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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:33:10 UTC

Update Date

2022-03-07 02:53:51 UTC

HMDB ID

HMDB0033790

Secondary Accession Numbers

HMDB33790

Metabolite Identification

Common Name

1,2,8-Trihydroxy-3-methylanthraquinone

Description

1,2,8-Trihydroxy-3-methylanthraquinone, also known as norobtusifolin or 2-hydroxychrysophanol, 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, 1,2,8-trihydroxy-3-methylanthraquinone is considered to be an aromatic polyketide. Based on a literature review very few articles have been published on 1,2,8-Trihydroxy-3-methylanthraquinone.

Structure

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

HMDB0033790
     RDKit          3D
1,2,8-Trihydroxy-3-methylanthraquinone
 30 32  0  0  0  0  0  0  0  0999 V2000
   -4.2107   -1.4572   -0.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9276   -0.7918   -0.4928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7048   -1.3688   -0.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130   -0.7628   -0.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5041    0.4641    0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7395    1.0566    0.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7334    2.2894    1.0892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9254    0.4560    0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1781    0.9933    0.3609 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7506    1.1170    0.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7032    2.2364    1.1415 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0472    0.5157    0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2512    1.1214    0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2975    2.3361    1.2754 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4632    0.4889    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4723   -0.7352   -0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2679   -1.3194   -0.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0532   -0.7272   -0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7842   -1.3707   -0.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8067   -2.5010   -1.2280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0213   -1.0846   -0.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5157   -1.1837   -1.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1686   -2.5575   -0.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6765   -2.3480   -1.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5723    2.7860    1.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2546    1.8868    0.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765    2.9973    1.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3672    0.9776    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4285   -1.2364   -0.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2761   -2.2784   -1.0366 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  5 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  2  0
 18 19  1  0
 19 20  2  0
  8  2  1  0
 18 12  1  0
 19  4  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  7 25  1  0
  9 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END


  Mrv0541 05061307212D          

 20 22  0  0  0  0            999 V2000
    0.0000    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
    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    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
    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
    0.7145    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
    1.4289    2.4750    0.0000 C   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
    0.0000    2.4750    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
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  1  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  4  2  0  0  0  0
 10  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11  8  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16  9  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  2  0  0  0  0
 19 14  2  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033790

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC2=C(C(O)=C1O)C(=O)C1=C(C=CC=C1O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O5/c1-6-5-8-11(15(20)12(6)17)14(19)10-7(13(8)18)3-2-4-9(10)16/h2-5,16-17,20H,1H3

> <INCHI_KEY>
CQNVSNFEXPKHGW-UHFFFAOYSA-N

> <FORMULA>
C15H10O5

> <MOLECULAR_WEIGHT>
270.2369

> <EXACT_MASS>
270.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.431500706347425

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2,8-trihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
3.821431499

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.418449822264439

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.930018051689951

> <JCHEM_PKA_STRONGEST_BASIC>
-4.446928852572625

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
72.1349

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxychrysophanol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033790
     RDKit          3D
1,2,8-Trihydroxy-3-methylanthraquinone
 30 32  0  0  0  0  0  0  0  0999 V2000
   -4.2107   -1.4572   -0.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9276   -0.7918   -0.4928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7048   -1.3688   -0.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130   -0.7628   -0.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5041    0.4641    0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7395    1.0566    0.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7334    2.2894    1.0892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9254    0.4560    0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1781    0.9933    0.3609 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7506    1.1170    0.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7032    2.2364    1.1415 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0472    0.5157    0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2512    1.1214    0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2975    2.3361    1.2754 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4632    0.4889    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4723   -0.7352   -0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2679   -1.3194   -0.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0532   -0.7272   -0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7842   -1.3707   -0.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8067   -2.5010   -1.2280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0213   -1.0846   -0.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5157   -1.1837   -1.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1686   -2.5575   -0.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6765   -2.3480   -1.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5723    2.7860    1.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2546    1.8868    0.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765    2.9973    1.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3672    0.9776    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4285   -1.2364   -0.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2761   -2.2784   -1.0366 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  5 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  2  0
 18 19  1  0
 19 20  2  0
  8  2  1  0
 18 12  1  0
 19  4  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  7 25  1  0
  9 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    3    4                                                       
CONECT    3    2    7                                                       
CONECT    4    2    9                                                       
CONECT    5    6    8                                                       
CONECT    6    1    5   12                                                  
CONECT    7    3   10   13                                                  
CONECT    8    5   11   13                                                  
CONECT    9    4   10   16                                                  
CONECT   10    7    9   14                                                  
CONECT   11    8   14   15                                                  
CONECT   12    6   15   17                                                  
CONECT   13    7    8   18                                                  
CONECT   14   10   11   19                                                  
CONECT   15   11   12   20                                                  
CONECT   16    9                                                            
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0033790
HETATM    1  C1  UNL     1      -4.211  -1.457  -0.868  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.928  -0.792  -0.493  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.705  -1.369  -0.742  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.513  -0.763  -0.400  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.504   0.464   0.215  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.740   1.057   0.472  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.733   2.289   1.089  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.925   0.456   0.132  1.00  0.00           C  
HETATM    9  O2  UNL     1      -4.178   0.993   0.361  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.751   1.117   0.582  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.703   2.236   1.142  1.00  0.00           O  
HETATM   12  C9  UNL     1       2.047   0.516   0.323  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.251   1.121   0.665  1.00  0.00           C  
HETATM   14  O4  UNL     1       3.298   2.336   1.275  1.00  0.00           O  
HETATM   15  C11 UNL     1       4.463   0.489   0.388  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.472  -0.735  -0.225  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.268  -1.319  -0.557  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.053  -0.727  -0.299  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.784  -1.371  -0.663  1.00  0.00           C  
HETATM   20  O5  UNL     1       0.807  -2.501  -1.228  1.00  0.00           O  
HETATM   21  H1  UNL     1      -5.021  -1.085  -0.207  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.516  -1.184  -1.902  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.169  -2.557  -0.713  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.677  -2.348  -1.232  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.572   2.786   1.311  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.255   1.887   0.806  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.677   2.997   1.587  1.00  0.00           H  
HETATM   28  H8  UNL     1       5.367   0.978   0.662  1.00  0.00           H  
HETATM   29  H9  UNL     1       5.429  -1.236  -0.445  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.276  -2.278  -1.037  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3    8
CONECT    3    4   24
CONECT    4    5    5   19
CONECT    5    6   10
CONECT    6    7    8    8
CONECT    7   25
CONECT    8    9
CONECT    9   26
CONECT   10   11   11   12
CONECT   12   13   13   18
CONECT   13   14   15
CONECT   14   27
CONECT   15   16   16   28
CONECT   16   17   29
CONECT   17   18   18   30
CONECT   18   19
CONECT   19   20   20
END

HMDB0033790
     RDKit          3D
1,2,8-Trihydroxy-3-methylanthraquinone
 30 32  0  0  0  0  0  0  0  0999 V2000
   -4.2107   -1.4572   -0.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9276   -0.7918   -0.4928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7048   -1.3688   -0.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130   -0.7628   -0.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5041    0.4641    0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7395    1.0566    0.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7334    2.2894    1.0892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9254    0.4560    0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1781    0.9933    0.3609 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7506    1.1170    0.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7032    2.2364    1.1415 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0472    0.5157    0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2512    1.1214    0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2975    2.3361    1.2754 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4632    0.4889    0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4723   -0.7352   -0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2679   -1.3194   -0.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0532   -0.7272   -0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7842   -1.3707   -0.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8067   -2.5010   -1.2280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0213   -1.0846   -0.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5157   -1.1837   -1.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1686   -2.5575   -0.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6765   -2.3480   -1.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5723    2.7860    1.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2546    1.8868    0.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765    2.9973    1.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3672    0.9776    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4285   -1.2364   -0.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2761   -2.2784   -1.0366 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  5 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  2  0
 18 19  1  0
 19 20  2  0
  8  2  1  0
 18 12  1  0
 19  4  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  7 25  1  0
  9 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Norobtusifolin	ChEBI
2-Hydroxychrysophanol	Kegg
1,2,8-Trihydroxy-3-methyl-9,10-anthracenedione, 9ci	HMDB

Chemical Formula

C₁₅H₁₀O₅

Average Molecular Weight

270.2369

Monoisotopic Molecular Weight

270.05282343

IUPAC Name

1,2,8-trihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

2-hydroxychrysophanol

CAS Registry Number

Not Available

SMILES

CC1=CC2=C(C(O)=C1O)C(=O)C1=C(C=CC=C1O)C2=O

InChI Identifier

InChI=1S/C15H10O5/c1-6-5-8-11(15(20)12(6)17)14(19)10-7(13(8)18)3-2-4-9(10)16/h2-5,16-17,20H,1H3

InChI Key

CQNVSNFEXPKHGW-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
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

hydroxyanthraquinones (CHEBI:7635 )
Anthracenes and phenanthrenes (C10379 )
Anthraquinone type (C10379 )
Anthracenes and phenanthrenes (LMPK13040011 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033790)

Cellular substructure

Membrane (HMDB: HMDB0033790)

Source

Exogenous

Food

Food (HMDB: HMDB0033790)

Not Available

Nutrient (HMDB: HMDB0033790)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	265 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.24 g/L	ALOGPS
logP	2.71	ALOGPS
logP	3.82	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.93	ChemAxon
pKa (Strongest Basic)	-4.4	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	0	ChemAxon
Refractivity	72.13 m³·mol⁻¹	ChemAxon
Polarizability	26.43 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]+	160.185	31661259
DarkChem	[M-H]-	160.02	31661259
DeepCCS	[M+H]+	159.293	30932474
DeepCCS	[M-H]-	156.935	30932474
DeepCCS	[M-2H]-	189.938	30932474
DeepCCS	[M+Na]+	165.386	30932474
AllCCS	[M+H]+	159.6	32859911
AllCCS	[M+H-H2O]+	155.8	32859911
AllCCS	[M+NH4]+	163.2	32859911
AllCCS	[M+Na]+	164.2	32859911
AllCCS	[M-H]-	161.1	32859911
AllCCS	[M+Na-2H]-	160.3	32859911
AllCCS	[M+HCOO]-	159.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2,8-Trihydroxy-3-methylanthraquinone	CC1=CC2=C(C(O)=C1O)C(=O)C1=C(C=CC=C1O)C2=O	3772.8	Standard polar	33892256
1,2,8-Trihydroxy-3-methylanthraquinone	CC1=CC2=C(C(O)=C1O)C(=O)C1=C(C=CC=C1O)C2=O	2353.4	Standard non polar	33892256
1,2,8-Trihydroxy-3-methylanthraquinone	CC1=CC2=C(C(O)=C1O)C(=O)C1=C(C=CC=C1O)C2=O	2556.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,2,8-Trihydroxy-3-methylanthraquinone,1TMS,isomer #1	CC1=CC2=C(C(=O)C3=C(O)C=CC=C3C2=O)C(O[Si](C)(C)C)=C1O	2677.4	Semi standard non polar	33892256
1,2,8-Trihydroxy-3-methylanthraquinone,1TMS,isomer #2	CC1=CC2=C(C(=O)C3=C(O)C=CC=C3C2=O)C(O)=C1O[Si](C)(C)C	2684.9	Semi standard non polar	33892256
1,2,8-Trihydroxy-3-methylanthraquinone,1TMS,isomer #3	CC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C2=O)C(O)=C1O	2693.4	Semi standard non polar	33892256
1,2,8-Trihydroxy-3-methylanthraquinone,2TMS,isomer #1	CC1=CC2=C(C(=O)C3=C(O)C=CC=C3C2=O)C(O[Si](C)(C)C)=C1O[Si](C)(C)C	2610.7	Semi standard non polar	33892256
1,2,8-Trihydroxy-3-methylanthraquinone,2TMS,isomer #2	CC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C2=O)C(O[Si](C)(C)C)=C1O	2716.7	Semi standard non polar	33892256
1,2,8-Trihydroxy-3-methylanthraquinone,2TMS,isomer #3	CC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C2=O)C(O)=C1O[Si](C)(C)C	2739.2	Semi standard non polar	33892256
1,2,8-Trihydroxy-3-methylanthraquinone,3TMS,isomer #1	CC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C2=O)C(O[Si](C)(C)C)=C1O[Si](C)(C)C	2694.0	Semi standard non polar	33892256
1,2,8-Trihydroxy-3-methylanthraquinone,1TBDMS,isomer #1	CC1=CC2=C(C(=O)C3=C(O)C=CC=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C1O	2938.9	Semi standard non polar	33892256
1,2,8-Trihydroxy-3-methylanthraquinone,1TBDMS,isomer #2	CC1=CC2=C(C(=O)C3=C(O)C=CC=C3C2=O)C(O)=C1O[Si](C)(C)C(C)(C)C	2949.0	Semi standard non polar	33892256
1,2,8-Trihydroxy-3-methylanthraquinone,1TBDMS,isomer #3	CC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC=C3C2=O)C(O)=C1O	2954.3	Semi standard non polar	33892256
1,2,8-Trihydroxy-3-methylanthraquinone,2TBDMS,isomer #1	CC1=CC2=C(C(=O)C3=C(O)C=CC=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3123.3	Semi standard non polar	33892256
1,2,8-Trihydroxy-3-methylanthraquinone,2TBDMS,isomer #2	CC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C1O	3228.0	Semi standard non polar	33892256
1,2,8-Trihydroxy-3-methylanthraquinone,2TBDMS,isomer #3	CC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC=C3C2=O)C(O)=C1O[Si](C)(C)C(C)(C)C	3252.8	Semi standard non polar	33892256
1,2,8-Trihydroxy-3-methylanthraquinone,3TBDMS,isomer #1	CC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3388.4	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 - 1,2,8-Trihydroxy-3-methylanthraquinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6y-0690000000-3b4056add4f82209afa3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone GC-MS (3 TMS) - 70eV, Positive	splash10-0229-3231900000-3581e0990d21e90aa1f2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 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 - 1,2,8-Trihydroxy-3-methylanthraquinone 10V, Positive-QTOF	splash10-00di-0090000000-6c8512ee17fc07f0572c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 20V, Positive-QTOF	splash10-00di-0690000000-6934ae2059d0ab40cfc9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 40V, Positive-QTOF	splash10-0v4j-6960000000-502dd39ea62e1d644a85	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 10V, Negative-QTOF	splash10-014i-0090000000-c93b46e1ac5c7e15bd03	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 20V, Negative-QTOF	splash10-014i-0090000000-1d36ebd33544f740b13f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 40V, Negative-QTOF	splash10-0gi1-3960000000-ba844b84ee063f3cb7a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 10V, Negative-QTOF	splash10-014i-0090000000-4e65ba44fc45f7e80f5a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 20V, Negative-QTOF	splash10-014i-0090000000-42a19a2704a40c833978	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 40V, Negative-QTOF	splash10-03di-0090000000-6c8884d874b5ccbb2de1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 10V, Positive-QTOF	splash10-00di-0090000000-ae6e5e86465295cd0332	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 20V, Positive-QTOF	splash10-00di-0090000000-ae6e5e86465295cd0332	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,8-Trihydroxy-3-methylanthraquinone 40V, Positive-QTOF	splash10-0udi-3970000000-b396f31bda0eff3983b9	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

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

Not Available

METLIN ID

Not Available

PubChem Compound

442759

PDB ID

Not Available

ChEBI ID

7635

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 1,2,8-Trihydroxy-3-methylanthraquinone (HMDB0033790)

MOL for HMDB0033790 (1,2,8-Trihydroxy-3-methylanthraquinone)

3D MOL for HMDB0033790 (1,2,8-Trihydroxy-3-methylanthraquinone)

3D SDF for HMDB0033790 (1,2,8-Trihydroxy-3-methylanthraquinone)

3D-SDF for HMDB0033790 (1,2,8-Trihydroxy-3-methylanthraquinone)

PDB for HMDB0033790 (1,2,8-Trihydroxy-3-methylanthraquinone)

3D PDB for HMDB0033790 (1,2,8-Trihydroxy-3-methylanthraquinone)

SMILES for HMDB0033790 (1,2,8-Trihydroxy-3-methylanthraquinone)

INCHI for HMDB0033790 (1,2,8-Trihydroxy-3-methylanthraquinone)

Structure for HMDB0033790 (1,2,8-Trihydroxy-3-methylanthraquinone)

3D Structure for HMDB0033790 (1,2,8-Trihydroxy-3-methylanthraquinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra