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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:54:53 UTC

Update Date

2022-03-07 02:56:12 UTC

HMDB ID

HMDB0039449

Secondary Accession Numbers

HMDB39449

Metabolite Identification

Common Name

Rheinanthrone

Description

Rheinanthrone 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. Rheinanthrone has been detected, but not quantified in, green vegetables. This could make rheinanthrone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Rheinanthrone.

Structure

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

HMDB0039449
     RDKit          3D
Rheinanthrone
 30 32  0  0  0  0  0  0  0  0999 V2000
    5.4602   -0.7776   -0.3534 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5978    0.1215   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9820    1.4475   -0.0350 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1827   -0.2370   -0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7665   -1.5296   -0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4145   -1.9252   -0.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1095   -3.2428   -0.4193 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4974   -0.9063   -0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8652    0.3948    0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2184    0.7268    0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0755    1.5116    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837    1.0951    0.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4064    2.1126    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7469    1.8046    0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1842    0.5114    0.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2581   -0.5430    0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7416   -1.7896    0.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9275   -0.2040    0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9213   -1.2452   -0.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3191   -2.4197   -0.1691 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6097    1.9292    0.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4913   -2.3393   -0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3152   -3.7913   -0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5205    1.7569    0.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0685    2.2166   -0.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2101    2.0223    1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0904    3.1500    0.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4728    2.6000    0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2324    0.2455    0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4495   -2.6961   -0.0799 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  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 10  4  1  0
 18 12  1  0
 19  8  1  0
  3 21  1  0
  5 22  1  0
  7 23  1  0
 10 24  1  0
 11 25  1  0
 11 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
M  END

  Mrv0541 05061311092D          

 20 22  0  0  0  0            999 V2000
    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
    4.2868    0.8250    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
    0.7145   -0.4125    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
    2.8579    0.0000    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
    0.0000    0.0000    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
    0.7145    1.2375    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
    1.4289    0.8250    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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
   -1.4289    0.0000    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
  7  2  1  0  0  0  0
  7  4  1  0  0  0  0
  8  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  3  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 12 10  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  2  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  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
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039449

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=CC(O)=C2C(CC3=C(C(O)=CC=C3)C2=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O5/c16-10-3-1-2-7-4-8-5-9(15(19)20)6-11(17)13(8)14(18)12(7)10/h1-3,5-6,16-17H,4H2,(H,19,20)

> <INCHI_KEY>
OZFQHULMMDWMIV-UHFFFAOYSA-N

> <FORMULA>
C15H10O5

> <MOLECULAR_WEIGHT>
270.2369

> <EXACT_MASS>
270.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.559335316480173

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.54

> <JCHEM_LOGP>
3.9015993289999997

> <ALOGPS_LOGS>
-3.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.666599281509374

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5360647112237023

> <JCHEM_PKA_STRONGEST_BASIC>
-4.415365668059002

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
71.5307

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-dihydroxy-10-oxo-9H-anthracene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039449
     RDKit          3D
Rheinanthrone
 30 32  0  0  0  0  0  0  0  0999 V2000
    5.4602   -0.7776   -0.3534 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5978    0.1215   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9820    1.4475   -0.0350 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1827   -0.2370   -0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7665   -1.5296   -0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4145   -1.9252   -0.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1095   -3.2428   -0.4193 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4974   -0.9063   -0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8652    0.3948    0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2184    0.7268    0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0755    1.5116    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837    1.0951    0.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4064    2.1126    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7469    1.8046    0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1842    0.5114    0.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2581   -0.5430    0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7416   -1.7896    0.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9275   -0.2040    0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9213   -1.2452   -0.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3191   -2.4197   -0.1691 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6097    1.9292    0.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4913   -2.3393   -0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3152   -3.7913   -0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5205    1.7569    0.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0685    2.2166   -0.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2101    2.0223    1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0904    3.1500    0.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4728    2.6000    0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2324    0.2455    0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4495   -2.6961   -0.0799 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  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 10  4  1  0
 18 12  1  0
 19  8  1  0
  3 21  1  0
  5 22  1  0
  7 23  1  0
 10 24  1  0
 11 25  1  0
 11 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -0.770   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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    7                                                       
CONECT    3    1   10                                                       
CONECT    4    7    8                                                       
CONECT    5    8    9                                                       
CONECT    6    9   11                                                       
CONECT    7    2    4   12                                                  
CONECT    8    4    5   13                                                  
CONECT    9    5    6   15                                                  
CONECT   10    3   12   16                                                  
CONECT   11    6   13   17                                                  
CONECT   12    7   10   14                                                  
CONECT   13    8   11   14                                                  
CONECT   14   12   13   18                                                  
CONECT   15    9   19   20                                                  
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20   15                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0039449
HETATM    1  O1  UNL     1       5.460  -0.778  -0.353  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.598   0.121  -0.185  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.982   1.448  -0.035  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.183  -0.237  -0.149  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.766  -1.530  -0.293  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.414  -1.925  -0.265  1.00  0.00           C  
HETATM    7  O3  UNL     1       1.110  -3.243  -0.419  1.00  0.00           O  
HETATM    8  C5  UNL     1       0.497  -0.906  -0.078  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.865   0.395   0.070  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.218   0.727   0.033  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.075   1.512   0.271  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.484   1.095   0.299  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.406   2.113   0.486  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.747   1.805   0.525  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.184   0.511   0.382  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.258  -0.543   0.190  1.00  0.00           C  
HETATM   17  O4  UNL     1      -3.742  -1.790   0.056  1.00  0.00           O  
HETATM   18  C14 UNL     1      -1.927  -0.204   0.156  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.921  -1.245  -0.039  1.00  0.00           C  
HETATM   20  O5  UNL     1      -1.319  -2.420  -0.169  1.00  0.00           O  
HETATM   21  H1  UNL     1       4.610   1.929   0.786  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.491  -2.339  -0.441  1.00  0.00           H  
HETATM   23  H3  UNL     1       0.315  -3.791  -0.444  1.00  0.00           H  
HETATM   24  H4  UNL     1       2.521   1.757   0.150  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.069   2.217  -0.582  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.210   2.022   1.233  1.00  0.00           H  
HETATM   27  H7  UNL     1      -2.090   3.150   0.603  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.473   2.600   0.671  1.00  0.00           H  
HETATM   29  H9  UNL     1      -5.232   0.246   0.409  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.450  -2.696  -0.080  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   21
CONECT    4    5    5   10
CONECT    5    6   22
CONECT    6    7    8    8
CONECT    7   23
CONECT    8    9   19
CONECT    9   10   10   11
CONECT   10   24
CONECT   11   12   25   26
CONECT   12   13   13   18
CONECT   13   14   27
CONECT   14   15   15   28
CONECT   15   16   29
CONECT   16   17   18   18
CONECT   17   30
CONECT   18   19
CONECT   19   20   20
END

HMDB0039449
     RDKit          3D
Rheinanthrone
 30 32  0  0  0  0  0  0  0  0999 V2000
    5.4602   -0.7776   -0.3534 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5978    0.1215   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9820    1.4475   -0.0350 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1827   -0.2370   -0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7665   -1.5296   -0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4145   -1.9252   -0.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1095   -3.2428   -0.4193 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4974   -0.9063   -0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8652    0.3948    0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2184    0.7268    0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0755    1.5116    0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837    1.0951    0.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4064    2.1126    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7469    1.8046    0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1842    0.5114    0.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2581   -0.5430    0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7416   -1.7896    0.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9275   -0.2040    0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9213   -1.2452   -0.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3191   -2.4197   -0.1691 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6097    1.9292    0.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4913   -2.3393   -0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3152   -3.7913   -0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5205    1.7569    0.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0685    2.2166   -0.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2101    2.0223    1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0904    3.1500    0.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4728    2.6000    0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2324    0.2455    0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4495   -2.6961   -0.0799 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  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 10  4  1  0
 18 12  1  0
 19  8  1  0
  3 21  1  0
  5 22  1  0
  7 23  1  0
 10 24  1  0
 11 25  1  0
 11 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 17 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9,10-dihydro-4,5-Dihydroxy-10-oxo-2-anthroic acid, 8ci	HMDB
Rhein-9-anthrone	HMDB, MeSH
4,5-Dihydroxy-10-oxo-9,10-dihydroanthracene-2-carboxylate	Generator
Rheinanthrone	MeSH

Chemical Formula

C₁₅H₁₀O₅

Average Molecular Weight

270.2369

Monoisotopic Molecular Weight

270.05282343

IUPAC Name

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

Traditional Name

4,5-dihydroxy-10-oxo-9H-anthracene-2-carboxylic acid

CAS Registry Number

480-09-1

SMILES

OC(=O)C1=CC(O)=C2C(CC3=C(C(O)=CC=C3)C2=O)=C1

InChI Identifier

InChI=1S/C15H10O5/c16-10-3-1-2-7-4-8-5-9(15(19)20)6-11(17)13(8)14(18)12(7)10/h1-3,5-6,16-17H,4H2,(H,19,20)

InChI Key

OZFQHULMMDWMIV-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
2-naphthalenecarboxylic acid
2-naphthalenecarboxylic acid or derivatives
Hydroxybenzoic acid
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Vinylogous acid
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0039449)
Cell membrane (HMDB: HMDB0039449)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039449)

Source

Exogenous

Exogenous (HMDB: HMDB0039449)

Food

Food (HMDB: HMDB0039449)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0039449)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0039449)

Biological role

Nutrient (HMDB: HMDB0039449)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	250 - 280 °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	2.54	ALOGPS
logP	3.9	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.54	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.53 m³·mol⁻¹	ChemAxon
Polarizability	26.56 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	161.165	31661259
DarkChem	[M-H]-	163.68	31661259
DeepCCS	[M+H]+	168.438	30932474
DeepCCS	[M-H]-	166.079	30932474
DeepCCS	[M-2H]-	198.965	30932474
DeepCCS	[M+Na]+	174.531	30932474
AllCCS	[M+H]+	160.0	32859911
AllCCS	[M+H-H2O]+	156.2	32859911
AllCCS	[M+NH4]+	163.5	32859911
AllCCS	[M+Na]+	164.5	32859911
AllCCS	[M-H]-	160.9	32859911
AllCCS	[M+Na-2H]-	160.1	32859911
AllCCS	[M+HCOO]-	159.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rheinanthrone	OC(=O)C1=CC(O)=C2C(CC3=C(C(O)=CC=C3)C2=O)=C1	4099.3	Standard polar	33892256
Rheinanthrone	OC(=O)C1=CC(O)=C2C(CC3=C(C(O)=CC=C3)C2=O)=C1	2344.2	Standard non polar	33892256
Rheinanthrone	OC(=O)C1=CC(O)=C2C(CC3=C(C(O)=CC=C3)C2=O)=C1	2597.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Rheinanthrone,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O)=C2C(=O)C3=C(O)C=CC=C3CC2=C1	2748.2	Semi standard non polar	33892256
Rheinanthrone,1TMS,isomer #2	C[Si](C)(C)OC1=CC(C(=O)O)=CC2=C1C(=O)C1=C(O)C=CC=C1C2	2695.3	Semi standard non polar	33892256
Rheinanthrone,1TMS,isomer #3	C[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O)C=C(C(=O)O)C=C1C2	2726.6	Semi standard non polar	33892256
Rheinanthrone,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC2=C(C(=O)C3=C(O)C=CC=C3C2)C(O[Si](C)(C)C)=C1	2686.7	Semi standard non polar	33892256
Rheinanthrone,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=CC=C3CC2=C1	2715.5	Semi standard non polar	33892256
Rheinanthrone,2TMS,isomer #3	C[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(C=C(C(=O)O)C=C1O[Si](C)(C)C)C2	2702.8	Semi standard non polar	33892256
Rheinanthrone,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC2=C(C(=O)C3=C(C=CC=C3O[Si](C)(C)C)C2)C(O[Si](C)(C)C)=C1	2694.8	Semi standard non polar	33892256
Rheinanthrone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=C2C(=O)C3=C(O)C=CC=C3CC2=C1	2990.0	Semi standard non polar	33892256
Rheinanthrone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(C(=O)O)=CC2=C1C(=O)C1=C(O)C=CC=C1C2	2942.9	Semi standard non polar	33892256
Rheinanthrone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O)C=C(C(=O)O)C=C1C2	2970.6	Semi standard non polar	33892256
Rheinanthrone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=C(C(=O)C3=C(O)C=CC=C3C2)C(O[Si](C)(C)C(C)(C)C)=C1	3141.9	Semi standard non polar	33892256
Rheinanthrone,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=C3CC2=C1	3193.6	Semi standard non polar	33892256
Rheinanthrone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(C=C(C(=O)O)C=C1O[Si](C)(C)C(C)(C)C)C2	3189.5	Semi standard non polar	33892256
Rheinanthrone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=C(C(=O)C3=C(C=CC=C3O[Si](C)(C)C(C)(C)C)C2)C(O[Si](C)(C)C(C)(C)C)=C1	3339.6	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 - Rheinanthrone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fdo-0290000000-3a884ca2c0a98b691ac6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rheinanthrone GC-MS (3 TMS) - 70eV, Positive	splash10-00dj-9217800000-05220cff64af7b1f7557	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rheinanthrone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rheinanthrone 10V, Positive-QTOF	splash10-00di-0090000000-01f5fad042a50121726a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rheinanthrone 20V, Positive-QTOF	splash10-00b9-0090000000-12f94b77182920b5633f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rheinanthrone 40V, Positive-QTOF	splash10-004i-1390000000-4beec551f3f29fc78435	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rheinanthrone 10V, Negative-QTOF	splash10-014i-0090000000-f68e824c5c0604bd0ea6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rheinanthrone 20V, Negative-QTOF	splash10-00or-0090000000-23cc19dfab272e589358	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rheinanthrone 40V, Negative-QTOF	splash10-004l-3590000000-fee1fca65e457081a529	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rheinanthrone 10V, Negative-QTOF	splash10-004i-0090000000-6929adb4eb50cc47a297	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rheinanthrone 20V, Negative-QTOF	splash10-004i-0090000000-6929adb4eb50cc47a297	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rheinanthrone 40V, Negative-QTOF	splash10-002b-0940000000-c9a5482ce0432070ad43	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rheinanthrone 10V, Positive-QTOF	splash10-00di-0090000000-6cf28d3e8e6f4d9278aa	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rheinanthrone 20V, Positive-QTOF	splash10-0uk9-0090000000-7889a5b6d1fbc74444ab	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rheinanthrone 40V, Positive-QTOF	splash10-0zfr-0790000000-d9742dd34ca6b9b3526a	2021-09-25	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

DB13175

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB019048

KNApSAcK ID

C00054854

Chemspider ID

106641

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119396

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Rheinanthrone (HMDB0039449)

MOL for HMDB0039449 (Rheinanthrone)

3D MOL for HMDB0039449 (Rheinanthrone)

3D SDF for HMDB0039449 (Rheinanthrone)

3D-SDF for HMDB0039449 (Rheinanthrone)

PDB for HMDB0039449 (Rheinanthrone)

3D PDB for HMDB0039449 (Rheinanthrone)

SMILES for HMDB0039449 (Rheinanthrone)

INCHI for HMDB0039449 (Rheinanthrone)

Structure for HMDB0039449 (Rheinanthrone)

3D Structure for HMDB0039449 (Rheinanthrone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra