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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:20 UTC

Update Date

2022-03-07 02:52:38 UTC

HMDB ID

HMDB0030670

Secondary Accession Numbers

HMDB30670

Metabolite Identification

Common Name

Chrysophanol

Description

Chrysophanol, also known as chrysophanic acid or 3-methylchrysazin, belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Thus, chrysophanol is considered to be an aromatic polyketide. Chrysophanol has been detected, but not quantified in, a few different foods, such as docks (Rumex), garden rhubarbs (Rheum rhabarbarum), and sorrels (Rumex acetosa). This could make chrysophanol a potential biomarker for the consumption of these foods. Chrysophanol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Chrysophanol.

Structure

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

HMDB0030670
     RDKit          3D
Chrysophanol
 29 31  0  0  0  0  0  0  0  0999 V2000
    4.6254   -0.8234    0.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2233   -0.2898    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865    1.0538   -0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6977    1.5446   -0.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4461    2.8782   -0.3989 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5957    0.6913   -0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8264   -0.6540    0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1243   -1.1170    0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3293   -1.5276    0.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1507   -2.7527    0.4014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6970   -1.0279    0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7919   -1.8652    0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0699   -1.3547    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3183   -0.0077   -0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2198    0.8185   -0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4095    2.1995   -0.3567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9350    0.3236   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7729    1.1986   -0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9352    2.4331   -0.3619 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0267   -0.6787    1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2605   -0.2586   -0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6567   -1.8932   -0.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8360    1.7176   -0.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2219    3.5162   -0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2611   -2.1788    0.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5825   -2.9146    0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9188   -2.0198    0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3253    0.3877   -0.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3321    2.6008   -0.4258 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  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
  8  2  1  0
 17 11  1  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  8 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
M  END


  Mrv0541 05061305252D          

 19 21  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  7  1  1  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  3  1  0  0  0  0
  9  5  1  0  0  0  0
 10  4  2  0  0  0  0
 11  6  2  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  9  2  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 14  2  0  0  0  0
 19 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030670

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3

> <INCHI_KEY>
LQGUBLBATBMXHT-UHFFFAOYSA-N

> <FORMULA>
C15H10O4

> <MOLECULAR_WEIGHT>
254.2375

> <EXACT_MASS>
254.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
25.51357626545222

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.08

> <JCHEM_LOGP>
4.1249968206666665

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.794259866958585

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.140475575263764

> <JCHEM_PKA_STRONGEST_BASIC>
-4.44676034239525

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
70.15400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
turkey rhubarb

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030670
     RDKit          3D
Chrysophanol
 29 31  0  0  0  0  0  0  0  0999 V2000
    4.6254   -0.8234    0.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2233   -0.2898    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865    1.0538   -0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6977    1.5446   -0.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4461    2.8782   -0.3989 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5957    0.6913   -0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8264   -0.6540    0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1243   -1.1170    0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3293   -1.5276    0.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1507   -2.7527    0.4014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6970   -1.0279    0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7919   -1.8652    0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0699   -1.3547    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3183   -0.0077   -0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2198    0.8185   -0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4095    2.1995   -0.3567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9350    0.3236   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7729    1.1986   -0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9352    2.4331   -0.3619 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0267   -0.6787    1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2605   -0.2586   -0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6567   -1.8932   -0.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8360    1.7176   -0.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2219    3.5162   -0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2611   -2.1788    0.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5825   -2.9146    0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9188   -2.0198    0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3253    0.3877   -0.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3321    2.6008   -0.4258 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  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
  8  2  1  0
 17 11  1  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  8 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 16 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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   3.850   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       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
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    8                                                       
CONECT    4    2   10                                                       
CONECT    5    7    9                                                       
CONECT    6    7   11                                                       
CONECT    7    1    5    6                                                  
CONECT    8    3   12   14                                                  
CONECT    9    5   13   14                                                  
CONECT   10    4   12   16                                                  
CONECT   11    6   13   17                                                  
CONECT   12    8   10   15                                                  
CONECT   13    9   11   15                                                  
CONECT   14    8    9   18                                                  
CONECT   15   12   13   19                                                  
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   14                                                            
CONECT   19   15                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0030670
HETATM    1  C1  UNL     1       4.625  -0.823   0.176  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.223  -0.290   0.083  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.986   1.054  -0.116  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.698   1.545  -0.202  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.446   2.878  -0.399  1.00  0.00           O  
HETATM    6  C5  UNL     1       0.596   0.691  -0.091  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.826  -0.654   0.108  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.124  -1.117   0.190  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.329  -1.528   0.221  1.00  0.00           C  
HETATM   10  O2  UNL     1      -0.151  -2.753   0.401  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.697  -1.028   0.133  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.792  -1.865   0.242  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.070  -1.355   0.153  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.318  -0.008  -0.046  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.220   0.819  -0.154  1.00  0.00           C  
HETATM   16  O3  UNL     1      -3.410   2.199  -0.357  1.00  0.00           O  
HETATM   17  C14 UNL     1      -1.935   0.324  -0.067  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.773   1.199  -0.180  1.00  0.00           C  
HETATM   19  O4  UNL     1      -0.935   2.433  -0.362  1.00  0.00           O  
HETATM   20  H1  UNL     1       5.027  -0.679   1.198  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.260  -0.259  -0.537  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.657  -1.893  -0.149  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.836   1.718  -0.202  1.00  0.00           H  
HETATM   24  H5  UNL     1       2.222   3.516  -0.483  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.261  -2.179   0.346  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.583  -2.915   0.397  1.00  0.00           H  
HETATM   27  H8  UNL     1      -4.919  -2.020   0.239  1.00  0.00           H  
HETATM   28  H9  UNL     1      -5.325   0.388  -0.116  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.332   2.601  -0.426  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3    8
CONECT    3    4   23
CONECT    4    5    6    6
CONECT    5   24
CONECT    6    7   18
CONECT    7    8    8    9
CONECT    8   25
CONECT    9   10   10   11
CONECT   11   12   12   17
CONECT   12   13   26
CONECT   13   14   14   27
CONECT   14   15   28
CONECT   15   16   17   17
CONECT   16   29
CONECT   17   18
CONECT   18   19   19
END

HMDB0030670
     RDKit          3D
Chrysophanol
 29 31  0  0  0  0  0  0  0  0999 V2000
    4.6254   -0.8234    0.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2233   -0.2898    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865    1.0538   -0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6977    1.5446   -0.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4461    2.8782   -0.3989 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5957    0.6913   -0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8264   -0.6540    0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1243   -1.1170    0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3293   -1.5276    0.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1507   -2.7527    0.4014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6970   -1.0279    0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7919   -1.8652    0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0699   -1.3547    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3183   -0.0077   -0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2198    0.8185   -0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4095    2.1995   -0.3567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9350    0.3236   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7729    1.1986   -0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9352    2.4331   -0.3619 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0267   -0.6787    1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2605   -0.2586   -0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6567   -1.8932   -0.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8360    1.7176   -0.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2219    3.5162   -0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2611   -2.1788    0.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5825   -2.9146    0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9188   -2.0198    0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3253    0.3877   -0.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3321    2.6008   -0.4258 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  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
  8  2  1  0
 17 11  1  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  8 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,8-Dihydroxy-3-methyl-9,10-anthracenedione	ChEBI
1,8-Dihydroxy-3-methylanthraquinone	ChEBI
3-Methylchrysazin	ChEBI
Chrysophanic acid	ChEBI
Chrysophansaeure	ChEBI
Chrysophanate	Generator
2-Methyl-4,5-dihydroxyanthraquinone	MeSH
3-Methyl-1,8-dihydroxyanthraquinone	MeSH
Chrysophanic acid, ion (1-)	MeSH
1,8-Dihydroxy-3-methyl-9,10-anthracenedione, 9ci	HMDB
1,8-Dihydroxy-3-methyl-9,10-anthraquinone	HMDB
1,8-Dihydroxy-3-methyl-anthraquinone	HMDB
1,8-Dihydroxy-3-methylanthra-9,10-quinone	HMDB
3-Methyl-1, 8-dihydroxyanthraquinone	HMDB
4, 5-Dihydroxy-2-methylanthraquinone	HMDB
4,5-Dihydroxy-2-methylanthraquinone	HMDB
9,10-Anthracenedione, 1,8-dihydroxy-3-methyl- (9ci)	HMDB
Archinin	HMDB
C.I. natural yellow 23	HMDB
Chrysophanic acid (1,8-dihydroxy-3-methylanthraquinone)	HMDB
Crysophanic acid	HMDB
Crysophanol	HMDB
Rheic acid	HMDB
Rumicin	HMDB
Turkey rhubarb	HMDB

Chemical Formula

C₁₅H₁₀O₄

Average Molecular Weight

254.2375

Monoisotopic Molecular Weight

254.057908808

IUPAC Name

1,8-dihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

turkey rhubarb

CAS Registry Number

481-74-3

SMILES

CC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O

InChI Identifier

InChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3

InChI Key

LQGUBLBATBMXHT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Anthraquinone
9,10-anthraquinone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

hydroxyanthraquinones (CHEBI:3687 )
Anthracenes and phenanthrenes (C10315 )
Anthraquinone type (C10315 )
Anthracenes and phenanthrenes (LMPK13040006 )
a hydroxyanthraquinone (CPD-8216 )

Ontology

Not Available

Exogenous (HMDB: HMDB0030670)

Food

Herb and spice

Herb

Sorrel (FooDB: FOOD00164)

Vegetable

Stalk vegetable

Garden rhubarb (FooDB: FOOD00154)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	200 - 201 °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	0.12 g/L	ALOGPS
logP	3.08	ALOGPS
logP	4.12	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.14	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.15 m³·mol⁻¹	ChemAxon
Polarizability	25.51 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]+	158.12	31661259
DarkChem	[M-H]-	158.7	31661259
DeepCCS	[M+H]+	159.332	30932474
DeepCCS	[M-H]-	156.974	30932474
DeepCCS	[M-2H]-	189.861	30932474
DeepCCS	[M+Na]+	165.426	30932474
AllCCS	[M+H]+	155.9	32859911
AllCCS	[M+H-H2O]+	152.0	32859911
AllCCS	[M+NH4]+	159.6	32859911
AllCCS	[M+Na]+	160.6	32859911
AllCCS	[M-H]-	158.3	32859911
AllCCS	[M+Na-2H]-	157.6	32859911
AllCCS	[M+HCOO]-	156.9	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.	7.11 minutes	32390414
Predicted by Siyang on May 30, 2022	13.6823 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.8 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2672.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	374.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	150.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	219.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	275.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	655.0 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	832.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	73.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1160.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	443.9 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	1521.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	471.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	481.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	422.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	211.9 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	111.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chrysophanol	CC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O	3444.5	Standard polar	33892256
Chrysophanol	CC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O	2228.9	Standard non polar	33892256
Chrysophanol	CC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O	2307.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chrysophanol,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C1	2506.8	Semi standard non polar	33892256
Chrysophanol,1TMS,isomer #2	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C(=O)C2=C1	2503.1	Semi standard non polar	33892256
Chrysophanol,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C(=O)C2=C1	2566.5	Semi standard non polar	33892256
Chrysophanol,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C1	2754.9	Semi standard non polar	33892256
Chrysophanol,1TBDMS,isomer #2	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC=C3C(=O)C2=C1	2774.4	Semi standard non polar	33892256
Chrysophanol,2TBDMS,isomer #1	CC1=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	3053.1	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 - Chrysophanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fc0-0690000000-d56c5b4fdcc7de967ecf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chrysophanol GC-MS (2 TMS) - 70eV, Positive	splash10-05gi-2359000000-d3bd8223a5923410d2a4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chrysophanol 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 - Chrysophanol LC-ESI-QTOF , negative-QTOF	splash10-0udi-0090000000-0a16efeb6df65aacacef	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysophanol LC-ESI-QTOF , negative-QTOF	splash10-0udi-0190000000-10812e976b35a4eda862	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysophanol LC-ESI-QTOF , negative-QTOF	splash10-004i-0490000000-c9aef7073169bd80cd2e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysophanol LC-ESI-QTOF , positive-QTOF	splash10-004i-0900000000-9ac1e0a42128dea2cf82	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysophanol LC-ESI-QTOF , positive-QTOF	splash10-004i-0900000000-cff9163f34bb1966a807	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysophanol 20V, Negative-QTOF	splash10-0udi-0190000000-10812e976b35a4eda862	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysophanol 40V, Negative-QTOF	splash10-004i-0490000000-c9aef7073169bd80cd2e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysophanol 10V, Negative-QTOF	splash10-0udi-0090000000-d81a22c668d9038b248b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysophanol 10V, Positive-QTOF	splash10-004i-0900000000-9ac1e0a42128dea2cf82	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysophanol 20V, Positive-QTOF	splash10-004i-0900000000-cff9163f34bb1966a807	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol 10V, Positive-QTOF	splash10-0a4i-0090000000-e07dfb1bc89242872bd7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol 20V, Positive-QTOF	splash10-0a4i-0090000000-15cdaa0757dfee20a1cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol 40V, Positive-QTOF	splash10-0a4i-5950000000-e1a059b73e79aff8e23e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol 10V, Negative-QTOF	splash10-0udi-0090000000-82cd0ac4ea31f7614f40	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol 20V, Negative-QTOF	splash10-0udi-0090000000-d6372d233a8f6a5cbadb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol 40V, Negative-QTOF	splash10-0pbc-4970000000-8ac19f70333bd7440cef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol 10V, Positive-QTOF	splash10-0a4i-0090000000-88382720cb3b98a4d462	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol 20V, Positive-QTOF	splash10-0a4i-0090000000-e08fea207b7939b57f6d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol 40V, Positive-QTOF	splash10-000i-1940000000-45b0989f4038017840e8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol 10V, Negative-QTOF	splash10-0udi-0090000000-ff2e7266db5d933feb85	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol 20V, Negative-QTOF	splash10-0udi-0090000000-ff2e7266db5d933feb85	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol 40V, Negative-QTOF	splash10-0h00-0590000000-c8e0292c61de829d2a42	2021-09-22	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Chrysophanol

METLIN ID

Not Available

PubChem Compound

10208

PDB ID

Not Available

ChEBI ID

3687

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

Kim SJ, Kim MC, Lee BJ, Park DH, Hong SH, Um JY: Anti-Inflammatory activity of chrysophanol through the suppression of NF-kappaB/caspase-1 activation in vitro and in vivo. Molecules. 2010 Sep 16;15(9):6436-51. doi: 10.3390/molecules15096436. [PubMed:20877234 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Chrysophanol (HMDB0030670)

MOL for HMDB0030670 (Chrysophanol)

3D MOL for HMDB0030670 (Chrysophanol)

3D SDF for HMDB0030670 (Chrysophanol)

3D-SDF for HMDB0030670 (Chrysophanol)

PDB for HMDB0030670 (Chrysophanol)

3D PDB for HMDB0030670 (Chrysophanol)

SMILES for HMDB0030670 (Chrysophanol)

INCHI for HMDB0030670 (Chrysophanol)

Structure for HMDB0030670 (Chrysophanol)

3D Structure for HMDB0030670 (Chrysophanol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra