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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:17 UTC

Update Date

2022-03-07 02:52:43 UTC

HMDB ID

HMDB0030829

Secondary Accession Numbers

HMDB30829

Metabolite Identification

Common Name

Aloeemodin

Description

Aloeemodin, also known as rhabarberone or rottlerin?, belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Thus, aloeemodin is considered to be an aromatic polyketide. Aloeemodin 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 significant number of articles have been published on Aloeemodin.

Structure

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

HMDB0030829
     RDKit          3D
Aloeemodin
 30 32  0  0  0  0  0  0  0  0999 V2000
   -0.2174    2.6970    0.8487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4283    1.5153    0.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7998    1.0380    0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8419    1.8760    0.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1540    1.4927    0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4410    0.2283    0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4137   -0.6765   -0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7358   -1.9225   -0.6800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0901   -0.2372   -0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9643   -1.1121   -0.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2524   -2.2642   -0.8654 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4267   -0.6748   -0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628   -1.5234   -0.6770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3055   -2.8061   -1.1231 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7663   -1.0319   -0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0013    0.2348   -0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3797    0.7395    0.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3235   -0.2159   -0.3195 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592    1.0558    0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549    0.6073    0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6590    2.8960    0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9809    2.1664    0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4501   -0.1533   -0.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3104   -2.7261   -0.9733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5054   -3.3089   -1.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5886   -1.6777   -0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5217    1.1375    1.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4886    1.5904   -0.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2119   -1.0020    0.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428    2.0576    0.5620 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  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20  2  1  0
  9  3  1  0
 20 12  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
 14 25  1  0
 15 26  1  0
 17 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
M  END


  Mrv0541 05061305322D          

 20 22  0  0  0  0            999 V2000
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    0.0000    0.0000    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
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  7  4  2  0  0  0  0
  7  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  2  1  0  0  0  0
  9  4  1  0  0  0  0
 10  3  2  0  0  0  0
 11  5  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  6  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 14  2  0  0  0  0
 20 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030829

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
YDQWDHRMZQUTBA-UHFFFAOYSA-N

> <FORMULA>
C15H10O5

> <MOLECULAR_WEIGHT>
270.2369

> <EXACT_MASS>
270.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.50761806525199

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
2.844225664

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.663975685695638

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.000869342448025

> <JCHEM_PKA_STRONGEST_BASIC>
-2.945233505196912

> <JCHEM_POLAR_SURFACE_AREA>
94.82999999999998

> <JCHEM_REFRACTIVITY>
71.9287

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aloe emodin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030829
     RDKit          3D
Aloeemodin
 30 32  0  0  0  0  0  0  0  0999 V2000
   -0.2174    2.6970    0.8487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4283    1.5153    0.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7998    1.0380    0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8419    1.8760    0.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1540    1.4927    0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4410    0.2283    0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4137   -0.6765   -0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7358   -1.9225   -0.6800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0901   -0.2372   -0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9643   -1.1121   -0.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2524   -2.2642   -0.8654 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4267   -0.6748   -0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628   -1.5234   -0.6770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3055   -2.8061   -1.1231 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7663   -1.0319   -0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0013    0.2348   -0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3797    0.7395    0.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3235   -0.2159   -0.3195 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592    1.0558    0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549    0.6073    0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6590    2.8960    0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9809    2.1664    0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4501   -0.1533   -0.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3104   -2.7261   -0.9733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5054   -3.3089   -1.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5886   -1.6777   -0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5217    1.1375    1.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4886    1.5904   -0.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2119   -1.0020    0.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428    2.0576    0.5620 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  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20  2  1  0
  9  3  1  0
 20 12  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
 14 25  1  0
 15 26  1  0
 17 27  1  0
 17 28  1  0
 18 29  1  0
 19 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       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   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       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       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    8                                                       
CONECT    3    1   10                                                       
CONECT    4    7    9                                                       
CONECT    5    7   11                                                       
CONECT    6    7   16                                                       
CONECT    7    4    5    6                                                  
CONECT    8    2   12   14                                                  
CONECT    9    4   13   14                                                  
CONECT   10    3   12   17                                                  
CONECT   11    5   13   18                                                  
CONECT   12    8   10   15                                                  
CONECT   13    9   11   15                                                  
CONECT   14    8    9   19                                                  
CONECT   15   12   13   20                                                  
CONECT   16    6                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0030829
HETATM    1  O1  UNL     1      -0.217   2.697   0.849  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.428   1.515   0.439  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.800   1.038   0.308  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.842   1.876   0.630  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.154   1.493   0.530  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.441   0.228   0.094  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.414  -0.676  -0.251  1.00  0.00           C  
HETATM    8  O2  UNL     1      -3.736  -1.922  -0.680  1.00  0.00           O  
HETATM    9  C7  UNL     1      -2.090  -0.237  -0.132  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.964  -1.112  -0.469  1.00  0.00           C  
HETATM   11  O3  UNL     1      -1.252  -2.264  -0.865  1.00  0.00           O  
HETATM   12  C9  UNL     1       0.427  -0.675  -0.352  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.463  -1.523  -0.677  1.00  0.00           C  
HETATM   14  O4  UNL     1       1.305  -2.806  -1.123  1.00  0.00           O  
HETATM   15  C11 UNL     1       2.766  -1.032  -0.539  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.001   0.235  -0.100  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.380   0.740   0.040  1.00  0.00           C  
HETATM   18  O5  UNL     1       5.324  -0.216  -0.320  1.00  0.00           O  
HETATM   19  C14 UNL     1       1.959   1.056   0.215  1.00  0.00           C  
HETATM   20  C15 UNL     1       0.655   0.607   0.092  1.00  0.00           C  
HETATM   21  H1  UNL     1      -2.659   2.896   0.983  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.981   2.166   0.788  1.00  0.00           H  
HETATM   23  H3  UNL     1      -5.450  -0.153  -0.014  1.00  0.00           H  
HETATM   24  H4  UNL     1      -3.310  -2.726  -0.973  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.505  -3.309  -1.278  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.589  -1.678  -0.787  1.00  0.00           H  
HETATM   27  H7  UNL     1       4.522   1.137   1.058  1.00  0.00           H  
HETATM   28  H8  UNL     1       4.489   1.590  -0.693  1.00  0.00           H  
HETATM   29  H9  UNL     1       5.212  -1.002   0.290  1.00  0.00           H  
HETATM   30  H10 UNL     1       2.143   2.058   0.562  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4    4    9
CONECT    4    5   21
CONECT    5    6    6   22
CONECT    6    7   23
CONECT    7    8    9    9
CONECT    8   24
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   13   20
CONECT   13   14   15
CONECT   14   25
CONECT   15   16   16   26
CONECT   16   17   19
CONECT   17   18   27   28
CONECT   18   29
CONECT   19   20   20   30
END

HMDB0030829
     RDKit          3D
Aloeemodin
 30 32  0  0  0  0  0  0  0  0999 V2000
   -0.2174    2.6970    0.8487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4283    1.5153    0.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7998    1.0380    0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8419    1.8760    0.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1540    1.4927    0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4410    0.2283    0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4137   -0.6765   -0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7358   -1.9225   -0.6800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0901   -0.2372   -0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9643   -1.1121   -0.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2524   -2.2642   -0.8654 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4267   -0.6748   -0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628   -1.5234   -0.6770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3055   -2.8061   -1.1231 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7663   -1.0319   -0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0013    0.2348   -0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3797    0.7395    0.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3235   -0.2159   -0.3195 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592    1.0558    0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549    0.6073    0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6590    2.8960    0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9809    2.1664    0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4501   -0.1533   -0.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3104   -2.7261   -0.9733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5054   -3.3089   -1.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5886   -1.6777   -0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5217    1.1375    1.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4886    1.5904   -0.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2119   -1.0020    0.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428    2.0576    0.5620 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  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20  2  1  0
  9  3  1  0
 20 12  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
 14 25  1  0
 15 26  1  0
 17 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,8-Dihydroxy-3-hydroxymethylanthraquinone	ChEBI
3-(Hydroxymethyl)chrysazin	ChEBI
Aloe-emodin	ChEBI
Rhabarberone	ChEBI
1,8-Dihydroxy-3-(hydroxymethyl)-9,10-anthracenedione	HMDB
1,8-Dihydroxy-3-(hydroxymethyl)anthra-9,10-quinone	HMDB
1,8-Dihydroxy-3-(hydroxymethyl)anthraquinone	HMDB
1,8-Dihydroxy-3-hydroxymethyl-9,10-anthracenedione, 9ci	HMDB
1,8-Dihydroxy-3-hydroxymethyl-anthraquinone	HMDB
3-Hydroxymethylchrysazine	HMDB
Rottlerin?	HMDB
Aloe emodin	HMDB
Aloeemodin	ChEBI

Chemical Formula

C₁₅H₁₀O₅

Average Molecular Weight

270.2369

Monoisotopic Molecular Weight

270.05282343

IUPAC Name

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

Traditional Name

aloe emodin

CAS Registry Number

481-72-1

SMILES

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

InChI Identifier

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

InChI Key

YDQWDHRMZQUTBA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Anthraquinone
9,10-anthraquinone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

aromatic primary alcohol (CHEBI:2607 )
dihydroxyanthraquinone (CHEBI:2607 )
Anthracenes and phenanthrenes (C10294 )
Anthraquinone type (C10294 )
Anthracenes and phenanthrenes (LMPK13040002 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030829)
Cytoplasm (HMDB: HMDB0030829)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030829)

Source

Endogenous

Endogenous (HMDB: HMDB0030829)

Plant

Plant (HMDB: HMDB0030829)

Exogenous

Food

Food (HMDB: HMDB0030829)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	221 - 223 °C	Not Available
Boiling Point	568.82 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	45.8 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.254 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	2.39	ALOGPS
logP	2.84	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.93 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]+	162.728	31661259
DarkChem	[M-H]-	161.822	31661259
DeepCCS	[M+H]+	161.223	30932474
DeepCCS	[M-H]-	158.865	30932474
DeepCCS	[M-2H]-	191.857	30932474
DeepCCS	[M+Na]+	167.316	30932474
AllCCS	[M+H]+	160.3	32859911
AllCCS	[M+H-H2O]+	156.5	32859911
AllCCS	[M+NH4]+	163.8	32859911
AllCCS	[M+Na]+	164.8	32859911
AllCCS	[M-H]-	161.7	32859911
AllCCS	[M+Na-2H]-	161.0	32859911
AllCCS	[M+HCOO]-	160.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aloeemodin	OCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O	3804.4	Standard polar	33892256
Aloeemodin	OCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O	2503.2	Standard non polar	33892256
Aloeemodin	OCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O	2720.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Aloeemodin,1TMS,isomer #1	C[Si](C)(C)OCC1=CC(O)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C1	2681.5	Semi standard non polar	33892256
Aloeemodin,1TMS,isomer #2	C[Si](C)(C)OC1=CC(CO)=CC2=C1C(=O)C1=C(O)C=CC=C1C2=O	2647.3	Semi standard non polar	33892256
Aloeemodin,1TMS,isomer #3	C[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O)C=C(CO)C=C1C2=O	2666.6	Semi standard non polar	33892256
Aloeemodin,2TMS,isomer #1	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C1	2683.7	Semi standard non polar	33892256
Aloeemodin,2TMS,isomer #2	C[Si](C)(C)OCC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C(=O)C2=C1	2707.7	Semi standard non polar	33892256
Aloeemodin,2TMS,isomer #3	C[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C(CO)C=C1C2=O	2664.2	Semi standard non polar	33892256
Aloeemodin,3TMS,isomer #1	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C(=O)C2=C1	2735.7	Semi standard non polar	33892256
Aloeemodin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC(O)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C1	2943.2	Semi standard non polar	33892256
Aloeemodin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(CO)=CC2=C1C(=O)C1=C(O)C=CC=C1C2=O	2905.1	Semi standard non polar	33892256
Aloeemodin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O)C=C(CO)C=C1C2=O	2923.3	Semi standard non polar	33892256
Aloeemodin,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=CC=C3C(=O)C2=C1	3132.2	Semi standard non polar	33892256
Aloeemodin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1=CC(O)=C2C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC=C3C(=O)C2=C1	3181.9	Semi standard non polar	33892256
Aloeemodin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(CO)C=C1C2=O	3167.9	Semi standard non polar	33892256
Aloeemodin,3TBDMS,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=CC=C3C(=O)C2=C1	3385.7	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 - Aloeemodin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-0490000000-0bd7d78de4ab72cee499	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aloeemodin GC-MS (3 TMS) - 70eV, Positive	splash10-00di-9335800000-8354afcd5801dd9e226a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aloeemodin 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aloeemodin 45V, Positive-QTOF	splash10-00di-0090000000-89a9cdbc914be4f31ef0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aloeemodin 30V, Negative-QTOF	splash10-014i-0900000000-1f7f05d70e145262a8ae	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aloeemodin 50V, Negative-QTOF	splash10-014i-0900000000-2ae7958aaa4974262436	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aloeemodin 60V, Positive-QTOF	splash10-00di-1890000000-1bcbfa331cd0f56b0519	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aloeemodin 90V, Positive-QTOF	splash10-014i-9700000000-1b6342ee504925cf8712	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aloeemodin 75V, Positive-QTOF	splash10-0gi0-4910000000-2e7abe7e97dced7a4fd6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aloeemodin 15V, Positive-QTOF	splash10-00di-0090000000-2f4d012dbc11d78cb7fd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aloeemodin 30V, Positive-QTOF	splash10-00di-0090000000-ae6e5e86465295cd0332	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aloeemodin 6V, Positive-QTOF	splash10-014i-0090000000-33131ad58113b1ea5a1a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aloeemodin 50V, Positive-QTOF	splash10-0f6x-5900000000-421c17b03cf15fb79629	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aloeemodin 30V, Positive-QTOF	splash10-0fk9-1970000000-869440dbcfb69ad60b6c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aloeemodin 10V, Positive-QTOF	splash10-00di-0190000000-93b116cb88147c1246f8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aloeemodin 10V, Positive-QTOF	splash10-00di-0090000000-a08aa7ee329d4ff27f60	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aloeemodin 50V, Positive-QTOF	splash10-0gbc-5900000000-e0ea1aecea08fb1b67bb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aloeemodin 6V, Positive-QTOF	splash10-014i-0900000000-8453dca9bdc4d7faec67	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aloeemodin 30V, Positive-QTOF	splash10-0fk9-0970000000-ef8922c4a65810a2f2c9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aloeemodin 30V, Positive-QTOF	splash10-0fk9-0960000000-e84a183db3b91f5702da	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aloeemodin 6V, Positive-QTOF	splash10-0udi-0090000000-d2f0783b46bac268d0df	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aloeemodin 50V, Positive-QTOF	splash10-0gbc-4900000000-f81771cbd943d0418544	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aloeemodin 10V, Positive-QTOF	splash10-00di-0090000000-0e840b8245048a00c03d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aloeemodin 20V, Positive-QTOF	splash10-0fk9-0690000000-b4decba7d1a879148840	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aloeemodin 40V, Positive-QTOF	splash10-0uk9-6980000000-d1cc4a7d015592f25821	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aloeemodin 10V, Negative-QTOF	splash10-014i-0090000000-c444047e5e27050701b9	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aloeemodin 20V, Negative-QTOF	splash10-014r-0090000000-1c009306edea3d4227b8	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aloeemodin 40V, Negative-QTOF	splash10-000l-5590000000-ac4566b9723c0c91620c	2016-08-04	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

Aloe_emodin

METLIN ID

Not Available

PubChem Compound

10207

PDB ID

Not Available

ChEBI ID

2607

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1665291

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Paszkiewicz-Gadek A, Chlabicz J, Galasinski W: The influence of selected potential oncostatics of plant origin on the protein biosynthesis in vitro. Pol J Pharmacol Pharm. 1988 Mar-Apr;40(2):183-90. [PubMed:3237568 ]
Heidemann A, Volkner W, Mengs U: Genotoxicity of aloeemodin in vitro and in vivo. Mutat Res. 1996 Mar 1;367(3):123-33. [PubMed:8600368 ]
Galasinski W, Chlabicz J, Paszkiewicz-Gadek A, Marcinkiewicz C, Gindzienski A: The substances of plant origin that inhibit protein biosynthesis. Acta Pol Pharm. 1996 Sep-Oct;53(5):311-8. [PubMed:9415207 ]
Xu F, Liu Y, Dong H, Song R, Zhang Z: Pharmacokinetic comparison in rats of six bioactive compounds between Da-Cheng-Qi decoction and its parent herbal medicines. Nat Prod Commun. 2010 May;5(5):795-800. [PubMed:20521549 ]
Zan B, Shi R, Wang T, Wu J, Ma Y, Cheng N: Simultaneous quantification of multiple active components from Xiexin decoction in rat plasma by LC-ESI-MS/MS: application in pharmacokinetics. Biomed Chromatogr. 2011 Jul;25(7):816-26. doi: 10.1002/bmc.1521. Epub 2010 Sep 27. [PubMed:20872909 ]
Mengs U, Grimminger W, Krumbiegel G, Schuler D, Silber W, Volkner W: No clastogenic activity of a senna extract in the mouse micronucleus assay. Mutat Res. 1999 Aug 18;444(2):421-6. [PubMed:10521682 ]
Dong XJ, Zhu YF, Bao GH, Hu FL, Qin GW: New limonoids and a dihydrobenzofuran norlignan from the roots of Toona sinensis. Molecules. 2013 Mar 1;18(3):2840-50. doi: 10.3390/molecules18032840. [PubMed:23455673 ]
Saleem R, Faizi S, Siddiqui BS, Ahmed M, Hussain SA, Qazi A, Dar A, Ahmad SI, Qazi MH, Akhtar S, Hasnain SN: Hypotensive effect of chemical constituents from Aloe barbadensis. Planta Med. 2001 Nov;67(8):757-60. [PubMed:11731923 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Aloeemodin (HMDB0030829)

MOL for HMDB0030829 (Aloeemodin)

3D MOL for HMDB0030829 (Aloeemodin)

3D SDF for HMDB0030829 (Aloeemodin)

3D-SDF for HMDB0030829 (Aloeemodin)

PDB for HMDB0030829 (Aloeemodin)

3D PDB for HMDB0030829 (Aloeemodin)

SMILES for HMDB0030829 (Aloeemodin)

INCHI for HMDB0030829 (Aloeemodin)

Structure for HMDB0030829 (Aloeemodin)

3D Structure for HMDB0030829 (Aloeemodin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra