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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

HMDB0030830

Secondary Accession Numbers

HMDB30830

Metabolite Identification

Common Name

3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid

Description

3,8-Dihydroxy-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. 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid has been detected, but not quantified in, saffrons (Crocus sativus). This could make 3,8-dihydroxy-1-methylanthraquinone-2-carboxylic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid.

Structure

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

HMDB0030830
     RDKit          3D
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid
 32 34  0  0  0  0  0  0  0  0999 V2000
    1.9750    1.7854    0.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7887    0.5041    0.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8636   -0.2380   -0.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2482    0.1256   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1235   -0.6761   -0.5985 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7557    1.2366    0.4838 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5432   -1.4399   -0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6287   -2.1989   -1.3870 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2563   -1.8666   -1.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875   -1.1268   -0.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4663    0.0584   -0.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6636    0.8409    0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4875    1.9357    1.0648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0596    0.3929    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0847    1.2011    0.7448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7986    2.3890    1.3971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3705    0.7504    0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6140   -0.4320   -0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5934   -1.2026   -0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2793   -0.7884   -0.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1811   -1.6050   -0.8845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3732   -2.6887   -1.4820 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5365    1.6918    1.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0111    2.0608    1.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5137    2.6206    0.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2291    1.2018    1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4530   -3.0719   -1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706   -2.8149   -1.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5914    2.9330    1.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1917    1.3443    0.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6263   -0.7737   -0.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7357   -2.1490   -1.1001 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
  4  6  1  0
  3  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 11  2  1  0
 20 14  1  0
 21 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
M  END


  Mrv0541 05061305322D          

 22 24  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
   -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
    4.2868    0.0000    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
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  1  1  0  0  0  0
  7  3  1  0  0  0  0
  8  5  2  0  0  0  0
  9  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  2  0  0  0  0
 13  7  2  0  0  0  0
 13  9  1  0  0  0  0
 14  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 12  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 14  2  0  0  0  0
 20 15  2  0  0  0  0
 21 16  2  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030830

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2C(=O)C3=C(C=CC=C3O)C(=O)C2=CC(O)=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O6/c1-6-11-8(5-10(18)12(6)16(21)22)14(19)7-3-2-4-9(17)13(7)15(11)20/h2-5,17-18H,1H3,(H,21,22)

> <INCHI_KEY>
MHABMANUFPZXEB-UHFFFAOYSA-N

> <FORMULA>
C16H10O6

> <MOLECULAR_WEIGHT>
298.247

> <EXACT_MASS>
298.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
28.566830184834107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
3.7825797286666667

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.359698600588086

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2268323426401606

> <JCHEM_PKA_STRONGEST_BASIC>
-4.444766738132524

> <JCHEM_POLAR_SURFACE_AREA>
111.89999999999999

> <JCHEM_REFRACTIVITY>
77.41019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030830
     RDKit          3D
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid
 32 34  0  0  0  0  0  0  0  0999 V2000
    1.9750    1.7854    0.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7887    0.5041    0.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8636   -0.2380   -0.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2482    0.1256   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1235   -0.6761   -0.5985 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7557    1.2366    0.4838 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5432   -1.4399   -0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6287   -2.1989   -1.3870 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2563   -1.8666   -1.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875   -1.1268   -0.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4663    0.0584   -0.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6636    0.8409    0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4875    1.9357    1.0648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0596    0.3929    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0847    1.2011    0.7448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7986    2.3890    1.3971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3705    0.7504    0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6140   -0.4320   -0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5934   -1.2026   -0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2793   -0.7884   -0.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1811   -1.6050   -0.8845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3732   -2.6887   -1.4820 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5365    1.6918    1.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0111    2.0608    1.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5137    2.6206    0.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2291    1.2018    1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4530   -3.0719   -1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706   -2.8149   -1.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5914    2.9330    1.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1917    1.3443    0.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6263   -0.7737   -0.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7357   -2.1490   -1.1001 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
  4  6  1  0
  3  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 11  2  1  0
 20 14  1  0
 21 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002   0.000   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
CONECT    1    6                                                            
CONECT    2    3    4                                                       
CONECT    3    2    7                                                       
CONECT    4    2    9                                                       
CONECT    5    8   10                                                       
CONECT    6    1   11   12                                                  
CONECT    7    3   13   14                                                  
CONECT    8    5   11   14                                                  
CONECT    9    4   13   17                                                  
CONECT   10    5   12   18                                                  
CONECT   11    6    8   15                                                  
CONECT   12    6   10   16                                                  
CONECT   13    7    9   15                                                  
CONECT   14    7    8   19                                                  
CONECT   15   11   13   20                                                  
CONECT   16   12   21   22                                                  
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22   16                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0030830
HETATM    1  C1  UNL     1       1.975   1.785   0.904  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.789   0.504   0.188  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.864  -0.238  -0.265  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.248   0.126  -0.116  1.00  0.00           C  
HETATM    5  O1  UNL     1       5.123  -0.676  -0.599  1.00  0.00           O  
HETATM    6  O2  UNL     1       4.756   1.237   0.484  1.00  0.00           O  
HETATM    7  C5  UNL     1       2.543  -1.440  -0.924  1.00  0.00           C  
HETATM    8  O3  UNL     1       3.629  -2.199  -1.387  1.00  0.00           O  
HETATM    9  C6  UNL     1       1.256  -1.867  -1.116  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.188  -1.127  -0.665  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.466   0.058  -0.014  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.664   0.841   0.461  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.488   1.936   1.065  1.00  0.00           O  
HETATM   14  C10 UNL     1      -2.060   0.393   0.259  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.085   1.201   0.745  1.00  0.00           C  
HETATM   16  O5  UNL     1      -2.799   2.389   1.397  1.00  0.00           O  
HETATM   17  C12 UNL     1      -4.370   0.750   0.538  1.00  0.00           C  
HETATM   18  C13 UNL     1      -4.614  -0.432  -0.113  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.593  -1.203  -0.578  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.279  -0.788  -0.392  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.181  -1.605  -0.885  1.00  0.00           C  
HETATM   22  O6  UNL     1      -1.373  -2.689  -1.482  1.00  0.00           O  
HETATM   23  H1  UNL     1       1.537   1.692   1.945  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.011   2.061   1.076  1.00  0.00           H  
HETATM   25  H3  UNL     1       1.514   2.621   0.326  1.00  0.00           H  
HETATM   26  H4  UNL     1       5.229   1.202   1.398  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.453  -3.072  -1.868  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.071  -2.815  -1.638  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.591   2.933   1.727  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.192   1.344   0.897  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.626  -0.774  -0.269  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.736  -2.149  -1.100  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3   11
CONECT    3    4    7
CONECT    4    5    5    6
CONECT    6   26
CONECT    7    8    9    9
CONECT    8   27
CONECT    9   10   28
CONECT   10   11   11   21
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   15   20
CONECT   15   16   17
CONECT   16   29
CONECT   17   18   18   30
CONECT   18   19   31
CONECT   19   20   20   32
CONECT   20   21
CONECT   21   22   22
END

HMDB0030830
     RDKit          3D
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid
 32 34  0  0  0  0  0  0  0  0999 V2000
    1.9750    1.7854    0.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7887    0.5041    0.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8636   -0.2380   -0.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2482    0.1256   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1235   -0.6761   -0.5985 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7557    1.2366    0.4838 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5432   -1.4399   -0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6287   -2.1989   -1.3870 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2563   -1.8666   -1.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875   -1.1268   -0.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4663    0.0584   -0.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6636    0.8409    0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4875    1.9357    1.0648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0596    0.3929    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0847    1.2011    0.7448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7986    2.3890    1.3971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3705    0.7504    0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6140   -0.4320   -0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5934   -1.2026   -0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2793   -0.7884   -0.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1811   -1.6050   -0.8845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3732   -2.6887   -1.4820 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5365    1.6918    1.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0111    2.0608    1.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5137    2.6206    0.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2291    1.2018    1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4530   -3.0719   -1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706   -2.8149   -1.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5914    2.9330    1.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1917    1.3443    0.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6263   -0.7737   -0.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7357   -2.1490   -1.1001 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
  4  6  1  0
  3  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 11  2  1  0
 20 14  1  0
 21 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylate	Generator
9,10-dihydro-3,8-Dihydroxy-1-methyl-9,10-dioxo-2-anthracenecarboxylic acid, 9ci	HMDB
3,8-Dihydroxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate	Generator
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid	MeSH
DMAC-3,8	MeSH
3,8-Dihydroxymethylanthraquinone carboxylic acid	MeSH

Chemical Formula

C₁₆H₁₀O₆

Average Molecular Weight

298.247

Monoisotopic Molecular Weight

298.047738052

IUPAC Name

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

Traditional Name

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

CAS Registry Number

69119-31-9

SMILES

CC1=C2C(=O)C3=C(C=CC=C3O)C(=O)C2=CC(O)=C1C(O)=O

InChI Identifier

InChI=1S/C16H10O6/c1-6-11-8(5-10(18)12(6)16(21)22)14(19)7-3-2-4-9(17)13(7)15(11)20/h2-5,17-18H,1H3,(H,21,22)

InChI Key

MHABMANUFPZXEB-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
Hydroxyanthraquinone
2-naphthalenecarboxylic acid or derivatives
2-naphthalenecarboxylic acid
Salicylic acid or derivatives
Hydroxybenzoic acid
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
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: HMDB0030830)
Cytoplasm (HMDB: HMDB0030830)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030830)

Source

Endogenous

Endogenous (HMDB: HMDB0030830)

Plant

Plant (HMDB: HMDB0030830)

Exogenous

Food

Food (HMDB: HMDB0030830)

Herb and spice

Spice

Saffron (FooDB: FOOD00063)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	248 - 250 °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	0.16 g/L	ALOGPS
logP	2.27	ALOGPS
logP	3.78	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	2.23	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.41 m³·mol⁻¹	ChemAxon
Polarizability	28.57 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]+	167.186	31661259
DarkChem	[M-H]-	169.271	31661259
DeepCCS	[M+H]+	174.415	30932474
DeepCCS	[M-H]-	172.057	30932474
DeepCCS	[M-2H]-	205.295	30932474
DeepCCS	[M+Na]+	180.522	30932474
AllCCS	[M+H]+	166.0	32859911
AllCCS	[M+H-H2O]+	162.5	32859911
AllCCS	[M+NH4]+	169.3	32859911
AllCCS	[M+Na]+	170.3	32859911
AllCCS	[M-H]-	167.3	32859911
AllCCS	[M+Na-2H]-	166.5	32859911
AllCCS	[M+HCOO]-	165.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid	CC1=C2C(=O)C3=C(C=CC=C3O)C(=O)C2=CC(O)=C1C(O)=O	4056.1	Standard polar	33892256
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid	CC1=C2C(=O)C3=C(C=CC=C3O)C(=O)C2=CC(O)=C1C(O)=O	2044.2	Standard non polar	33892256
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid	CC1=C2C(=O)C3=C(C=CC=C3O)C(=O)C2=CC(O)=C1C(O)=O	2720.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid,1TMS,isomer #1	CC1=C(C(=O)O)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1C2=O	2799.6	Semi standard non polar	33892256
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid,1TMS,isomer #2	CC1=C(C(=O)O)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O)C=CC=C1C2=O	2771.3	Semi standard non polar	33892256
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid,1TMS,isomer #3	CC1=C(C(=O)O[Si](C)(C)C)C(O)=CC2=C1C(=O)C1=C(O)C=CC=C1C2=O	2852.8	Semi standard non polar	33892256
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid,2TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1C2=O	2862.5	Semi standard non polar	33892256
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid,2TMS,isomer #2	CC1=C(C(=O)O)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1C2=O	2808.6	Semi standard non polar	33892256
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid,2TMS,isomer #3	CC1=C(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O)C=CC=C1C2=O	2807.2	Semi standard non polar	33892256
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid,3TMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1C2=O	2858.5	Semi standard non polar	33892256
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid,1TBDMS,isomer #1	CC1=C(C(=O)O)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1C2=O	3066.0	Semi standard non polar	33892256
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid,1TBDMS,isomer #2	CC1=C(C(=O)O)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O)C=CC=C1C2=O	3017.6	Semi standard non polar	33892256
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid,1TBDMS,isomer #3	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O)=CC2=C1C(=O)C1=C(O)C=CC=C1C2=O	3075.0	Semi standard non polar	33892256
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid,2TBDMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1C2=O	3315.1	Semi standard non polar	33892256
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid,2TBDMS,isomer #2	CC1=C(C(=O)O)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1C2=O	3259.6	Semi standard non polar	33892256
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid,2TBDMS,isomer #3	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O)C=CC=C1C2=O	3233.3	Semi standard non polar	33892256
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid,3TBDMS,isomer #1	CC1=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1C2=O	3493.1	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 - 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fir-0490000000-125a9b2d8ba2e52ead02	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid GC-MS (3 TMS) - 70eV, Positive	splash10-00dv-6203910000-d048503afe44baea50b6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,8-Dihydroxy-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 - 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid 10V, Positive-QTOF	splash10-0002-0090000000-4031c6b271db004a5a40	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid 20V, Positive-QTOF	splash10-001j-0090000000-2b96f4544e6255b71ffc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid 40V, Positive-QTOF	splash10-0019-2090000000-cc3c1d000960bbd7f1fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid 10V, Negative-QTOF	splash10-0f6t-0090000000-8eed3311a06a79a4ee91	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid 20V, Negative-QTOF	splash10-0udi-0090000000-ea32876963f7732a65cd	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid 40V, Negative-QTOF	splash10-0udi-1090000000-da28f58982d0c3ae4e75	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid 10V, Positive-QTOF	splash10-001j-0090000000-4b231a8cd56f86d5ee83	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid 20V, Positive-QTOF	splash10-001i-0090000000-a1af9499e0121d9c7efe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid 40V, Positive-QTOF	splash10-03di-0390000000-17eb57f61753259990f8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid 10V, Negative-QTOF	splash10-0f6t-0090000000-ff57c6adc82fbe6db529	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid 20V, Negative-QTOF	splash10-0udi-0090000000-941f00f78ae70af18204	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid 40V, Negative-QTOF	splash10-0ufr-0090000000-7345e0ee16c974005862	2021-09-23	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

FDB002786

KNApSAcK ID

C00055494

Chemspider ID

11297920

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14379528

PDB ID

Not Available

ChEBI ID

174833

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 3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid (HMDB0030830)

MOL for HMDB0030830 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)

3D MOL for HMDB0030830 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)

3D SDF for HMDB0030830 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)

3D-SDF for HMDB0030830 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)

PDB for HMDB0030830 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)

3D PDB for HMDB0030830 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)

SMILES for HMDB0030830 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)

INCHI for HMDB0030830 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)

Structure for HMDB0030830 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)

3D Structure for HMDB0030830 (3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra