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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:51:05 UTC

Update Date

2021-09-26 22:54:29 UTC

HMDB ID

HMDB0245799

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Alizarinsulfonic acid

Description

3-Alizarinsulfonic acid, also known as alizarin red or az-R, 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. Based on a literature review very few articles have been published on 3-Alizarinsulfonic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3-alizarinsulfonic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3-Alizarinsulfonic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0245799
     RDKit          3D
3-Alizarinsulfonic acid
 30 32  0  0  0  0  0  0  0  0999 V2000
    0.9908   -1.9269    1.7477 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0220   -1.0228    0.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2727   -0.4885    0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4850   -0.9623    0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6830   -0.4722    0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6640    0.5214   -0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4781    1.0251   -1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3046    0.5023   -0.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0074    1.0129   -1.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0486    1.9226   -1.9643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2453    0.4779   -0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2696   -0.5175    0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4476   -1.0487    0.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6606   -0.5830    0.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1803   -1.2161    1.0847 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.9144   -2.2555    2.1357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9281   -1.8165   -0.0822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0921    0.0008    1.8051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513    0.4007   -0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8664    0.8759   -0.9338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4661    0.9529   -1.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5301    1.9212   -1.9518 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4699   -1.7495    1.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6218   -0.8785    0.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6098    0.8967   -0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4404    1.8166   -1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4095   -1.8131    1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5772    0.3442    2.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8728    1.6018   -1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9869    2.4782   -2.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  2  0
 15 18  1  0
 14 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 12  2  1  0
  8  3  1  0
 21 11  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
 13 27  1  0
 18 28  1  0
 20 29  1  0
 22 30  1  0
M  END


  Mrv0541 05041400232D          

 22 24  0  0  0  0            999 V2000
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
    4.2868    2.4750    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
    3.5724    1.2375    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    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    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
    0.0000    2.4750    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
   -0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13  9  2  0  0  0  0
 14 10  2  0  0  0  0
 14 13  1  0  0  0  0
 15 11  2  0  0  0  0
 16 12  2  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 22  9  1  0  0  0  0
 22 19  1  0  0  0  0
 22 20  2  0  0  0  0
 22 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245799

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=C(C=C2C(=O)C3=CC=CC=C3C(=O)C2=C1O)S(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H8O7S/c15-11-6-3-1-2-4-7(6)12(16)10-8(11)5-9(22(19,20)21)13(17)14(10)18/h1-5,17-18H,(H,19,20,21)

> <INCHI_KEY>
JKYKXTRKURYNGW-UHFFFAOYSA-N

> <FORMULA>
C14H8O7S

> <MOLECULAR_WEIGHT>
320.274

> <EXACT_MASS>
319.9990733

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
28.945474880516063

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid

> <ALOGPS_LOGP>
0.54

> <JCHEM_LOGP>
2.7924821479999995

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.83559436554995

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.799507713554969

> <JCHEM_PKA_STRONGEST_BASIC>
-4.856338671098359

> <JCHEM_POLAR_SURFACE_AREA>
128.97

> <JCHEM_REFRACTIVITY>
75.7353

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
alizarin red S

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0245799
     RDKit          3D
3-Alizarinsulfonic acid
 30 32  0  0  0  0  0  0  0  0999 V2000
    0.9908   -1.9269    1.7477 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0220   -1.0228    0.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2727   -0.4885    0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4850   -0.9623    0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6830   -0.4722    0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6640    0.5214   -0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4781    1.0251   -1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3046    0.5023   -0.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0074    1.0129   -1.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0486    1.9226   -1.9643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2453    0.4779   -0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2696   -0.5175    0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4476   -1.0487    0.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6606   -0.5830    0.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1803   -1.2161    1.0847 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.9144   -2.2555    2.1357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9281   -1.8165   -0.0822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0921    0.0008    1.8051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513    0.4007   -0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8664    0.8759   -0.9338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4661    0.9529   -1.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5301    1.9212   -1.9518 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4699   -1.7495    1.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6218   -0.8785    0.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6098    0.8967   -0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4404    1.8166   -1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4095   -1.8131    1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5772    0.3442    2.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8728    1.6018   -1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9869    2.4782   -2.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  2  0
 15 18  1  0
 14 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 12  2  1  0
  8  3  1  0
 21 11  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
 13 27  1  0
 18 28  1  0
 20 29  1  0
 22 30  1  0
M  END

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2    7                                                       
CONECT    5    8    9                                                       
CONECT    6    3    7   11                                                  
CONECT    7    4    6   12                                                  
CONECT    8    5   10   11                                                  
CONECT    9    5   13   22                                                  
CONECT   10    8   12   14                                                  
CONECT   11    6    8   15                                                  
CONECT   12    7   10   16                                                  
CONECT   13    9   14   17                                                  
CONECT   14   10   13   18                                                  
CONECT   15   11                                                            
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18   14                                                            
CONECT   19   22                                                            
CONECT   20   22                                                            
CONECT   21   22                                                            
CONECT   22    9   19   20   21                                             
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0245799
HETATM    1  O1  UNL     1       0.991  -1.927   1.748  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.022  -1.023   0.876  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.273  -0.488   0.355  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.485  -0.962   0.807  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.683  -0.472   0.329  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.664   0.521  -0.629  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.478   1.025  -1.109  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.305   0.502  -0.600  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.007   1.013  -1.087  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.049   1.923  -1.964  1.00  0.00           O  
HETATM   11  C9  UNL     1      -0.245   0.478  -0.566  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.270  -0.518   0.394  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.448  -1.049   0.911  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.661  -0.583   0.468  1.00  0.00           C  
HETATM   15  S1  UNL     1      -4.180  -1.216   1.085  1.00  0.00           S  
HETATM   16  O3  UNL     1      -3.914  -2.255   2.136  1.00  0.00           O  
HETATM   17  O4  UNL     1      -4.928  -1.816  -0.082  1.00  0.00           O  
HETATM   18  O5  UNL     1      -5.092   0.001   1.805  1.00  0.00           O  
HETATM   19  C13 UNL     1      -2.651   0.401  -0.481  1.00  0.00           C  
HETATM   20  O6  UNL     1      -3.866   0.876  -0.934  1.00  0.00           O  
HETATM   21  C14 UNL     1      -1.466   0.953  -1.018  1.00  0.00           C  
HETATM   22  O7  UNL     1      -1.530   1.921  -1.952  1.00  0.00           O  
HETATM   23  H1  UNL     1       3.470  -1.750   1.566  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.622  -0.878   0.717  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.610   0.897  -0.995  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.440   1.817  -1.872  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.409  -1.813   1.648  1.00  0.00           H  
HETATM   28  H6  UNL     1      -4.577   0.344   2.570  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.873   1.602  -1.634  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.987   2.478  -2.491  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4    8
CONECT    4    5   23
CONECT    5    6    6   24
CONECT    6    7   25
CONECT    7    8    8   26
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   21
CONECT   12   13
CONECT   13   14   14   27
CONECT   14   15   19
CONECT   15   16   16   17   17
CONECT   15   18
CONECT   18   28
CONECT   19   20   21   21
CONECT   20   29
CONECT   21   22
CONECT   22   30
END

HMDB0245799
     RDKit          3D
3-Alizarinsulfonic acid
 30 32  0  0  0  0  0  0  0  0999 V2000
    0.9908   -1.9269    1.7477 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0220   -1.0228    0.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2727   -0.4885    0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4850   -0.9623    0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6830   -0.4722    0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6640    0.5214   -0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4781    1.0251   -1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3046    0.5023   -0.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0074    1.0129   -1.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0486    1.9226   -1.9643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2453    0.4779   -0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2696   -0.5175    0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4476   -1.0487    0.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6606   -0.5830    0.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1803   -1.2161    1.0847 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.9144   -2.2555    2.1357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9281   -1.8165   -0.0822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0921    0.0008    1.8051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513    0.4007   -0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8664    0.8759   -0.9338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4661    0.9529   -1.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5301    1.9212   -1.9518 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4699   -1.7495    1.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6218   -0.8785    0.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6098    0.8967   -0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4404    1.8166   -1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4095   -1.8131    1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5772    0.3442    2.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8728    1.6018   -1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9869    2.4782   -2.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  2  0
 15 18  1  0
 14 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 12  2  1  0
  8  3  1  0
 21 11  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
 13 27  1  0
 18 28  1  0
 20 29  1  0
 22 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Dihydroxy-3-sulfoanthraquinone	ChEBI
1,2-Dihydroxy-3-sulfonate-9,10-anthraquinone	ChEBI
3,4-Dihydroxy-2-anthraquinonesulfonic acid	ChEBI
3,4-Dihydroxy-9,10-anthraquinone-2-sulfonic acid	ChEBI
3,4-Dihydroxy-9,10-dioxo-2-anthracenesulfonic acid	ChEBI
9,10-Dihydro-3,4-dihydroxy-9,10-dioxo-2-anthracenesulfonic acid	ChEBI
ALIZARIN red	ChEBI
Alizarin red S	ChEBI
Alizarin red S free acid	ChEBI
Az-R	ChEBI
1,2-Dihydroxy-3-sulphoanthraquinone	Generator
1,2-Dihydroxy-3-sulfonic acid-9,10-anthraquinone	Generator
1,2-Dihydroxy-3-sulphonate-9,10-anthraquinone	Generator
1,2-Dihydroxy-3-sulphonic acid-9,10-anthraquinone	Generator
3,4-Dihydroxy-2-anthraquinonesulfonate	Generator
3,4-Dihydroxy-2-anthraquinonesulphonate	Generator
3,4-Dihydroxy-2-anthraquinonesulphonic acid	Generator
3,4-Dihydroxy-9,10-anthraquinone-2-sulfonate	Generator
3,4-Dihydroxy-9,10-anthraquinone-2-sulphonate	Generator
3,4-Dihydroxy-9,10-anthraquinone-2-sulphonic acid	Generator
3,4-Dihydroxy-9,10-dioxo-2-anthracenesulfonate	Generator
3,4-Dihydroxy-9,10-dioxo-2-anthracenesulphonate	Generator
3,4-Dihydroxy-9,10-dioxo-2-anthracenesulphonic acid	Generator
9,10-Dihydro-3,4-dihydroxy-9,10-dioxo-2-anthracenesulfonate	Generator
9,10-Dihydro-3,4-dihydroxy-9,10-dioxo-2-anthracenesulphonate	Generator
9,10-Dihydro-3,4-dihydroxy-9,10-dioxo-2-anthracenesulphonic acid	Generator
3-Alizarinsulfonate	Generator
3-Alizarinsulphonate	Generator
3-Alizarinsulphonic acid	Generator
3,4-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate	HMDB
3,4-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulphonate	HMDB
3,4-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulphonic acid	HMDB
Alizarin red S, monosodium salt	HMDB
Alizarine S	HMDB
Alizarine sulfonate	HMDB
3-Alizarinsulfonic acid	ChEBI

Chemical Formula

C₁₄H₈O₇S

Average Molecular Weight

320.274

Monoisotopic Molecular Weight

319.9990733

IUPAC Name

3,4-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid

Traditional Name

alizarin red S

CAS Registry Number

Not Available

SMILES

OC1=C(C=C2C(=O)C3=CC=CC=C3C(=O)C2=C1O)S(O)(=O)=O

InChI Identifier

InChI=1S/C14H8O7S/c15-11-6-3-1-2-4-7(6)12(16)10-8(11)5-9(22(19,20)21)13(17)14(10)18/h1-5,17-18H,(H,19,20,21)

InChI Key

JKYKXTRKURYNGW-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
Arylsulfonic acid or derivatives
1-sulfo,2-unsubstituted aromatic compound
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Vinylogous acid
Ketone
Organosulfur compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

organosulfonic acid (CHEBI:40863 )
dihydroxyanthraquinone (CHEBI:40863 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.54	ALOGPS
logP	2.79	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	-2.8	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	128.97 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.74 m³·mol⁻¹	ChemAxon
Polarizability	28.95 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
DeepCCS	[M+H]+	171.602	30932474
DeepCCS	[M-H]-	169.244	30932474
DeepCCS	[M-2H]-	202.389	30932474
DeepCCS	[M+Na]+	177.695	30932474
AllCCS	[M+H]+	169.0	32859911
AllCCS	[M+H-H2O]+	165.6	32859911
AllCCS	[M+NH4]+	172.2	32859911
AllCCS	[M+Na]+	173.1	32859911
AllCCS	[M-H]-	164.5	32859911
AllCCS	[M+Na-2H]-	163.8	32859911
AllCCS	[M+HCOO]-	163.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.3892 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.1 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1678.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	252.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	106.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	84.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	412.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	475.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	595.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	711.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	312.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1086.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	257.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	258.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	393.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	279.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	318.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Alizarinsulfonic acid	OC1=C(C=C2C(=O)C3=CC=CC=C3C(=O)C2=C1O)S(O)(=O)=O	4645.3	Standard polar	33892256
3-Alizarinsulfonic acid	OC1=C(C=C2C(=O)C3=CC=CC=C3C(=O)C2=C1O)S(O)(=O)=O	1749.1	Standard non polar	33892256
3-Alizarinsulfonic acid	OC1=C(C=C2C(=O)C3=CC=CC=C3C(=O)C2=C1O)S(O)(=O)=O	2967.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Alizarinsulfonic acid,3TMS,isomer #1	C[Si](C)(C)OC1=C(S(=O)(=O)O[Si](C)(C)C)C=C2C(=O)C3=CC=CC=C3C(=O)C2=C1O[Si](C)(C)C	2923.6	Semi standard non polar	33892256
3-Alizarinsulfonic acid,3TMS,isomer #1	C[Si](C)(C)OC1=C(S(=O)(=O)O[Si](C)(C)C)C=C2C(=O)C3=CC=CC=C3C(=O)C2=C1O[Si](C)(C)C	3262.5	Standard non polar	33892256
3-Alizarinsulfonic acid,3TMS,isomer #1	C[Si](C)(C)OC1=C(S(=O)(=O)O[Si](C)(C)C)C=C2C(=O)C3=CC=CC=C3C(=O)C2=C1O[Si](C)(C)C	3559.2	Standard polar	33892256
3-Alizarinsulfonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(S(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C2C(=O)C3=CC=CC=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C	3550.9	Semi standard non polar	33892256
3-Alizarinsulfonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(S(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C2C(=O)C3=CC=CC=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C	4038.2	Standard non polar	33892256
3-Alizarinsulfonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(S(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C2C(=O)C3=CC=CC=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C	3729.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Alizarinsulfonic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-0292000000-949845478524b23b949f	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Alizarinsulfonic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Alizarinsulfonic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Alizarinsulfonic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Alizarinsulfonic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Alizarinsulfonic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Alizarinsulfonic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Alizarinsulfonic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Alizarinsulfonic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Alizarinsulfonic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Alizarinsulfonic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Alizarinsulfonic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Alizarinsulfonic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Alizarinsulfonic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	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-Alizarinsulfonic acid 10V, Positive-QTOF	splash10-00di-0009000000-56f02a856283f4e8482b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Alizarinsulfonic acid 20V, Positive-QTOF	splash10-00di-0019000000-26923ca837b97220f617	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Alizarinsulfonic acid 40V, Positive-QTOF	splash10-0a4j-1910000000-78a1e84c867b87fc66f5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Alizarinsulfonic acid 10V, Negative-QTOF	splash10-014i-0009000000-a7a84e1cf927a4727896	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Alizarinsulfonic acid 20V, Negative-QTOF	splash10-014i-3029000000-06c30707514d6f1a4199	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Alizarinsulfonic acid 40V, Negative-QTOF	splash10-053i-0290000000-087d5d9ccc97d9c373d4	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8218

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8534

PDB ID

Not Available

ChEBI ID

40863

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 3-Alizarinsulfonic acid (HMDB0245799)

MOL for HMDB0245799 (3-Alizarinsulfonic acid)

3D MOL for HMDB0245799 (3-Alizarinsulfonic acid)

3D SDF for HMDB0245799 (3-Alizarinsulfonic acid)

3D-SDF for HMDB0245799 (3-Alizarinsulfonic acid)

PDB for HMDB0245799 (3-Alizarinsulfonic acid)

3D PDB for HMDB0245799 (3-Alizarinsulfonic acid)

SMILES for HMDB0245799 (3-Alizarinsulfonic acid)

INCHI for HMDB0245799 (3-Alizarinsulfonic acid)

Structure for HMDB0245799 (3-Alizarinsulfonic acid)

3D Structure for HMDB0245799 (3-Alizarinsulfonic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra