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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:17:20 UTC

Update Date

2022-03-07 02:54:06 UTC

HMDB ID

HMDB0034444

Secondary Accession Numbers

HMDB34444

Metabolite Identification

Common Name

Citreorosein

Description

Citreorosein belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. Thus, citreorosein is considered to be an aromatic polyketide. Citreorosein has been detected, but not quantified in, green vegetables. This could make citreorosein a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Citreorosein.

Structure

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

HMDB0034444
     RDKit          3D
Citreorosein
 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.2337    2.6681    0.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559    1.4092   -0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6640    0.7965   -0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8054    1.5758   -0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0589    1.0451   -0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2015    1.8290   -0.3861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2027   -0.3066   -0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0542   -1.1396   -0.5588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2589   -2.4758   -0.7130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7938   -0.5919   -0.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5944   -1.4142   -0.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811   -2.6342   -0.5614 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7407   -0.8297   -0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8488   -1.6553   -0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8260   -3.0143   -0.4377 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0951   -1.0066   -0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1614    0.3500    0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0037    0.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7640    1.0288    1.5472 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0534    1.1434    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8267    0.5350   -0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6877    2.6451   -0.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7091    2.0524    0.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1648   -0.7955   -0.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6714   -3.2317   -0.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1907   -3.7090   -0.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0116   -1.5863   -0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5098    2.0242   -0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3111    0.3675   -0.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1838    1.6934    2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1066    2.2238    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  2  0
 21  2  1  0
 10  3  1  0
 21 13  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 15 26  1  0
 16 27  1  0
 18 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
M  END


  Mrv0541 05061307492D          

 21 23  0  0  0  0            999 V2000
    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
    5.7158    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
    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
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   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
  6  1  2  0  0  0  0
  6  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  1  1  0  0  0  0
  9  3  1  0  0  0  0
 10  2  2  0  0  0  0
 11  4  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  5  1  0  0  0  0
 17  7  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20 14  2  0  0  0  0
 21 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034444

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(O)C=C1O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O6/c16-5-6-1-8-12(10(18)2-6)15(21)13-9(14(8)20)3-7(17)4-11(13)19/h1-4,16-19H,5H2

> <INCHI_KEY>
YQHZABGPIPECSQ-UHFFFAOYSA-N

> <FORMULA>
C15H10O6

> <MOLECULAR_WEIGHT>
286.2363

> <EXACT_MASS>
286.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
27.575050316587244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3,8-trihydroxy-6-(hydroxymethyl)-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
2.540660342333333

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.22099744835048

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.3823511771412145

> <JCHEM_PKA_STRONGEST_BASIC>
-2.945292474132076

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
73.9096

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,8-trihydroxy-6-(hydroxymethyl)anthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034444
     RDKit          3D
Citreorosein
 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.2337    2.6681    0.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559    1.4092   -0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6640    0.7965   -0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8054    1.5758   -0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0589    1.0451   -0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2015    1.8290   -0.3861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2027   -0.3066   -0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0542   -1.1396   -0.5588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2589   -2.4758   -0.7130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7938   -0.5919   -0.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5944   -1.4142   -0.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811   -2.6342   -0.5614 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7407   -0.8297   -0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8488   -1.6553   -0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8260   -3.0143   -0.4377 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0951   -1.0066   -0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1614    0.3500    0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0037    0.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7640    1.0288    1.5472 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0534    1.1434    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8267    0.5350   -0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6877    2.6451   -0.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7091    2.0524    0.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1648   -0.7955   -0.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6714   -3.2317   -0.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1907   -3.7090   -0.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0116   -1.5863   -0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5098    2.0242   -0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3111    0.3675   -0.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1838    1.6934    2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1066    2.2238    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  2  0
 21  2  1  0
 10  3  1  0
 21 13  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 15 26  1  0
 16 27  1  0
 18 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  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   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       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      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
CONECT    1    6    8                                                       
CONECT    2    6   10                                                       
CONECT    3    7    9                                                       
CONECT    4    7   11                                                       
CONECT    5    6   16                                                       
CONECT    6    1    2    5                                                  
CONECT    7    3    4   17                                                  
CONECT    8    1   12   14                                                  
CONECT    9    3   13   14                                                  
CONECT   10    2   12   18                                                  
CONECT   11    4   13   19                                                  
CONECT   12    8   10   15                                                  
CONECT   13    9   11   15                                                  
CONECT   14    8    9   20                                                  
CONECT   15   12   13   21                                                  
CONECT   16    5                                                            
CONECT   17    7                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   14                                                            
CONECT   21   15                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0034444
HETATM    1  O1  UNL     1      -0.234   2.668   0.027  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.356   1.409  -0.114  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.664   0.796  -0.264  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.805   1.576  -0.256  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.059   1.045  -0.394  1.00  0.00           C  
HETATM    6  O2  UNL     1      -5.202   1.829  -0.386  1.00  0.00           O  
HETATM    7  C5  UNL     1      -4.203  -0.307  -0.546  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.054  -1.140  -0.559  1.00  0.00           C  
HETATM    9  O3  UNL     1      -3.259  -2.476  -0.713  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.794  -0.592  -0.419  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.594  -1.414  -0.427  1.00  0.00           C  
HETATM   12  O4  UNL     1      -0.681  -2.634  -0.561  1.00  0.00           O  
HETATM   13  C9  UNL     1       0.741  -0.830  -0.278  1.00  0.00           C  
HETATM   14  C10 UNL     1       1.849  -1.655  -0.293  1.00  0.00           C  
HETATM   15  O5  UNL     1       1.826  -3.014  -0.438  1.00  0.00           O  
HETATM   16  C11 UNL     1       3.095  -1.007  -0.143  1.00  0.00           C  
HETATM   17  C12 UNL     1       3.161   0.350   0.004  1.00  0.00           C  
HETATM   18  C13 UNL     1       4.508   1.004   0.161  1.00  0.00           C  
HETATM   19  O6  UNL     1       4.764   1.029   1.547  1.00  0.00           O  
HETATM   20  C14 UNL     1       2.053   1.143   0.015  1.00  0.00           C  
HETATM   21  C15 UNL     1       0.827   0.535  -0.129  1.00  0.00           C  
HETATM   22  H1  UNL     1      -2.688   2.645  -0.136  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.709   2.052   0.448  1.00  0.00           H  
HETATM   24  H3  UNL     1      -5.165  -0.796  -0.660  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.671  -3.232  -0.754  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.191  -3.709  -0.552  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.012  -1.586  -0.144  1.00  0.00           H  
HETATM   28  H7  UNL     1       4.510   2.024  -0.269  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.311   0.367  -0.278  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.184   1.693   2.001  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.107   2.224   0.133  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4    4   10
CONECT    4    5   22
CONECT    5    6    7    7
CONECT    6   23
CONECT    7    8   24
CONECT    8    9   10   10
CONECT    9   25
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   14   21
CONECT   14   15   16
CONECT   15   26
CONECT   16   17   17   27
CONECT   17   18   20
CONECT   18   19   28   29
CONECT   19   30
CONECT   20   21   21   31
END

HMDB0034444
     RDKit          3D
Citreorosein
 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.2337    2.6681    0.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559    1.4092   -0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6640    0.7965   -0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8054    1.5758   -0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0589    1.0451   -0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2015    1.8290   -0.3861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2027   -0.3066   -0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0542   -1.1396   -0.5588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2589   -2.4758   -0.7130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7938   -0.5919   -0.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5944   -1.4142   -0.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811   -2.6342   -0.5614 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7407   -0.8297   -0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8488   -1.6553   -0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8260   -3.0143   -0.4377 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0951   -1.0066   -0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1614    0.3500    0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0037    0.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7640    1.0288    1.5472 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0534    1.1434    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8267    0.5350   -0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6877    2.6451   -0.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7091    2.0524    0.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1648   -0.7955   -0.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6714   -3.2317   -0.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1907   -3.7090   -0.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0116   -1.5863   -0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5098    2.0242   -0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3111    0.3675   -0.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1838    1.6934    2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1066    2.2238    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  2  0
 21  2  1  0
 10  3  1  0
 21 13  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 15 26  1  0
 16 27  1  0
 18 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Omega-hydroxyemodin	Kegg
.omega.-hydroxyemodin	HMDB
1,3,8-Trihydroxy-6-(hydroxymethyl)-9,10-anthracenedione	HMDB
1,3,8-Trihydroxy-6-(hydroxymethyl)anthra-9,10-quinone	HMDB
W-Hydroxyemodin	HMDB
1,3,8-Trihydroxy-6-hydroxymethylanthraquinone	MeSH

Chemical Formula

C₁₅H₁₀O₆

Average Molecular Weight

286.2363

Monoisotopic Molecular Weight

286.047738052

IUPAC Name

1,3,8-trihydroxy-6-(hydroxymethyl)-9,10-dihydroanthracene-9,10-dione

Traditional Name

1,3,8-trihydroxy-6-(hydroxymethyl)anthracene-9,10-dione

CAS Registry Number

481-73-2

SMILES

OCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(O)C=C1O)C2=O

InChI Identifier

InChI=1S/C15H10O6/c16-5-6-1-8-12(10(18)2-6)15(21)13-9(14(8)20)3-7(17)4-11(13)19/h1-4,16-19H,5H2

InChI Key

YQHZABGPIPECSQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

hydroxyanthraquinones (CHEBI:81348 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034444)
Cytoplasm (HMDB: HMDB0034444)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034444)

Source

Exogenous

Food

Food (HMDB: HMDB0034444)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0034444)

Not Available

Nutrient (HMDB: HMDB0034444)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	288 °C	Not Available
Boiling Point	672.30 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	95.38 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.380 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.37 g/L	ALOGPS
logP	2.02	ALOGPS
logP	2.54	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.38	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.91 m³·mol⁻¹	ChemAxon
Polarizability	27.58 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]+	166.988	31661259
DarkChem	[M-H]-	167.131	31661259
DeepCCS	[M+H]+	166.053	30932474
DeepCCS	[M-H]-	163.695	30932474
DeepCCS	[M-2H]-	197.31	30932474
DeepCCS	[M+Na]+	172.537	30932474
AllCCS	[M+H]+	163.6	32859911
AllCCS	[M+H-H2O]+	160.0	32859911
AllCCS	[M+NH4]+	167.0	32859911
AllCCS	[M+Na]+	167.9	32859911
AllCCS	[M-H]-	164.0	32859911
AllCCS	[M+Na-2H]-	163.4	32859911
AllCCS	[M+HCOO]-	162.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citreorosein	OCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(O)C=C1O)C2=O	4255.8	Standard polar	33892256
Citreorosein	OCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(O)C=C1O)C2=O	2666.4	Standard non polar	33892256
Citreorosein	OCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(O)C=C1O)C2=O	3022.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Citreorosein,1TMS,isomer #1	C[Si](C)(C)OCC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C=C3C(=O)C2=C1	2874.4	Semi standard non polar	33892256
Citreorosein,1TMS,isomer #2	C[Si](C)(C)OC1=CC(CO)=CC2=C1C(=O)C1=C(O)C=C(O)C=C1C2=O	2834.3	Semi standard non polar	33892256
Citreorosein,1TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C2C(=O)C3=C(O)C=C(CO)C=C3C(=O)C2=C1	2897.1	Semi standard non polar	33892256
Citreorosein,1TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C1=C(O)C=C(CO)C=C1C2=O	2846.8	Semi standard non polar	33892256
Citreorosein,2TMS,isomer #1	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O)C=C(O)C=C3C(=O)C2=C1	2821.3	Semi standard non polar	33892256
Citreorosein,2TMS,isomer #2	C[Si](C)(C)OCC1=CC(O)=C2C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3C(=O)C2=C1	2880.2	Semi standard non polar	33892256
Citreorosein,2TMS,isomer #3	C[Si](C)(C)OCC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3C(=O)C2=C1	2825.2	Semi standard non polar	33892256
Citreorosein,2TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(CO)C=C1C2=O	2786.4	Semi standard non polar	33892256
Citreorosein,2TMS,isomer #5	C[Si](C)(C)OC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(CO)C=C3C(=O)C2=C1	2799.3	Semi standard non polar	33892256
Citreorosein,2TMS,isomer #6	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O)C=C(CO)C=C3C(=O)C2=C1	2803.7	Semi standard non polar	33892256
Citreorosein,3TMS,isomer #1	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3C(=O)C2=C1	2818.1	Semi standard non polar	33892256
Citreorosein,3TMS,isomer #2	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3C(=O)C2=C1	2813.6	Semi standard non polar	33892256
Citreorosein,3TMS,isomer #3	C[Si](C)(C)OCC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3C(=O)C2=C1	2815.2	Semi standard non polar	33892256
Citreorosein,3TMS,isomer #4	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(CO)C=C3C(=O)C2=C1	2789.9	Semi standard non polar	33892256
Citreorosein,4TMS,isomer #1	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3C(=O)C2=C1	2828.6	Semi standard non polar	33892256
Citreorosein,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C=C3C(=O)C2=C1	3140.9	Semi standard non polar	33892256
Citreorosein,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(CO)=CC2=C1C(=O)C1=C(O)C=C(O)C=C1C2=O	3089.8	Semi standard non polar	33892256
Citreorosein,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C3=C(O)C=C(CO)C=C3C(=O)C2=C1	3149.2	Semi standard non polar	33892256
Citreorosein,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C1=C(O)C=C(CO)C=C1C2=O	3103.4	Semi standard non polar	33892256
Citreorosein,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O)C=C(O)C=C3C(=O)C2=C1	3308.7	Semi standard non polar	33892256
Citreorosein,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1=CC(O)=C2C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	3378.1	Semi standard non polar	33892256
Citreorosein,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3C(=O)C2=C1	3314.3	Semi standard non polar	33892256
Citreorosein,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(CO)C=C1C2=O	3292.4	Semi standard non polar	33892256
Citreorosein,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(CO)C=C3C(=O)C2=C1	3303.9	Semi standard non polar	33892256
Citreorosein,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O)C=C(CO)C=C3C(=O)C2=C1	3298.9	Semi standard non polar	33892256
Citreorosein,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	3512.3	Semi standard non polar	33892256
Citreorosein,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3C(=O)C2=C1	3493.4	Semi standard non polar	33892256
Citreorosein,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	3501.3	Semi standard non polar	33892256
Citreorosein,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(CO)C=C3C(=O)C2=C1	3484.6	Semi standard non polar	33892256
Citreorosein,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3C(=O)C2=C1	3687.8	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 - Citreorosein GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0490000000-8482777666d2c2415021	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citreorosein GC-MS (4 TMS) - 70eV, Positive	splash10-0rta-4140190000-a41c270b7f5d039affed	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citreorosein GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citreorosein 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 - Citreorosein 10V, Positive-QTOF	splash10-000i-0090000000-9b6f47bcfac51b97493e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreorosein 20V, Positive-QTOF	splash10-000i-0690000000-a5c1f770a8c40bfa34a8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreorosein 40V, Positive-QTOF	splash10-014r-3390000000-32b84b7feb810bd7bd9e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreorosein 10V, Negative-QTOF	splash10-000i-0090000000-2170f0e2a658090be48a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreorosein 20V, Negative-QTOF	splash10-052r-0090000000-e9efed7f613c099a442f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreorosein 40V, Negative-QTOF	splash10-052o-4490000000-a1ad4c1755a54d0c44fa	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreorosein 10V, Positive-QTOF	splash10-00kr-0090000000-1a081b643629af6eb194	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreorosein 20V, Positive-QTOF	splash10-000i-0090000000-bebe353f3ef7723b939d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreorosein 40V, Positive-QTOF	splash10-0uxr-0690000000-f1b819701f7cc496ba76	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreorosein 10V, Negative-QTOF	splash10-000i-0090000000-3713e1ac18e8a67ad454	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreorosein 20V, Negative-QTOF	splash10-000i-0090000000-f9045d2c916d668e8e34	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citreorosein 40V, Negative-QTOF	splash10-06tr-0190000000-f09a18084abfcacf42de	2021-09-22	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

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

Citreorosein

METLIN ID

Not Available

PubChem Compound

361512

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1534991

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 Citreorosein (HMDB0034444)

MOL for HMDB0034444 (Citreorosein)

3D MOL for HMDB0034444 (Citreorosein)

3D SDF for HMDB0034444 (Citreorosein)

3D-SDF for HMDB0034444 (Citreorosein)

PDB for HMDB0034444 (Citreorosein)

3D PDB for HMDB0034444 (Citreorosein)

SMILES for HMDB0034444 (Citreorosein)

INCHI for HMDB0034444 (Citreorosein)

Structure for HMDB0034444 (Citreorosein)

3D Structure for HMDB0034444 (Citreorosein)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra