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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:12:02 UTC

Update Date

2021-09-26 23:01:33 UTC

HMDB ID

HMDB0250218

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Chrysophanol-9-anthrone

Description

Chrysophanol-9-anthrone, also known as chrysarobin or chrysothrone, belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings. Thus, chrysophanol-9-anthrone is considered to be an aromatic polyketide. Chrysophanol-9-anthrone has been detected, but not quantified in, sorrels (Rumex acetosa). This could make chrysophanol-9-anthrone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Chrysophanol-9-anthrone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Chrysophanol-9-anthrone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Chrysophanol-9-anthrone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0250218
     RDKit          3D
Chrysophanol-9-anthrone
 30 32  0  0  0  0  0  0  0  0999 V2000
    4.6512    0.2016   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2270   -0.0562   -0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8929   -0.8784    0.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5538   -1.1340    1.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3534   -1.9648    2.3911 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5306   -0.5426    0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8504    0.2877   -0.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1988    0.5297   -0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2053    0.9472   -1.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5824    0.6932   -0.8010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5799    1.3352   -1.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8802    1.1210   -1.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2677    0.3054   -0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2935   -0.3509    0.5713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6470   -1.1564    1.5900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9538   -0.1236    0.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765   -0.7714    0.9955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1578   -1.5185    1.9384 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9752    1.2127   -0.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2814   -0.5072    0.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8510   -0.0483   -1.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6926   -1.3509    1.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520   -2.2728    2.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603    1.1927   -1.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0692    2.0778   -1.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0043    0.7427   -2.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2633    1.9871   -2.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6380    1.6307   -1.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2948    0.1218    0.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2656   -1.7106    2.2652 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  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
  8  2  1  0
 16 10  1  0
 17  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  5 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
M  END


  Mrv1533004241519242D          

 18 20  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
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    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
    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
 13 17  1  0  0  0  0
  4 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250218

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(O)=C2C(=O)C3=C(CC2=C1)C=CC=C3O

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O3/c1-8-5-10-7-9-3-2-4-11(16)13(9)15(18)14(10)12(17)6-8/h2-6,16-17H,7H2,1H3

> <INCHI_KEY>
ZZBWSNKBZKPGAK-UHFFFAOYSA-N

> <FORMULA>
C15H12O3

> <MOLECULAR_WEIGHT>
240.258

> <EXACT_MASS>
240.078644246

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
25.444845063353036

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,8-dihydroxy-3-methyl-9,10-dihydroanthracen-9-one

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
4.757437810333332

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.170790312219424

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.518715962279453

> <JCHEM_PKA_STRONGEST_BASIC>
-5.615219066401516

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
69.31570000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chrysarobin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250218
     RDKit          3D
Chrysophanol-9-anthrone
 30 32  0  0  0  0  0  0  0  0999 V2000
    4.6512    0.2016   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2270   -0.0562   -0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8929   -0.8784    0.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5538   -1.1340    1.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3534   -1.9648    2.3911 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5306   -0.5426    0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8504    0.2877   -0.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1988    0.5297   -0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2053    0.9472   -1.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5824    0.6932   -0.8010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5799    1.3352   -1.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8802    1.1210   -1.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2677    0.3054   -0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2935   -0.3509    0.5713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6470   -1.1564    1.5900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9538   -0.1236    0.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765   -0.7714    0.9955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1578   -1.5185    1.9384 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9752    1.2127   -0.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2814   -0.5072    0.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8510   -0.0483   -1.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6926   -1.3509    1.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520   -2.2728    2.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603    1.1927   -1.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0692    2.0778   -1.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0043    0.7427   -2.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2633    1.9871   -2.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6380    1.6307   -1.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2948    0.1218    0.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2656   -1.7106    2.2652 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  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
  8  2  1  0
 16 10  1  0
 17  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  5 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         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       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -0.000   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  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    5   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    9                                                       
CONECT   17   13                                                            
CONECT   18    4                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0250218
HETATM    1  C1  UNL     1       4.651   0.202  -0.446  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.227  -0.056  -0.066  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.893  -0.878   0.973  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.554  -1.134   1.347  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.353  -1.965   2.391  1.00  0.00           O  
HETATM    6  C5  UNL     1       0.531  -0.543   0.652  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.850   0.288  -0.396  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.199   0.530  -0.754  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.205   0.947  -1.175  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.582   0.693  -0.801  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.580   1.335  -1.560  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.880   1.121  -1.239  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.268   0.305  -0.207  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.293  -0.351   0.571  1.00  0.00           C  
HETATM   15  O2  UNL     1      -3.647  -1.156   1.590  1.00  0.00           O  
HETATM   16  C14 UNL     1      -1.954  -0.124   0.232  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.876  -0.771   0.995  1.00  0.00           C  
HETATM   18  O3  UNL     1      -1.158  -1.518   1.938  1.00  0.00           O  
HETATM   19  H1  UNL     1       4.975   1.213  -0.185  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.281  -0.507   0.151  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.851  -0.048  -1.506  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.693  -1.351   1.529  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.552  -2.273   2.808  1.00  0.00           H  
HETATM   24  H6  UNL     1       2.360   1.193  -1.587  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.069   2.078  -1.101  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.004   0.743  -2.257  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.263   1.987  -2.386  1.00  0.00           H  
HETATM   28  H10 UNL     1      -4.638   1.631  -1.843  1.00  0.00           H  
HETATM   29  H11 UNL     1      -5.295   0.122   0.065  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.266  -1.711   2.265  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    8
CONECT    3    4   22
CONECT    4    5    6    6
CONECT    5   23
CONECT    6    7   17
CONECT    7    8    8    9
CONECT    8   24
CONECT    9   10   25   26
CONECT   10   11   11   16
CONECT   11   12   27
CONECT   12   13   13   28
CONECT   13   14   29
CONECT   14   15   16   16
CONECT   15   30
CONECT   16   17
CONECT   17   18   18
END

HMDB0250218
     RDKit          3D
Chrysophanol-9-anthrone
 30 32  0  0  0  0  0  0  0  0999 V2000
    4.6512    0.2016   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2270   -0.0562   -0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8929   -0.8784    0.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5538   -1.1340    1.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3534   -1.9648    2.3911 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5306   -0.5426    0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8504    0.2877   -0.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1988    0.5297   -0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2053    0.9472   -1.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5824    0.6932   -0.8010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5799    1.3352   -1.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8802    1.1210   -1.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2677    0.3054   -0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2935   -0.3509    0.5713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6470   -1.1564    1.5900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9538   -0.1236    0.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765   -0.7714    0.9955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1578   -1.5185    1.9384 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9752    1.2127   -0.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2814   -0.5072    0.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8510   -0.0483   -1.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6926   -1.3509    1.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520   -2.2728    2.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603    1.1927   -1.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0692    2.0778   -1.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0043    0.7427   -2.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2633    1.9871   -2.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6380    1.6307   -1.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2948    0.1218    0.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2656   -1.7106    2.2652 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  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
  8  2  1  0
 16 10  1  0
 17  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  5 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,8-Dihydroxy-3-methyl-9(10H)-anthracenone	ChEBI
1,8-Dihydroxy-3-methylanthrone	ChEBI
Chrysarobin	ChEBI
Chrysophanic acid 9-anthrone	ChEBI
Chrysophanol anthrone	ChEBI
Chrysothrone	ChEBI
Chrysophanate 9-anthrone	Generator
Chrysophanic acid-9-anthrone	MeSH

Chemical Formula

C₁₅H₁₂O₃

Average Molecular Weight

240.258

Monoisotopic Molecular Weight

240.078644246

IUPAC Name

1,8-dihydroxy-3-methyl-9,10-dihydroanthracen-9-one

Traditional Name

chrysarobin

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=C2C(=O)C3=C(CC2=C1)C=CC=C3O

InChI Identifier

InChI=1S/C15H12O3/c1-8-5-10-7-9-3-2-4-11(16)13(9)15(18)14(10)12(17)6-8/h2-6,16-17H,7H2,1H3

InChI Key

ZZBWSNKBZKPGAK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Not Available

Direct Parent

Anthracenes

Alternative Parents

Substituents

Anthracene
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

anthracenes (CHEBI:3686 )
Anthracenes and phenanthrenes (C10314 )
Anthrone type (C10314 )
Anthracenes and phenanthrenes (LMPK13040005 )
a polyketide (CPD-11587 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0250218)

Food

Herb and spice

Herb

Sorrel (FooDB: FOOD00164)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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
logP	2.99	ALOGPS
logP	4.76	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	8.52	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.32 m³·mol⁻¹	ChemAxon
Polarizability	25.44 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
DeepCCS	[M+H]+	154.347	30932474
DeepCCS	[M-H]-	151.953	30932474
DeepCCS	[M-2H]-	184.838	30932474
DeepCCS	[M+Na]+	160.404	30932474
AllCCS	[M+H]+	153.2	32859911
AllCCS	[M+H-H2O]+	149.2	32859911
AllCCS	[M+NH4]+	157.0	32859911
AllCCS	[M+Na]+	158.1	32859911
AllCCS	[M-H]-	156.6	32859911
AllCCS	[M+Na-2H]-	155.9	32859911
AllCCS	[M+HCOO]-	155.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	13.9507 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.2 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2226.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	394.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	172.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	230.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	307.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	662.0 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	720.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	71.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1226.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	480.4 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	1480.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	426.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	440.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	381.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	168.7 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	35.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chrysophanol-9-anthrone	CC1=CC(O)=C2C(=O)C3=C(CC2=C1)C=CC=C3O	3544.9	Standard polar	33892256
Chrysophanol-9-anthrone	CC1=CC(O)=C2C(=O)C3=C(CC2=C1)C=CC=C3O	2192.6	Standard non polar	33892256
Chrysophanol-9-anthrone	CC1=CC(O)=C2C(=O)C3=C(CC2=C1)C=CC=C3O	2273.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Chrysophanol-9-anthrone GC-MS (Non-derivatized) - 70eV, Positive	splash10-03ec-0690000000-f4bb421b29a03b829ff9	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chrysophanol-9-anthrone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chrysophanol-9-anthrone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chrysophanol-9-anthrone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chrysophanol-9-anthrone GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chrysophanol-9-anthrone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chrysophanol-9-anthrone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chrysophanol-9-anthrone GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	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 - Chrysophanol-9-anthrone 10V, Positive-QTOF	splash10-0006-0090000000-6fc5e2fbac7f4bf8d83b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol-9-anthrone 20V, Positive-QTOF	splash10-0006-0290000000-c63ded408e125dc8b38d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol-9-anthrone 40V, Positive-QTOF	splash10-052f-6950000000-276e5910faff689d3304	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol-9-anthrone 10V, Negative-QTOF	splash10-000i-0090000000-a28d9caa4f15bcbdeb1a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol-9-anthrone 20V, Negative-QTOF	splash10-000i-0090000000-b7e63986b8555b1920b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol-9-anthrone 40V, Negative-QTOF	splash10-000i-5690000000-d28b8b9d6e3f77ebdb89	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol-9-anthrone 10V, Positive-QTOF	splash10-0006-0090000000-250f7f03bbf18e8fd5e6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol-9-anthrone 20V, Positive-QTOF	splash10-0006-0090000000-2cead271757c14b33f3f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol-9-anthrone 40V, Positive-QTOF	splash10-0229-1890000000-f69b033b834021a6a511	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol-9-anthrone 10V, Negative-QTOF	splash10-000i-0090000000-68ba9ba0c5a355ceefe4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol-9-anthrone 20V, Negative-QTOF	splash10-000i-0090000000-68ba9ba0c5a355ceefe4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysophanol-9-anthrone 40V, Negative-QTOF	splash10-000i-0390000000-8f03babe38d2ba984541	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

3686

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Chrysophanol-9-anthrone (HMDB0250218)

MOL for HMDB0250218 (Chrysophanol-9-anthrone)

3D MOL for HMDB0250218 (Chrysophanol-9-anthrone)

3D SDF for HMDB0250218 (Chrysophanol-9-anthrone)

3D-SDF for HMDB0250218 (Chrysophanol-9-anthrone)

PDB for HMDB0250218 (Chrysophanol-9-anthrone)

3D PDB for HMDB0250218 (Chrysophanol-9-anthrone)

SMILES for HMDB0250218 (Chrysophanol-9-anthrone)

INCHI for HMDB0250218 (Chrysophanol-9-anthrone)

Structure for HMDB0250218 (Chrysophanol-9-anthrone)

3D Structure for HMDB0250218 (Chrysophanol-9-anthrone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra