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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:52:24 UTC

Update Date

2022-03-07 02:53:30 UTC

HMDB ID

HMDB0032876

Secondary Accession Numbers

HMDB32876

Metabolite Identification

Common Name

Rhein

Description

Rhein belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system. Thus, rhein is considered to be an aromatic polyketide. Rhein has been detected, but not quantified in, a few different foods, such as docks (Rumex), garden rhubarbs (Rheum rhabarbarum), and green vegetables. This could make rhein a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Rhein.

Structure

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

HMDB0032876
     RDKit          3D
Rhein
 29 31  0  0  0  0  0  0  0  0999 V2000
    4.6255   -2.2199    0.5012 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4249   -1.1004    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5188   -0.3855   -0.4613 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0879   -0.5350   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8683    0.7126   -0.6478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6247    1.2675   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3521    2.5094   -1.2980 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5358    0.5305   -0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7100   -0.7079    0.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9894   -1.2289    0.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4456   -1.4276    0.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2721   -2.5833    1.2693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7914   -0.8846    0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8798   -1.5963    1.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1390   -1.0702    1.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3477    0.1531    0.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2735    0.8972    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5308    2.1120   -0.5158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9843    0.3717    0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8147    1.0877   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9429    2.2280   -0.8863 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7489    0.5499   -0.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7068    1.2844   -1.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1682    3.0379   -1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1209   -2.2099    0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7422   -2.5757    1.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0267   -1.6072    1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3352    0.6130    0.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9563    2.7779   -0.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 10  4  1  0
 19 13  1  0
 20  8  1  0
  3 22  1  0
  5 23  1  0
  7 24  1  0
 10 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 18 29  1  0
M  END


  Mrv0541 05061306462D          

 21 23  0  0  0  0            999 V2000
    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
    0.0000    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
    1.4289    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
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  9  3  2  0  0  0  0
 10  5  2  0  0  0  0
 11  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  6  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 13  2  0  0  0  0
 19 14  2  0  0  0  0
 20 15  2  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032876

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21)

> <INCHI_KEY>
FCDLCPWAQCPTKC-UHFFFAOYSA-N

> <FORMULA>
C15H8O6

> <MOLECULAR_WEIGHT>
284.2204

> <EXACT_MASS>
284.032087988

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
26.620896626424145

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
3.269158339333333

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.088754562545892

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3988243915354075

> <JCHEM_PKA_STRONGEST_BASIC>
-4.446915529565238

> <JCHEM_POLAR_SURFACE_AREA>
111.89999999999999

> <JCHEM_REFRACTIVITY>
72.369

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
monorhein

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032876
     RDKit          3D
Rhein
 29 31  0  0  0  0  0  0  0  0999 V2000
    4.6255   -2.2199    0.5012 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4249   -1.1004    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5188   -0.3855   -0.4613 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0879   -0.5350   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8683    0.7126   -0.6478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6247    1.2675   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3521    2.5094   -1.2980 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5358    0.5305   -0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7100   -0.7079    0.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9894   -1.2289    0.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4456   -1.4276    0.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2721   -2.5833    1.2693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7914   -0.8846    0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8798   -1.5963    1.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1390   -1.0702    1.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3477    0.1531    0.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2735    0.8972    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5308    2.1120   -0.5158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9843    0.3717    0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8147    1.0877   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9429    2.2280   -0.8863 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7489    0.5499   -0.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7068    1.2844   -1.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1682    3.0379   -1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1209   -2.2099    0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7422   -2.5757    1.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0267   -1.6072    1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3352    0.6130    0.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9563    2.7779   -0.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 10  4  1  0
 19 13  1  0
 20  8  1  0
  3 22  1  0
  5 23  1  0
  7 24  1  0
 10 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 18 29  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       9.336   2.310   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       1.334   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       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   4.620   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       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002   6.160   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       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       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    7                                                       
CONECT    3    1    9                                                       
CONECT    4    6    8                                                       
CONECT    5    6   10                                                       
CONECT    6    4    5   15                                                  
CONECT    7    2   11   13                                                  
CONECT    8    4   12   13                                                  
CONECT    9    3   11   16                                                  
CONECT   10    5   12   17                                                  
CONECT   11    7    9   14                                                  
CONECT   12    8   10   14                                                  
CONECT   13    7    8   18                                                  
CONECT   14   11   12   19                                                  
CONECT   15    6   20   21                                                  
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21   15                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0032876
HETATM    1  O1  UNL     1       4.626  -2.220   0.501  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.425  -1.100   0.005  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.519  -0.386  -0.461  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.088  -0.535  -0.094  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.868   0.713  -0.648  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.625   1.267  -0.754  1.00  0.00           C  
HETATM    7  O3  UNL     1       1.352   2.509  -1.298  1.00  0.00           O  
HETATM    8  C5  UNL     1       0.536   0.530  -0.278  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.710  -0.708   0.277  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.989  -1.229   0.363  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.446  -1.428   0.753  1.00  0.00           C  
HETATM   12  O4  UNL     1      -0.272  -2.583   1.269  1.00  0.00           O  
HETATM   13  C9  UNL     1      -1.791  -0.885   0.665  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.880  -1.596   1.129  1.00  0.00           C  
HETATM   15  C11 UNL     1      -4.139  -1.070   1.039  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.348   0.153   0.495  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.273   0.897   0.018  1.00  0.00           C  
HETATM   18  O5  UNL     1      -3.531   2.112  -0.516  1.00  0.00           O  
HETATM   19  C14 UNL     1      -1.984   0.372   0.104  1.00  0.00           C  
HETATM   20  C15 UNL     1      -0.815   1.088  -0.372  1.00  0.00           C  
HETATM   21  O6  UNL     1      -0.943   2.228  -0.886  1.00  0.00           O  
HETATM   22  H1  UNL     1       5.749   0.550  -0.109  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.707   1.284  -1.016  1.00  0.00           H  
HETATM   24  H3  UNL     1       2.168   3.038  -1.644  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.121  -2.210   0.803  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.742  -2.576   1.568  1.00  0.00           H  
HETATM   27  H6  UNL     1      -5.027  -1.607   1.397  1.00  0.00           H  
HETATM   28  H7  UNL     1      -5.335   0.613   0.402  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.956   2.778  -0.896  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   22
CONECT    4    5    5   10
CONECT    5    6   23
CONECT    6    7    8    8
CONECT    7   24
CONECT    8    9   20
CONECT    9   10   10   11
CONECT   10   25
CONECT   11   12   12   13
CONECT   13   14   14   19
CONECT   14   15   26
CONECT   15   16   16   27
CONECT   16   17   28
CONECT   17   18   19   19
CONECT   18   29
CONECT   19   20
CONECT   20   21   21
END

HMDB0032876
     RDKit          3D
Rhein
 29 31  0  0  0  0  0  0  0  0999 V2000
    4.6255   -2.2199    0.5012 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4249   -1.1004    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5188   -0.3855   -0.4613 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0879   -0.5350   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8683    0.7126   -0.6478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6247    1.2675   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3521    2.5094   -1.2980 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5358    0.5305   -0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7100   -0.7079    0.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9894   -1.2289    0.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4456   -1.4276    0.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2721   -2.5833    1.2693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7914   -0.8846    0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8798   -1.5963    1.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1390   -1.0702    1.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3477    0.1531    0.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2735    0.8972    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5308    2.1120   -0.5158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9843    0.3717    0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8147    1.0877   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9429    2.2280   -0.8863 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7489    0.5499   -0.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7068    1.2844   -1.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1682    3.0379   -1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1209   -2.2099    0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7422   -2.5757    1.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0267   -1.6072    1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3352    0.6130    0.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9563    2.7779   -0.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 10  4  1  0
 19 13  1  0
 20  8  1  0
  3 22  1  0
  5 23  1  0
  7 24  1  0
 10 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 18 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,8-Dihydroxy-3-carboxyl anthraquinone	HMDB
1,8-Dihydroxy-3-carboxyl-9,10-anthraquinone	HMDB, MeSH
1,8-Dihydroxyanthraquinone-3-carboxylic acid	HMDB
4, 5-Dihydroxyanthraquinone-2-carboxylic acid	HMDB
4,5-Dihydroxy-2-anthraquinonecarboxylic acid	HMDB
4,5-DiOH-anthraquinone-2-COOH	HMDB
9,10-dihydro-4,5-Dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid, 9ci	HMDB
9,10-dihydro-4,5-Dihydroxy-9,10-dioxo-2-anthroic acid	HMDB
Cassic acid	HMDB
Chrysazin-3-carboxylic acid	HMDB
Dipropionyl rhein	HMDB, MeSH
Monorhein	HMDB
Rhein (1,8-dihydroxy-3-carboxyl anthraquinone)	HMDB
Rhubarb yellow	HMDB
4,5-Dihydroxyanthraquinone-2-carboxylic acid	MeSH, HMDB

Chemical Formula

C₁₅H₈O₆

Average Molecular Weight

284.2204

Monoisotopic Molecular Weight

284.032087988

IUPAC Name

4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Traditional Name

monorhein

CAS Registry Number

478-43-3

SMILES

OC(=O)C1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O

InChI Identifier

InChI=1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21)

InChI Key

FCDLCPWAQCPTKC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Anthracenecarboxylic acids and derivatives

Direct Parent

Anthracenecarboxylic acids

Alternative Parents

Substituents

Anthracene carboxylic acid
9,10-anthraquinone
Anthraquinone
2-naphthalenecarboxylic acid
2-naphthalenecarboxylic acid or derivatives
Hydroxybenzoic acid
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

anthracenes (CHEBI:8825 )
Anthracenes and phenanthrenes (C10401 )
Anthraquinone type (C10401 )
Anthracenes and phenanthrenes (LMPK13040015 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032876)
Cytoplasm (HMDB: HMDB0032876)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032876)

Source

Exogenous

Exogenous (HMDB: HMDB0032876)

Food

Food (HMDB: HMDB0032876)

Vegetable

Stalk vegetable

Garden rhubarb (FooDB: FOOD00154)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Herb and spice

Herb

Dock (FooDB: FOOD00350)

Endogenous

Plant

Plant (HMDB: HMDB0032876)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0032876)

Antineoplastic agent

Antitumor (HMDB: HMDB0032876)

Antiviral agent (HMDB: HMDB0032876)

Agriculture

Pesticide

Fungicide (HMDB: HMDB0032876)

Pesticide (HMDB: HMDB0032876)

Biological role

Nutrient (HMDB: HMDB0032876)
Calcium antagonist (HMDB: HMDB0032876)
Anti bacterial (HMDB: HMDB0032876)
Anti carcinomic (HMDB: HMDB0032876)
Anti cariogenic (HMDB: HMDB0032876)
Anti cytomegalovirus (HMDB: HMDB0032876)
Anti neoplastic (HMDB: HMDB0032876)
Anti plaque (HMDB: HMDB0032876)
Anti septic (HMDB: HMDB0032876)
Candidicide (HMDB: HMDB0032876)
Cathartic (HMDB: HMDB0032876)
Cytotoxic (HMDB: HMDB0032876)
Purgative (HMDB: HMDB0032876)

Modulator

Inhibitor

Proteinase inhibitor (HMDB: HMDB0032876)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	321 °C	Not Available
Boiling Point	597.00 to 598.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	2.45 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.290 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	2.18	ALOGPS
logP	3.27	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.37 m³·mol⁻¹	ChemAxon
Polarizability	26.62 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]+	163.895	31661259
DarkChem	[M-H]-	165.307	31661259
DeepCCS	[M+H]+	160.892	30932474
DeepCCS	[M-H]-	158.534	30932474
DeepCCS	[M-2H]-	192.206	30932474
DeepCCS	[M+Na]+	167.433	30932474
AllCCS	[M+H]+	162.5	32859911
AllCCS	[M+H-H2O]+	158.9	32859911
AllCCS	[M+NH4]+	165.9	32859911
AllCCS	[M+Na]+	166.9	32859911
AllCCS	[M-H]-	162.4	32859911
AllCCS	[M+Na-2H]-	161.6	32859911
AllCCS	[M+HCOO]-	160.8	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.	5.74 minutes	32390414
Predicted by Siyang on May 30, 2022	11.5351 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.43 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	38.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2424.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	312.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	114.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	187.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	142.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	500.2 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	662.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	85.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	863.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	374.4 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	1421.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	374.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	412.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	500.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	187.0 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	214.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rhein	OC(=O)C1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O	4047.2	Standard polar	33892256
Rhein	OC(=O)C1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O	2123.4	Standard non polar	33892256
Rhein	OC(=O)C1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O	2626.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Rhein,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C1	2825.6	Semi standard non polar	33892256
Rhein,1TMS,isomer #2	C[Si](C)(C)OC1=CC(C(=O)O)=CC2=C1C(=O)C1=C(O)C=CC=C1C2=O	2773.3	Semi standard non polar	33892256
Rhein,1TMS,isomer #3	C[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O)C=C(C(=O)O)C=C1C2=O	2782.1	Semi standard non polar	33892256
Rhein,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C1	2799.8	Semi standard non polar	33892256
Rhein,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C(=O)C2=C1	2824.2	Semi standard non polar	33892256
Rhein,2TMS,isomer #3	C[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(C(=O)O)C=C1C2=O	2806.1	Semi standard non polar	33892256
Rhein,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C(=O)C2=C1	2854.9	Semi standard non polar	33892256
Rhein,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C1	3092.4	Semi standard non polar	33892256
Rhein,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(C(=O)O)=CC2=C1C(=O)C1=C(O)C=CC=C1C2=O	3017.5	Semi standard non polar	33892256
Rhein,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O)C=C(C(=O)O)C=C1C2=O	3028.0	Semi standard non polar	33892256
Rhein,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C1	3281.1	Semi standard non polar	33892256
Rhein,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC=C3C(=O)C2=C1	3328.8	Semi standard non polar	33892256
Rhein,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(C(=O)O)C=C1C2=O	3316.1	Semi standard non polar	33892256
Rhein,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC=C3C(=O)C2=C1	3544.1	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 - Rhein GC-MS (Non-derivatized) - 70eV, Positive	splash10-07cv-0590000000-afcf37d77e69652177f2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhein GC-MS (3 TMS) - 70eV, Positive	splash10-024r-4102900000-c5b546456fd0d7644f8a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhein 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 - Rhein LC-ESI-QQ , negative-QTOF	splash10-001i-0090000000-9ac3e7791e49a21d3f7e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhein LC-ESI-QQ , negative-QTOF	splash10-000i-0090000000-8a0c3c4f77482fc05626	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhein LC-ESI-QQ , negative-QTOF	splash10-000i-0190000000-a217257577bda56ddeb9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhein LC-ESI-QQ , negative-QTOF	splash10-001i-0950000000-f5cac5a3a6c78fc4ed85	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhein LC-ESI-QQ , negative-QTOF	splash10-001i-0910000000-4671892dc0bcf7214bc0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhein LC-ESI-QTOF , negative-QTOF	splash10-000i-0090000000-5f27d9cb7d81c2b3da8d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhein LC-ESI-QTOF , negative-QTOF	splash10-000i-0190000000-87c468c6073faf9e5fae	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhein LC-ESI-QTOF , negative-QTOF	splash10-001i-0920000000-0b0038f124d8c1494117	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhein LC-ESI-QTOF , positive-QTOF	splash10-000i-0090000000-a2294fd7666d75dbcbd0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhein , positive-QTOF	splash10-052u-0890000000-5f1951e9414e26b22db9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhein 40V, Negative-QTOF	splash10-001i-0920000000-5757933ef5a7532b4ef1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhein 10V, Positive-QTOF	splash10-000i-0090000000-a2294fd7666d75dbcbd0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhein 20V, Positive-QTOF	splash10-000l-0090000000-a2178fdd7c56081cab09	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhein 10V, Positive-QTOF	splash10-000i-0090000000-8f070d596b12739e117e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhein 40V, Positive-QTOF	splash10-0ac0-0910000000-a9cb6e465076d6963a82	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhein 10V, Negative-QTOF	splash10-000i-0090000000-2c3cbe9c71ab4af87a66	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhein 20V, Negative-QTOF	splash10-000i-0290000000-66c888a0ecf96ae01c8c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhein 40V, Negative-QTOF	splash10-001i-0920000000-eb6d2ee2a66f5ba2d590	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rhein 10V, Negative-QTOF	splash10-000i-0090000000-467e222d330c2d39d5b1	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhein 10V, Positive-QTOF	splash10-00kr-0090000000-6163d091b67836bcff63	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhein 20V, Positive-QTOF	splash10-014r-0190000000-bd5d0494f66cd7d5828c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhein 40V, Positive-QTOF	splash10-00rl-2290000000-33f58cc10ba47d1b818a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhein 10V, Negative-QTOF	splash10-001i-0090000000-05c98e64e03e092b3975	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhein 20V, Negative-QTOF	splash10-0019-0090000000-ec4cf61d964a40527521	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhein 40V, Negative-QTOF	splash10-00ku-4390000000-5d5e000d8c2e171dd309	2015-04-25	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

DB13174

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

Rhein

METLIN ID

Not Available

PubChem Compound

10168

PDB ID

RHN

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1280361

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Didry N, Dubreuil L, Pinkas M: Activity of anthraquinonic and naphthoquinonic compounds on oral bacteria. Pharmazie. 1994 Sep;49(9):681-3. [PubMed:7972313 ]
Stermitz FR, Cashman KK, Halligan KM, Morel C, Tegos GP, Lewis K: Polyacylated neohesperidosides from Geranium caespitosum: bacterial multidrug resistance pump inhibitors. Bioorg Med Chem Lett. 2003 Jun 2;13(11):1915-8. [PubMed:12749897 ]
Izzo AA, Mascolo N, Capasso F: Effect of sodium rhein on electrically-evoked and agonist-induced contractions of the guinea-pig isolated ileal circular muscle. Br J Pharmacol. 1998 Jun;124(4):825-31. [PubMed:9690877 ]
Kuo PL, Hsu YL, Ng LT, Lin CC: Rhein inhibits the growth and induces the apoptosis of Hep G2 cells. Planta Med. 2004 Jan;70(1):12-6. [PubMed:14765286 ]
Chang CY, Chan HL, Lin HY, Way TD, Kao MC, Song MZ, Lin YJ, Lin CW: Rhein induces apoptosis in human breast cancer cells. Evid Based Complement Alternat Med. 2012;2012:952504. doi: 10.1155/2012/952504. Epub 2011 Oct 5. [PubMed:22007260 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Rhein (HMDB0032876)

MOL for HMDB0032876 (Rhein)

3D MOL for HMDB0032876 (Rhein)

3D SDF for HMDB0032876 (Rhein)

3D-SDF for HMDB0032876 (Rhein)

PDB for HMDB0032876 (Rhein)

3D PDB for HMDB0032876 (Rhein)

SMILES for HMDB0032876 (Rhein)

INCHI for HMDB0032876 (Rhein)

Structure for HMDB0032876 (Rhein)

3D Structure for HMDB0032876 (Rhein)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra