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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:35:57 UTC

Update Date

2022-03-07 02:54:56 UTC

HMDB ID

HMDB0036457

Secondary Accession Numbers

HMDB36457

Metabolite Identification

Common Name

Emodinanthranol

Description

Emodinanthranol, also known as emodin-9-anthrone, belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings. Emodinanthranol has been detected, but not quantified in, several different foods, such as garden rhubarbs (Rheum rhabarbarum), green tea, alcoholic beverages, herbal tea, and red tea. This could make emodinanthranol a potential biomarker for the consumption of these foods. Emodinanthranol 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 Emodinanthranol.

Structure

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

HMDB0036457
     RDKit          3D
Emodinanthranol
 31 33  0  0  0  0  0  0  0  0999 V2000
   -4.6650    0.8277   -0.9533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3539    0.3517   -0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2905   -0.6517    0.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0862   -1.0951    1.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9968   -2.0816    1.9814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9028   -0.5516    0.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9461    0.4344   -0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1807    0.8847   -0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2629    1.0643   -0.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5344    0.5488   -0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7434    1.0826   -0.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667    0.6659   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1650    1.2041   -0.9105 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0517   -0.3144    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8753   -0.8538    0.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8936   -1.8563    1.9657 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6390   -0.4343    0.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3940   -1.0037    1.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4499   -1.9046    1.9111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4476    0.1145   -0.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8799    1.8516   -0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6121    0.8151   -2.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2315   -1.0717    0.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7943   -2.5411    2.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2298    1.6619   -1.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032    2.1744   -0.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3004    0.8821   -2.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7189    1.8596   -1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6380    0.7960   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9938   -0.6813    0.9124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7870   -2.1782    2.3152 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  1  0
 12 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 10  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
  9 26  1  0
  9 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
M  END


  Mrv0541 01081307472D          

 19 21  0  0  0  0            999 V2000
   -3.6929   -2.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4073   -2.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4073   -3.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6929   -4.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9784   -3.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9784   -2.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6929   -4.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9784   -5.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2639   -4.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2639   -4.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9784   -6.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2639   -6.5215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495   -6.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495   -5.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1218   -2.3964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2639   -2.3964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495   -3.6340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8350   -4.8715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2639   -7.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  2  0  0  0  0
  9  8  1  0  0  0  0
  8 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  2 15  1  0  0  0  0
  6 16  1  0  0  0  0
 10 17  2  0  0  0  0
 14 18  1  0  0  0  0
 12 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036457

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C=C3CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O4/c1-7-2-8-4-9-5-10(16)6-12(18)14(9)15(19)13(8)11(17)3-7/h2-3,5-6,16-18H,4H2,1H3

> <INCHI_KEY>
LAJSXCAVRQXZIO-UHFFFAOYSA-N

> <FORMULA>
C15H12O4

> <MOLECULAR_WEIGHT>
256.2534

> <EXACT_MASS>
256.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.50717669234175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3,8-trihydroxy-6-methyl-9,10-dihydroanthracen-9-one

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
4.453872488666667

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.01257303837639

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.965975537429991

> <JCHEM_PKA_STRONGEST_BASIC>
-4.128043918413479

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
71.2966

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.65e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,8-trihydroxy-6-methyl-10H-anthracen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036457
     RDKit          3D
Emodinanthranol
 31 33  0  0  0  0  0  0  0  0999 V2000
   -4.6650    0.8277   -0.9533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3539    0.3517   -0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2905   -0.6517    0.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0862   -1.0951    1.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9968   -2.0816    1.9814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9028   -0.5516    0.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9461    0.4344   -0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1807    0.8847   -0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2629    1.0643   -0.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5344    0.5488   -0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7434    1.0826   -0.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667    0.6659   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1650    1.2041   -0.9105 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0517   -0.3144    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8753   -0.8538    0.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8936   -1.8563    1.9657 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6390   -0.4343    0.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3940   -1.0037    1.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4499   -1.9046    1.9111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4476    0.1145   -0.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8799    1.8516   -0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6121    0.8151   -2.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2315   -1.0717    0.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7943   -2.5411    2.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2298    1.6619   -1.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032    2.1744   -0.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3004    0.8821   -2.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7189    1.8596   -1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6380    0.7960   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9938   -0.6813    0.9124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7870   -2.1782    2.3152 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  1  0
 12 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 10  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
  9 26  1  0
  9 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
M  END

HEADER    PROTEIN                                 08-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-JAN-13         0                                  
HETATM    1  C   UNK     0      -6.893  -4.473   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.227  -5.243   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.227  -6.783   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.893  -7.553   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.560  -6.783   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.560  -5.243   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.893  -9.093   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.560  -9.863   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.226  -9.093   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.226  -7.553   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.560 -11.403   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.226 -12.173   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.892 -11.403   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.892  -9.863   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -9.561  -4.473   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -4.226  -4.473   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.892  -6.783   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.559  -9.093   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.226 -13.713   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    6   10    4                                                  
CONECT    6    5    1   16                                                  
CONECT    7    4    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9   10   14    8                                                  
CONECT   10    5    9   17                                                  
CONECT   11    8   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14    9   13   18                                                  
CONECT   15    2                                                            
CONECT   16    6                                                            
CONECT   17   10                                                            
CONECT   18   14                                                            
CONECT   19   12                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0036457
HETATM    1  C1  UNL     1      -4.665   0.828  -0.953  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.354   0.352  -0.437  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.290  -0.652   0.540  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.086  -1.095   1.020  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.997  -2.082   1.981  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.903  -0.552   0.542  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.946   0.434  -0.417  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.181   0.885  -0.905  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.263   1.064  -0.978  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.534   0.549  -0.425  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.743   1.083  -0.893  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.967   0.666  -0.438  1.00  0.00           C  
HETATM   13  O2  UNL     1       5.165   1.204  -0.910  1.00  0.00           O  
HETATM   14  C12 UNL     1       4.052  -0.314   0.517  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.875  -0.854   0.992  1.00  0.00           C  
HETATM   16  O3  UNL     1       2.894  -1.856   1.966  1.00  0.00           O  
HETATM   17  C14 UNL     1       1.639  -0.434   0.533  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.394  -1.004   1.034  1.00  0.00           C  
HETATM   19  O4  UNL     1       0.450  -1.905   1.911  1.00  0.00           O  
HETATM   20  H1  UNL     1      -5.448   0.114  -0.586  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.880   1.852  -0.580  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.612   0.815  -2.067  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.232  -1.072   0.908  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.794  -2.541   2.394  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.230   1.662  -1.662  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.203   2.174  -0.866  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.300   0.882  -2.086  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.719   1.860  -1.648  1.00  0.00           H  
HETATM   29  H10 UNL     1       5.638   0.796  -1.714  1.00  0.00           H  
HETATM   30  H11 UNL     1       4.994  -0.681   0.912  1.00  0.00           H  
HETATM   31  H12 UNL     1       3.787  -2.178   2.315  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   26   27
CONECT   10   11   11   17
CONECT   11   12   28
CONECT   12   13   14   14
CONECT   13   29
CONECT   14   15   30
CONECT   15   16   17   17
CONECT   16   31
CONECT   17   18
CONECT   18   19   19
END

HMDB0036457
     RDKit          3D
Emodinanthranol
 31 33  0  0  0  0  0  0  0  0999 V2000
   -4.6650    0.8277   -0.9533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3539    0.3517   -0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2905   -0.6517    0.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0862   -1.0951    1.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9968   -2.0816    1.9814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9028   -0.5516    0.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9461    0.4344   -0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1807    0.8847   -0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2629    1.0643   -0.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5344    0.5488   -0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7434    1.0826   -0.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667    0.6659   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1650    1.2041   -0.9105 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0517   -0.3144    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8753   -0.8538    0.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8936   -1.8563    1.9657 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6390   -0.4343    0.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3940   -1.0037    1.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4499   -1.9046    1.9111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4476    0.1145   -0.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8799    1.8516   -0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6121    0.8151   -2.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2315   -1.0717    0.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7943   -2.5411    2.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2298    1.6619   -1.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032    2.1744   -0.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3004    0.8821   -2.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7189    1.8596   -1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6380    0.7960   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9938   -0.6813    0.9124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7870   -2.1782    2.3152 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  1  0
 12 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 10  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
  9 26  1  0
  9 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,3,8-Trihydroxy-6-methylanthrone	ChEBI
Emodin-9-anthrone	ChEBI
Emodinanthrone	ChEBI
1,3,8-Trihydroxy-6-methyl-9(10H)-anthracenone	HMDB
1,6,8-Trihydroxy-3-methyl-10-hydroanthracen-9-one	HMDB
6-Methyl-1,3,8,9-anthracenetetrol	HMDB
Emodin anthrone	HMDB
Emodinol	HMDB
Frangula emodin anthrone	HMDB
Frangulaemodinanthranol	HMDB
Frangulaemodinanthrone	HMDB
Protophyscihydrone	HMDB

Chemical Formula

C₁₅H₁₂O₄

Average Molecular Weight

256.2534

Monoisotopic Molecular Weight

256.073558872

IUPAC Name

1,3,8-trihydroxy-6-methyl-9,10-dihydroanthracen-9-one

Traditional Name

1,3,8-trihydroxy-6-methyl-10H-anthracen-9-one

CAS Registry Number

491-60-1

SMILES

CC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C=C3CC2=C1

InChI Identifier

InChI=1S/C15H12O4/c1-7-2-8-4-9-5-10(16)6-12(18)14(9)15(19)13(8)11(17)3-7/h2-3,5-6,16-18H,4H2,1H3

InChI Key

LAJSXCAVRQXZIO-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
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

a hydroxyanthraquinone (CPD-9557 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036457)

Cellular substructure

Membrane (HMDB: HMDB0036457)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036457)

Source

Exogenous

Food

Food (HMDB: HMDB0036457)

Vegetable

Stalk vegetable

Garden rhubarb (FooDB: FOOD00154)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0036457)

Not Available

Nutrient (HMDB: HMDB0036457)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	250 - 258 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.98 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	2.55	ALOGPS
logP	4.45	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	7.97	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.3 m³·mol⁻¹	ChemAxon
Polarizability	26.51 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]+	159.191	31661259
DarkChem	[M-H]-	159.517	31661259
DeepCCS	[M+H]+	161.231	30932474
DeepCCS	[M-H]-	158.874	30932474
DeepCCS	[M-2H]-	191.759	30932474
DeepCCS	[M+Na]+	167.325	30932474
AllCCS	[M+H]+	156.7	32859911
AllCCS	[M+H-H2O]+	152.8	32859911
AllCCS	[M+NH4]+	160.3	32859911
AllCCS	[M+Na]+	161.4	32859911
AllCCS	[M-H]-	159.0	32859911
AllCCS	[M+Na-2H]-	158.2	32859911
AllCCS	[M+HCOO]-	157.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Emodinanthranol	CC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C=C3CC2=C1	3971.9	Standard polar	33892256
Emodinanthranol	CC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C=C3CC2=C1	2393.4	Standard non polar	33892256
Emodinanthranol	CC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C=C3CC2=C1	2700.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Emodinanthranol,1TMS,isomer #1	CC1=CC2=C(C(=O)C3=C(O)C=C(O)C=C3C2)C(O[Si](C)(C)C)=C1	2515.2	Semi standard non polar	33892256
Emodinanthranol,1TMS,isomer #2	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3CC2=C1	2534.2	Semi standard non polar	33892256
Emodinanthranol,1TMS,isomer #3	CC1=CC(O)=C2C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3CC2=C1	2614.1	Semi standard non polar	33892256
Emodinanthranol,2TMS,isomer #1	CC1=CC2=C(C(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C)C2)C(O[Si](C)(C)C)=C1	2491.2	Semi standard non polar	33892256
Emodinanthranol,2TMS,isomer #2	CC1=CC2=C(C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3C2)C(O[Si](C)(C)C)=C1	2539.8	Semi standard non polar	33892256
Emodinanthranol,2TMS,isomer #3	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3CC2=C1	2550.2	Semi standard non polar	33892256
Emodinanthranol,3TMS,isomer #1	CC1=CC2=C(C(=O)C3=C(C=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C2)C(O[Si](C)(C)C)=C1	2527.4	Semi standard non polar	33892256
Emodinanthranol,1TBDMS,isomer #1	CC1=CC2=C(C(=O)C3=C(O)C=C(O)C=C3C2)C(O[Si](C)(C)C(C)(C)C)=C1	2777.7	Semi standard non polar	33892256
Emodinanthranol,1TBDMS,isomer #2	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3CC2=C1	2793.2	Semi standard non polar	33892256
Emodinanthranol,1TBDMS,isomer #3	CC1=CC(O)=C2C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3CC2=C1	2853.8	Semi standard non polar	33892256
Emodinanthranol,2TBDMS,isomer #1	CC1=CC2=C(C(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)C2)C(O[Si](C)(C)C(C)(C)C)=C1	2951.0	Semi standard non polar	33892256
Emodinanthranol,2TBDMS,isomer #2	CC1=CC2=C(C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3C2)C(O[Si](C)(C)C(C)(C)C)=C1	2991.1	Semi standard non polar	33892256
Emodinanthranol,2TBDMS,isomer #3	CC1=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=C3CC2=C1	3006.7	Semi standard non polar	33892256
Emodinanthranol,3TBDMS,isomer #1	CC1=CC2=C(C(=O)C3=C(C=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C2)C(O[Si](C)(C)C(C)(C)C)=C1	3177.3	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 - Emodinanthranol GC-MS (Non-derivatized) - 70eV, Positive	splash10-06vi-0490000000-3844c5587cf9ac8d9d77	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Emodinanthranol GC-MS (3 TMS) - 70eV, Positive	splash10-0a4i-3416900000-59eff0fd88e587be6b12	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Emodinanthranol 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 - Emodinanthranol 10V, Negative-QTOF	splash10-0a4i-0090000000-0e95958fee1b3636638f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emodinanthranol 20V, Negative-QTOF	splash10-0a4i-0090000000-b4c5436689f642a04dae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emodinanthranol 40V, Negative-QTOF	splash10-0btc-4490000000-2dfcad46e64d13e876d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emodinanthranol 10V, Negative-QTOF	splash10-0a4i-0090000000-82e226df9342cd67d796	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emodinanthranol 20V, Negative-QTOF	splash10-0a4i-0090000000-82e226df9342cd67d796	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emodinanthranol 40V, Negative-QTOF	splash10-0c00-0390000000-dc620c507710a2e8fc8f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emodinanthranol 10V, Positive-QTOF	splash10-0a4i-0090000000-34be4117595323691e56	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emodinanthranol 20V, Positive-QTOF	splash10-0a4i-0290000000-65bf1bc9c8af7509bcb0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emodinanthranol 40V, Positive-QTOF	splash10-0ap0-4970000000-e316817877a6dcba7058	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emodinanthranol 10V, Positive-QTOF	splash10-0a4i-0090000000-b46e3a63d530434294a2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emodinanthranol 20V, Positive-QTOF	splash10-0a4i-0090000000-c413cebb2f7c69ce4ba4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emodinanthranol 40V, Positive-QTOF	splash10-00bi-1790000000-eb54bd90c1ad1df4714d	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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

FDB015346

KNApSAcK ID

C00000569

Chemspider ID

109339

KEGG Compound ID

Not Available

BioCyc ID

RXN-14896

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122635

PDB ID

Not Available

ChEBI ID

150013

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1855301

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 Emodinanthranol (HMDB0036457)

MOL for HMDB0036457 (Emodinanthranol)

3D MOL for HMDB0036457 (Emodinanthranol)

3D SDF for HMDB0036457 (Emodinanthranol)

3D-SDF for HMDB0036457 (Emodinanthranol)

PDB for HMDB0036457 (Emodinanthranol)

3D PDB for HMDB0036457 (Emodinanthranol)

SMILES for HMDB0036457 (Emodinanthranol)

INCHI for HMDB0036457 (Emodinanthranol)

Structure for HMDB0036457 (Emodinanthranol)

3D Structure for HMDB0036457 (Emodinanthranol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra