0  0  0  0  0  0  0999 V2000
   -3.9419    0.5042    2.2539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8416    0.4598    1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6060    0.0141    1.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5647   -0.0256    0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7524    0.3708   -0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0070    0.8160   -0.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0603    0.8637   -0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2647    1.3250   -0.4871 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3503    0.3274   -1.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0973    0.7108   -2.7147 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6708   -0.1430   -1.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6752   -0.1702   -2.0898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5690    0.2082   -3.3974 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9412   -0.6302   -1.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1412   -1.0315   -0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1066   -0.9979    0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4222   -1.4199    1.8179 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8637   -0.5506    0.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667   -0.5026    1.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9142   -0.8579    2.3159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5166    0.4733    3.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4997    1.4619    2.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5911   -0.3778    2.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4014   -0.3121    2.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1625    1.1318   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0517    1.3815    0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8752    0.5506   -3.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7641   -0.6704   -2.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1228   -1.3866   -0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9810   -1.5228    2.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  5  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  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
 19 20  2  0
  7  2  1  0
 18 11  1  0
 19  4  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  6 25  1  0
  8 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  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   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   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       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   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       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      10.669   4.620   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       5.335   6.160   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    3    9                                                       
CONECT    3    2   10                                                       
CONECT    4    6    7                                                       
CONECT    5    8   11                                                       
CONECT    6    1    4   11                                                  
CONECT    7    4    8   14                                                  
CONECT    8    5    7   15                                                  
CONECT    9    2   12   16                                                  
CONECT   10    3   13   17                                                  
CONECT   11    5    6   18                                                  
CONECT   12    9   13   14                                                  
CONECT   13   10   12   15                                                  
CONECT   14    7   12   19                                                  
CONECT   15    8   13   20                                                  
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0034409
HETATM    1  C1  UNL     1      -3.942   0.504   2.254  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.842   0.460   1.278  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.606   0.014   1.665  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.565  -0.026   0.733  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.752   0.371  -0.558  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.007   0.816  -0.923  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.060   0.864  -0.009  1.00  0.00           C  
HETATM    8  O1  UNL     1      -4.265   1.325  -0.487  1.00  0.00           O  
HETATM    9  C8  UNL     1       0.350   0.327  -1.540  1.00  0.00           C  
HETATM   10  O2  UNL     1       0.097   0.711  -2.715  1.00  0.00           O  
HETATM   11  C9  UNL     1       1.671  -0.143  -1.149  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.675  -0.170  -2.090  1.00  0.00           C  
HETATM   13  O3  UNL     1       2.569   0.208  -3.397  1.00  0.00           O  
HETATM   14  C11 UNL     1       3.941  -0.630  -1.680  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.141  -1.031  -0.384  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.107  -0.998   0.564  1.00  0.00           C  
HETATM   17  O4  UNL     1       3.422  -1.420   1.818  1.00  0.00           O  
HETATM   18  C14 UNL     1       1.864  -0.551   0.179  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.767  -0.503   1.138  1.00  0.00           C  
HETATM   20  O5  UNL     1       0.914  -0.858   2.316  1.00  0.00           O  
HETATM   21  H1  UNL     1      -3.517   0.473   3.272  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.500   1.462   2.077  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.591  -0.378   2.076  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.401  -0.312   2.675  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.162   1.132  -1.946  1.00  0.00           H  
HETATM   26  H6  UNL     1      -5.052   1.382   0.117  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.875   0.551  -3.960  1.00  0.00           H  
HETATM   28  H8  UNL     1       4.764  -0.670  -2.384  1.00  0.00           H  
HETATM   29  H9  UNL     1       5.123  -1.387  -0.073  1.00  0.00           H  
HETATM   30  H10 UNL     1       2.981  -1.523   2.662  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3    7
CONECT    3    4   24
CONECT    4    5    5   19
CONECT    5    6    9
CONECT    6    7    7   25
CONECT    7    8
CONECT    8   26
CONECT    9   10   10   11
CONECT   11   12   12   18
CONECT   12   13   14
CONECT   13   27
CONECT   14   15   15   28
CONECT   15   16   29
CONECT   16   17   18   18
CONECT   17   30
CONECT   18   19
CONECT   19   20   20
END

HMDB0034409
     RDKit          3D
Rhababerone
 30 32  0  0  0  0  0  0  0  0999 V2000
   -3.9419    0.5042    2.2539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8416    0.4598    1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6060    0.0141    1.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5647   -0.0256    0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7524    0.3708   -0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0070    0.8160   -0.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0603    0.8637   -0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2647    1.3250   -0.4871 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3503    0.3274   -1.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0973    0.7108   -2.7147 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6708   -0.1430   -1.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6752   -0.1702   -2.0898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5690    0.2082   -3.3974 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9412   -0.6302   -1.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1412   -1.0315   -0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1066   -0.9979    0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4222   -1.4199    1.8179 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8637   -0.5506    0.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667   -0.5026    1.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9142   -0.8579    2.3159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5166    0.4733    3.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4997    1.4619    2.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5911   -0.3778    2.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4014   -0.3121    2.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1625    1.1318   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0517    1.3815    0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8752    0.5506   -3.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7641   -0.6704   -2.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1228   -1.3866   -0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9810   -1.5228    2.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  5  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  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
 19 20  2  0
  7  2  1  0
 18 11  1  0
 19  4  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  6 25  1  0
  8 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Isoemodin	HMDB

Chemical Formula

C₁₅H₁₀O₅

Average Molecular Weight

270.2369

Monoisotopic Molecular Weight

270.05282343

IUPAC Name

1,4,6-trihydroxy-7-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

1,4,6-trihydroxy-7-methylanthracene-9,10-dione

CAS Registry Number

Not Available

SMILES

CC1=CC2=C(C=C1O)C(=O)C1=C(O)C=CC(O)=C1C2=O

InChI Identifier

InChI=1S/C15H10O5/c1-6-4-7-8(5-11(6)18)15(20)13-10(17)3-2-9(16)12(13)14(7)19/h2-5,16-18H,1H3

InChI Key

RLTYFLICIIZAKQ-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
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034409)
Cell membrane (HMDB: HMDB0034409)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034409)

Source

Exogenous

Exogenous (HMDB: HMDB0034409)

Food

Food (HMDB: HMDB0034409)

Vegetable

Stalk vegetable

Garden rhubarb (FooDB: FOOD00154)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0034409)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034409)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	223 - 224 °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	0.22 g/L	ALOGPS
logP	2.64	ALOGPS
logP	3.82	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.63	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	72.13 m³·mol⁻¹	ChemAxon
Polarizability	26.49 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	161.51	31661259
DarkChem	[M-H]-	161.676	31661259
DeepCCS	[M+H]+	159.928	30932474
DeepCCS	[M-H]-	157.57	30932474
DeepCCS	[M-2H]-	190.456	30932474
DeepCCS	[M+Na]+	166.021	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]-	160.8	32859911
AllCCS	[M+Na-2H]-	160.0	32859911
AllCCS	[M+HCOO]-	159.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rhababerone	CC1=CC2=C(C=C1O)C(=O)C1=C(O)C=CC(O)=C1C2=O	3730.0	Standard polar	33892256
Rhababerone	CC1=CC2=C(C=C1O)C(=O)C1=C(O)C=CC(O)=C1C2=O	2373.9	Standard non polar	33892256
Rhababerone	CC1=CC2=C(C=C1O)C(=O)C1=C(O)C=CC(O)=C1C2=O	2780.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Rhababerone,1TMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C)C(=O)C1=C(O)C=CC(O)=C1C2=O	2798.4	Semi standard non polar	33892256
Rhababerone,1TMS,isomer #2	CC1=CC2=C(C=C1O)C(=O)C1=C(O[Si](C)(C)C)C=CC(O)=C1C2=O	2760.7	Semi standard non polar	33892256
Rhababerone,1TMS,isomer #3	CC1=CC2=C(C=C1O)C(=O)C1=C(O)C=CC(O[Si](C)(C)C)=C1C2=O	2759.8	Semi standard non polar	33892256
Rhababerone,2TMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C)C(=O)C1=C(O[Si](C)(C)C)C=CC(O)=C1C2=O	2766.1	Semi standard non polar	33892256
Rhababerone,2TMS,isomer #2	CC1=CC2=C(C=C1O[Si](C)(C)C)C(=O)C1=C(O)C=CC(O[Si](C)(C)C)=C1C2=O	2765.6	Semi standard non polar	33892256
Rhababerone,2TMS,isomer #3	CC1=CC2=C(C=C1O)C(=O)C1=C(O[Si](C)(C)C)C=CC(O[Si](C)(C)C)=C1C2=O	2716.3	Semi standard non polar	33892256
Rhababerone,3TMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C)C(=O)C1=C(O[Si](C)(C)C)C=CC(O[Si](C)(C)C)=C1C2=O	2731.1	Semi standard non polar	33892256
Rhababerone,1TBDMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(=O)C1=C(O)C=CC(O)=C1C2=O	3064.7	Semi standard non polar	33892256
Rhababerone,1TBDMS,isomer #2	CC1=CC2=C(C=C1O)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=CC(O)=C1C2=O	3030.6	Semi standard non polar	33892256
Rhababerone,1TBDMS,isomer #3	CC1=CC2=C(C=C1O)C(=O)C1=C(O)C=CC(O[Si](C)(C)C(C)(C)C)=C1C2=O	3029.9	Semi standard non polar	33892256
Rhababerone,2TBDMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=CC(O)=C1C2=O	3296.1	Semi standard non polar	33892256
Rhababerone,2TBDMS,isomer #2	CC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(=O)C1=C(O)C=CC(O[Si](C)(C)C(C)(C)C)=C1C2=O	3301.6	Semi standard non polar	33892256
Rhababerone,2TBDMS,isomer #3	CC1=CC2=C(C=C1O)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C2=O	3249.5	Semi standard non polar	33892256
Rhababerone,3TBDMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C2=O	3474.2	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 - Rhababerone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0016-0690000000-4eb0d3c8cd52d8237fc4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhababerone GC-MS (3 TMS) - 70eV, Positive	splash10-024i-4323900000-dd2e5f72f17bc37fbd6f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhababerone 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 - Rhababerone 10V, Positive-QTOF	splash10-00di-0090000000-2f705c3a91e1c2c554ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhababerone 20V, Positive-QTOF	splash10-0fe0-0690000000-94d13d688157d35d8f68	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhababerone 40V, Positive-QTOF	splash10-0udi-4490000000-b8d6e6170e8c1716ebd4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhababerone 10V, Negative-QTOF	splash10-014i-0090000000-d802fb07e37949fa5ba9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhababerone 20V, Negative-QTOF	splash10-014i-0090000000-78a559392a9ce32f6969	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhababerone 40V, Negative-QTOF	splash10-0k9l-3690000000-edb6fb0ee85a7cb938e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhababerone 10V, Positive-QTOF	splash10-00di-0090000000-ae6e5e86465295cd0332	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhababerone 20V, Positive-QTOF	splash10-00di-0090000000-c37af8cda272440a19dc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhababerone 40V, Positive-QTOF	splash10-052r-0930000000-d5942073274c914ab6da	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhababerone 10V, Negative-QTOF	splash10-014i-0090000000-4e65ba44fc45f7e80f5a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhababerone 20V, Negative-QTOF	splash10-014i-0090000000-4e65ba44fc45f7e80f5a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhababerone 40V, Negative-QTOF	splash10-000i-0690000000-c45bfa76979dce8d8095	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012800

KNApSAcK ID

Not Available

Chemspider ID

30777054

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12310964

PDB ID

Not Available

ChEBI ID

174543

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 Rhababerone (HMDB0034409)

MOL for HMDB0034409 (Rhababerone)

3D MOL for HMDB0034409 (Rhababerone)

3D SDF for HMDB0034409 (Rhababerone)

3D-SDF for HMDB0034409 (Rhababerone)

PDB for HMDB0034409 (Rhababerone)

3D PDB for HMDB0034409 (Rhababerone)

SMILES for HMDB0034409 (Rhababerone)

INCHI for HMDB0034409 (Rhababerone)

Structure for HMDB0034409 (Rhababerone)

3D Structure for HMDB0034409 (Rhababerone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra