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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:20:44 UTC

Update Date

2022-03-07 02:55:11 UTC

HMDB ID

HMDB0037101

Secondary Accession Numbers

HMDB37101

Metabolite Identification

Common Name

8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid

Description

8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system. Based on a literature review a significant number of articles have been published on 8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid.

Structure

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

HMDB0037101
     RDKit          3D
8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid
 35 37  0  0  0  0  0  0  0  0999 V2000
    3.9364    2.4727   -0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416    1.0846   -0.1434 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4772    0.5420   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023    1.3634   -0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1404    0.7936   -0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0019   -0.5702    0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1149   -1.4351    0.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8470   -2.8681    0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3566   -0.8543    0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5613   -1.6284    0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6961   -2.8615    0.1677 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8107   -0.9476   -0.0087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3620   -1.1091    0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4851   -2.3487    0.2485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5387   -0.2318    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8058   -0.7601    0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0877   -2.0930    0.2896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9436    0.0942    0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7743    1.4436    0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4997    1.9626   -0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3880    1.1290   -0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0456    1.6703   -0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355    2.9030   -0.1789 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9801    2.6750   -0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2844    2.8378   -1.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6897    3.0279    0.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4931    2.4220   -0.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3003   -3.2947   -0.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3455   -3.1508    1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7801   -3.4438    0.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1878   -0.7776   -0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4901   -2.8396    0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9441   -0.3289    0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6421    2.0998   -0.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3014    3.0217   -0.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
  9  3  1  0
 21 15  1  0
 22  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 12 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END

  Mrv0541 05061309342D          

 23 25  0  0  0  0            999 V2000
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  1  1  0  0  0  0
  8  4  1  0  0  0  0
  9  6  2  0  0  0  0
 10  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14  8  2  0  0  0  0
 14 10  1  0  0  0  0
 15  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 13  1  0  0  0  0
 18 10  1  0  0  0  0
 19 15  2  0  0  0  0
 20 16  2  0  0  0  0
 21 17  2  0  0  0  0
 22 17  1  0  0  0  0
 23  2  1  0  0  0  0
 23 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037101

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(C(O)=O)C(C)=C2C(=O)C3=C(C=CC=C3O)C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O6/c1-7-12-9(6-11(23-2)13(7)17(21)22)15(19)8-4-3-5-10(18)14(8)16(12)20/h3-6,18H,1-2H3,(H,21,22)

> <INCHI_KEY>
QYKOMVRHNZHDBN-UHFFFAOYSA-N

> <FORMULA>
C17H12O6

> <MOLECULAR_WEIGHT>
312.2736

> <EXACT_MASS>
312.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
30.626658406032014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-3-methoxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

> <ALOGPS_LOGP>
2.08

> <JCHEM_LOGP>
3.2784737846666663

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.43117335992577

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1649035928715756

> <JCHEM_PKA_STRONGEST_BASIC>
-4.444769295102414

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
81.89249999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.09e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-3-methoxy-1-methyl-9,10-dioxoanthracene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037101
     RDKit          3D
8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid
 35 37  0  0  0  0  0  0  0  0999 V2000
    3.9364    2.4727   -0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416    1.0846   -0.1434 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4772    0.5420   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023    1.3634   -0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1404    0.7936   -0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0019   -0.5702    0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1149   -1.4351    0.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8470   -2.8681    0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3566   -0.8543    0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5613   -1.6284    0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6961   -2.8615    0.1677 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8107   -0.9476   -0.0087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3620   -1.1091    0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4851   -2.3487    0.2485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5387   -0.2318    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8058   -0.7601    0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0877   -2.0930    0.2896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9436    0.0942    0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7743    1.4436    0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4997    1.9626   -0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3880    1.1290   -0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0456    1.6703   -0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355    2.9030   -0.1789 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9801    2.6750   -0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2844    2.8378   -1.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6897    3.0279    0.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4931    2.4220   -0.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3003   -3.2947   -0.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3455   -3.1508    1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7801   -3.4438    0.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1878   -0.7776   -0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4901   -2.8396    0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9441   -0.3289    0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6421    2.0998   -0.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3014    3.0217   -0.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
  9  3  1  0
 21 15  1  0
 22  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 12 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  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       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2   23                                                            
CONECT    3    4    5                                                       
CONECT    4    3    8                                                       
CONECT    5    3   10                                                       
CONECT    6    9   11                                                       
CONECT    7    1   12   13                                                  
CONECT    8    4   14   15                                                  
CONECT    9    6   12   15                                                  
CONECT   10    5   14   18                                                  
CONECT   11    6   13   23                                                  
CONECT   12    7    9   16                                                  
CONECT   13    7   11   17                                                  
CONECT   14    8   10   16                                                  
CONECT   15    8    9   19                                                  
CONECT   16   12   14   20                                                  
CONECT   17   13   21   22                                                  
CONECT   18   10                                                            
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   17                                                            
CONECT   22   17                                                            
CONECT   23    2   11                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0037101
HETATM    1  C1  UNL     1       3.936   2.473  -0.257  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.742   1.085  -0.143  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.477   0.542  -0.071  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.402   1.363  -0.111  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.140   0.794  -0.036  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.002  -0.570   0.074  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.115  -1.435   0.116  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.847  -2.868   0.234  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.357  -0.854   0.041  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.561  -1.628   0.074  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.696  -2.862   0.168  1.00  0.00           O  
HETATM   12  O3  UNL     1       4.811  -0.948  -0.009  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.362  -1.109   0.148  1.00  0.00           C  
HETATM   14  O4  UNL     1      -1.485  -2.349   0.248  1.00  0.00           O  
HETATM   15  C11 UNL     1      -2.539  -0.232   0.107  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.806  -0.760   0.178  1.00  0.00           C  
HETATM   17  O5  UNL     1      -4.088  -2.093   0.290  1.00  0.00           O  
HETATM   18  C13 UNL     1      -4.944   0.094   0.138  1.00  0.00           C  
HETATM   19  C14 UNL     1      -4.774   1.444   0.028  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.500   1.963  -0.042  1.00  0.00           C  
HETATM   21  C16 UNL     1      -2.388   1.129  -0.003  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.046   1.670  -0.077  1.00  0.00           C  
HETATM   23  O6  UNL     1      -0.835   2.903  -0.179  1.00  0.00           O  
HETATM   24  H1  UNL     1       4.980   2.675  -0.588  1.00  0.00           H  
HETATM   25  H2  UNL     1       3.284   2.838  -1.079  1.00  0.00           H  
HETATM   26  H3  UNL     1       3.690   3.028   0.674  1.00  0.00           H  
HETATM   27  H4  UNL     1       1.493   2.422  -0.196  1.00  0.00           H  
HETATM   28  H5  UNL     1       0.300  -3.295  -0.658  1.00  0.00           H  
HETATM   29  H6  UNL     1       0.346  -3.151   1.205  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.780  -3.444   0.254  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.188  -0.778  -0.924  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.490  -2.840   0.334  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.944  -0.329   0.195  1.00  0.00           H  
HETATM   34  H11 UNL     1      -5.642   2.100  -0.003  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.301   3.022  -0.130  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   27
CONECT    5    6    6   22
CONECT    6    7   13
CONECT    7    8    9    9
CONECT    8   28   29   30
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   31
CONECT   13   14   14   15
CONECT   15   16   16   21
CONECT   16   17   18
CONECT   17   32
CONECT   18   19   19   33
CONECT   19   20   34
CONECT   20   21   21   35
CONECT   21   22
CONECT   22   23   23
END

HMDB0037101
     RDKit          3D
8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid
 35 37  0  0  0  0  0  0  0  0999 V2000
    3.9364    2.4727   -0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416    1.0846   -0.1434 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4772    0.5420   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023    1.3634   -0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1404    0.7936   -0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0019   -0.5702    0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1149   -1.4351    0.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8470   -2.8681    0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3566   -0.8543    0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5613   -1.6284    0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6961   -2.8615    0.1677 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8107   -0.9476   -0.0087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3620   -1.1091    0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4851   -2.3487    0.2485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5387   -0.2318    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8058   -0.7601    0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0877   -2.0930    0.2896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9436    0.0942    0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7743    1.4436    0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4997    1.9626   -0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3880    1.1290   -0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0456    1.6703   -0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355    2.9030   -0.1789 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9801    2.6750   -0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2844    2.8378   -1.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6897    3.0279    0.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4931    2.4220   -0.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3003   -3.2947   -0.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3455   -3.1508    1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7801   -3.4438    0.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1878   -0.7776   -0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4901   -2.8396    0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9441   -0.3289    0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6421    2.0998   -0.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3014    3.0217   -0.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
  9  3  1  0
 21 15  1  0
 22  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 12 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylate	Generator
8-Hydroxy-3-methoxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate	HMDB

Chemical Formula

C₁₇H₁₂O₆

Average Molecular Weight

312.2736

Monoisotopic Molecular Weight

312.063388116

IUPAC Name

8-hydroxy-3-methoxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Traditional Name

8-hydroxy-3-methoxy-1-methyl-9,10-dioxoanthracene-2-carboxylic acid

CAS Registry Number

176327-86-9

SMILES

COC1=C(C(O)=O)C(C)=C2C(=O)C3=C(C=CC=C3O)C(=O)C2=C1

InChI Identifier

InChI=1S/C17H12O6/c1-7-12-9(6-11(23-2)13(7)17(21)22)15(19)8-4-3-5-10(18)14(8)16(12)20/h3-6,18H,1-2H3,(H,21,22)

InChI Key

QYKOMVRHNZHDBN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Anthracenecarboxylic acids and derivatives

Direct Parent

Anthracenecarboxylic acids

Alternative Parents

Substituents

Anthracene carboxylic acid
9,10-anthraquinone
Anthraquinone
2-naphthalenecarboxylic acid or derivatives
2-naphthalenecarboxylic acid
O-methoxybenzoic acid or derivatives
Anisole
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Vinylogous acid
Ketone
Ether
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037101)
Cytoplasm (HMDB: HMDB0037101)

Source

Exogenous

Exogenous (HMDB: HMDB0037101)

Food

Food (HMDB: HMDB0037101)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037101)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	7.62 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	0.061 g/L	ALOGPS
logP	2.08	ALOGPS
logP	3.28	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	3.16	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.89 m³·mol⁻¹	ChemAxon
Polarizability	30.63 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]+	172.888	31661259
DarkChem	[M-H]-	170.599	31661259
DeepCCS	[M+H]+	181.493	30932474
DeepCCS	[M-H]-	179.135	30932474
DeepCCS	[M-2H]-	212.791	30932474
DeepCCS	[M+Na]+	188.018	30932474
AllCCS	[M+H]+	169.8	32859911
AllCCS	[M+H-H2O]+	166.4	32859911
AllCCS	[M+NH4]+	173.0	32859911
AllCCS	[M+Na]+	173.9	32859911
AllCCS	[M-H]-	172.5	32859911
AllCCS	[M+Na-2H]-	171.8	32859911
AllCCS	[M+HCOO]-	171.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid	COC1=C(C(O)=O)C(C)=C2C(=O)C3=C(C=CC=C3O)C(=O)C2=C1	4185.8	Standard polar	33892256
8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid	COC1=C(C(O)=O)C(C)=C2C(=O)C3=C(C=CC=C3O)C(=O)C2=C1	2324.2	Standard non polar	33892256
8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid	COC1=C(C(O)=O)C(C)=C2C(=O)C3=C(C=CC=C3O)C(=O)C2=C1	2900.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid,1TMS,isomer #1	COC1=CC2=C(C(=O)C3=C(O)C=CC=C3C2=O)C(C)=C1C(=O)O[Si](C)(C)C	2843.0	Semi standard non polar	33892256
8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid,1TMS,isomer #2	COC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C2=O)C(C)=C1C(=O)O	2825.1	Semi standard non polar	33892256
8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid,2TMS,isomer #1	COC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C)C=CC=C3C2=O)C(C)=C1C(=O)O[Si](C)(C)C	2856.0	Semi standard non polar	33892256
8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid,1TBDMS,isomer #1	COC1=CC2=C(C(=O)C3=C(O)C=CC=C3C2=O)C(C)=C1C(=O)O[Si](C)(C)C(C)(C)C	3043.7	Semi standard non polar	33892256
8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid,1TBDMS,isomer #2	COC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC=C3C2=O)C(C)=C1C(=O)O	3076.0	Semi standard non polar	33892256
8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid,2TBDMS,isomer #1	COC1=CC2=C(C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC=C3C2=O)C(C)=C1C(=O)O[Si](C)(C)C(C)(C)C	3301.0	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 - 8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-0790000000-a3fa85afe6b6deff30ce	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00uf-6638900000-1bace85883d1afc4aa68	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid 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 - 8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid 10V, Positive-QTOF	splash10-03di-0049000000-89b43999eb20915114ac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid 20V, Positive-QTOF	splash10-01ot-0094000000-e12ccfb87e1e4444a5a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid 40V, Positive-QTOF	splash10-015i-1090000000-70c0189fa3c1ddc09b83	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid 10V, Negative-QTOF	splash10-03xr-0079000000-da1dc15e2a25c208fef7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid 20V, Negative-QTOF	splash10-014i-0091000000-eb19aed2e9b94ee75144	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid 40V, Negative-QTOF	splash10-00kr-1090000000-d2a6fee4face7211aefd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid 10V, Negative-QTOF	splash10-03di-0039000000-d9489d239af27a5ffb6a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid 20V, Negative-QTOF	splash10-03xr-0089000000-67b89d64e3c3dd73e147	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid 40V, Negative-QTOF	splash10-000i-0090000000-abe689e35352134946eb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid 10V, Positive-QTOF	splash10-01ot-0098000000-de5c5cf4e2790e3fb06e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid 20V, Positive-QTOF	splash10-0002-0090000000-9c9b51175bc09ed4b607	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid 40V, Positive-QTOF	splash10-0401-1390000000-2fa1973cba9b7505c52c	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016091

KNApSAcK ID

Not Available

Chemspider ID

30777178

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101991634

PDB ID

Not Available

ChEBI ID

174248

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1859171

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 8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid (HMDB0037101)

MOL for HMDB0037101 (8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid)

3D MOL for HMDB0037101 (8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid)

3D SDF for HMDB0037101 (8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid)

3D-SDF for HMDB0037101 (8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid)

PDB for HMDB0037101 (8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid)

3D PDB for HMDB0037101 (8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid)

SMILES for HMDB0037101 (8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid)

INCHI for HMDB0037101 (8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid)

Structure for HMDB0037101 (8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid)

3D Structure for HMDB0037101 (8-Hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra