MiMeDB: Showing metabocard for emodin anthrone (MMDBc0054473)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:14:25 UTC

Update Date

2025-01-16 04:06:39 UTC

Metabolite ID

MMDBc0054473

Metabolite Identification

Common Name

emodin anthrone

Description

Emodinanthranol is found in alcoholic beverages. Emodinanthranol is isolated from Hypericum perforatum (St. John's wort).

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>
MMDBc0054473

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₅H₁₂O₄

Average Mass

256.2534

Monoisotopic Mass

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

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-06vi-0490000000-3844c5587cf9ac8d9d77	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0a4i-3416900000-59eff0fd88e587be6b12	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-34be4117595323691e56	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0290000000-65bf1bc9c8af7509bcb0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ap0-4970000000-e316817877a6dcba7058	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-0e95958fee1b3636638f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0090000000-b4c5436689f642a04dae	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0btc-4490000000-2dfcad46e64d13e876d7	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-b46e3a63d530434294a2	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-c413cebb2f7c69ce4ba4	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00bi-1790000000-eb54bd90c1ad1df4714d	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-82e226df9342cd67d796	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0090000000-82e226df9342cd67d796	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0c00-0390000000-dc620c507710a2e8fc8f	2021-09-24	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (void)	2025-10-24	67.2
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-24	25.2
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	404.3
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	591.7
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	631.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	308.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	1960.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-24	68.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	330.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	308.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	112.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	177.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	141.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-24	74.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	338.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	231.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	378.3
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1420.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	997.4

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	emodin anthrone_TMS_1	CC1=CC2=C(C(=O)C3=C(O)C=C(O)C=C3C2)C(O[Si](C)(C)C)=C1	standard non polar	2025-10-24	2079.32
Gas Chromatography	emodin anthrone_TMS_2	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3CC2=C1	standard non polar	2025-10-24	1473.54
Gas Chromatography	emodin anthrone_TMS_3	CC1=CC(O)=C2C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3CC2=C1	standard non polar	2025-10-24	2209.76
Gas Chromatography	emodin anthrone_TMS_4	CC1=CC2=C(C(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C)C2)C(O[Si](C)(C)C)=C1	standard non polar	2025-10-24	2185.77
Gas Chromatography	emodin anthrone_TMS_5	CC1=CC2=C(C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3C2)C(O[Si](C)(C)C)=C1	standard non polar	2025-10-24	1731.35
Gas Chromatography	emodin anthrone_TMS_6	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3CC2=C1	standard non polar	2025-10-24	2191.88
Gas Chromatography	emodin anthrone_TMS_7	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	standard non polar	2025-10-24	2046.6
Gas Chromatography	emodin anthrone_TMS_1	CC1=CC2=C(C(=O)C3=C(O)C=C(O)C=C3C2)C(O[Si](C)(C)C)=C1	standard polar	2025-10-24	2505.7
Gas Chromatography	emodin anthrone_TMS_2	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3CC2=C1	standard polar	2025-10-24	2442.37
Gas Chromatography	emodin anthrone_TMS_3	CC1=CC(O)=C2C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3CC2=C1	standard polar	2025-10-24	1599.69
Gas Chromatography	emodin anthrone_TMS_4	CC1=CC2=C(C(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C)C2)C(O[Si](C)(C)C)=C1	standard polar	2025-10-24	2224.0
Gas Chromatography	emodin anthrone_TMS_5	CC1=CC2=C(C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3C2)C(O[Si](C)(C)C)=C1	standard polar	2025-10-24	1789.01
Gas Chromatography	emodin anthrone_TMS_6	CC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3CC2=C1	standard polar	2025-10-24	2589.0
Gas Chromatography	emodin anthrone_TMS_7	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	standard polar	2025-10-24	2045.61

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	10	Human feces

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0036457

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

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for emodin anthrone (MMDBc0054473)

MOL for #<Metabolite:0x00007f9ac47ecbe0>

3D MOL for #<Metabolite:0x00007f9ac47ecbe0>

3D SDF for #<Metabolite:0x00007f9ac47ecbe0>

3D-SDF for #<Metabolite:0x00007f9ac47ecbe0>

PDB for #<Metabolite:0x00007f9ac47ecbe0>

3D PDB for #<Metabolite:0x00007f9ac47ecbe0>

SMILES for #<Metabolite:0x00007f9ac47ecbe0>

INCHI for #<Metabolite:0x00007f9ac47ecbe0>

Structure for #<Metabolite:0x00007f9ac47ecbe0>

3D Structure for #<Metabolite:0x00007f9ac47ecbe0>