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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:31 UTC

Update Date

2022-03-07 02:52:44 UTC

HMDB ID

HMDB0030871

Secondary Accession Numbers

HMDB30871

Metabolite Identification

Common Name

Isogentisin

Description

Isogentisin belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. Isogentisin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Isogentisin.

Structure

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

HMDB0030871
     RDKit          3D
Isogentisin
 29 31  0  0  0  0  0  0  0  0999 V2000
    4.8492    0.2304    0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3988   -0.8119   -0.0663 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0362   -0.8918   -0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5429   -1.8741   -1.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1984   -1.9818   -1.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2720   -1.0945   -0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0024   -1.1982   -1.1279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8962   -0.3906   -0.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2203   -0.5749   -0.9558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1363    0.2929   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4961    0.1234   -0.7335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7759    1.3105    0.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4228    1.5134    0.7806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0903    2.5312    1.6190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5032    0.6390    0.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1496    0.7614    0.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2927    1.6372    1.2596 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630   -0.1131   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1235   -0.0168    0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9589    0.1968    0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5113    0.0728    1.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5364    1.2195    0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2759   -2.5695   -1.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8117   -2.7572   -2.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5461   -1.3766   -1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0199   -0.4853   -0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5153    1.9858    0.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2677    2.8560    1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4710    0.7658    0.8889 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
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19  3  1  0
 18  6  1  0
 15  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 19 29  1  0
M  END


  Mrv1652309272007352D          

 19 21  0  0  0  0            999 V2000
 9998.4172 9997.5506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5576 9998.3755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8457 9997.5506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.274810000.0254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.845610000.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8456 9998.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5600 9998.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5600 9999.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.987110000.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2726 9999.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2726 9998.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9869 9998.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.416710000.0254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7023 9999.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7023 9998.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4167 9998.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1311 9998.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1311 9999.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.8434 9998.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  5  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  8  4  1  0  0  0  0
  6  3  1  0  0  0  0
 11  2  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
  1 16  2  0  0  0  0
  5 18  2  0  0  0  0
 17  6  2  0  0  0  0
 14  9  2  0  0  0  0
 12 15  2  0  0  0  0
  2 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030871

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C2OC3=CC(O)=CC(O)=C3C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O5/c1-18-8-2-3-11-9(6-8)14(17)13-10(16)4-7(15)5-12(13)19-11/h2-6,15-16H,1H3

> <INCHI_KEY>
FVIYCYAHKMJVJK-UHFFFAOYSA-N

> <FORMULA>
C14H10O5

> <MOLECULAR_WEIGHT>
258.2262

> <EXACT_MASS>
258.05282343

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.384539952934166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-dihydroxy-7-methoxy-9H-xanthen-9-one

> <ALOGPS_LOGP>
2.84

> <JCHEM_LOGP>
2.844838311333333

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.14765311809924

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.547897263384937

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7241158454274452

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
67.24130000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isogentisin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030871
     RDKit          3D
Isogentisin
 29 31  0  0  0  0  0  0  0  0999 V2000
    4.8492    0.2304    0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3988   -0.8119   -0.0663 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0362   -0.8918   -0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5429   -1.8741   -1.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1984   -1.9818   -1.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2720   -1.0945   -0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0024   -1.1982   -1.1279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8962   -0.3906   -0.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2203   -0.5749   -0.9558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1363    0.2929   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4961    0.1234   -0.7335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7759    1.3105    0.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4228    1.5134    0.7806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0903    2.5312    1.6190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5032    0.6390    0.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1496    0.7614    0.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2927    1.6372    1.2596 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630   -0.1131   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1235   -0.0168    0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9589    0.1968    0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5113    0.0728    1.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5364    1.2195    0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2759   -2.5695   -1.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8117   -2.7572   -2.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5461   -1.3766   -1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0199   -0.4853   -0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5153    1.9858    0.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2677    2.8560    1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4710    0.7658    0.8889 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
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19  3  1  0
 18  6  1  0
 15  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 19 29  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8663.7128662.094   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8658.3748663.634   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8666.3798662.094   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8669.0468666.714   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8666.3788666.714   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8666.3788663.634   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8667.7128664.404   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8667.7128665.944   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8661.0438666.714   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8659.7098665.944   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8659.7098664.404   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.0428663.634   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8663.7118666.714   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8662.3788665.944   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8662.3788664.404   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.7118663.634   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.0458664.404   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.0458665.944   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8657.0418664.405   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2   11   19                                                       
CONECT    3    6                                                            
CONECT    4    8                                                            
CONECT    5    8   18                                                       
CONECT    6    7    3   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    5    4                                                  
CONECT    9   10   14                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    2                                                  
CONECT   12   11   15                                                       
CONECT   13   14   18                                                       
CONECT   14   15   13    9                                                  
CONECT   15   14   16   12                                                  
CONECT   16   15   17    1                                                  
CONECT   17   16   18    6                                                  
CONECT   18   17   13    5                                                  
CONECT   19    2                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0030871
HETATM    1  C1  UNL     1       4.849   0.230   0.808  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.399  -0.812  -0.066  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.036  -0.892  -0.320  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.543  -1.874  -1.154  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.198  -1.982  -1.427  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.272  -1.095  -0.868  1.00  0.00           C  
HETATM    7  O2  UNL     1      -1.002  -1.198  -1.128  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.896  -0.391  -0.626  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.220  -0.575  -0.956  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.136   0.293  -0.410  1.00  0.00           C  
HETATM   11  O3  UNL     1      -5.496   0.123  -0.734  1.00  0.00           O  
HETATM   12  C9  UNL     1      -3.776   1.311   0.432  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.423   1.513   0.781  1.00  0.00           C  
HETATM   14  O4  UNL     1      -2.090   2.531   1.619  1.00  0.00           O  
HETATM   15  C11 UNL     1      -1.503   0.639   0.230  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.150   0.761   0.516  1.00  0.00           C  
HETATM   17  O5  UNL     1       0.293   1.637   1.260  1.00  0.00           O  
HETATM   18  C13 UNL     1       0.763  -0.113  -0.035  1.00  0.00           C  
HETATM   19  C14 UNL     1       2.124  -0.017   0.231  1.00  0.00           C  
HETATM   20  H1  UNL     1       5.959   0.197   0.774  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.511   0.073   1.843  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.536   1.219   0.415  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.276  -2.569  -1.591  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.812  -2.757  -2.085  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.546  -1.377  -1.625  1.00  0.00           H  
HETATM   26  H7  UNL     1      -6.020  -0.485  -0.119  1.00  0.00           H  
HETATM   27  H8  UNL     1      -4.515   1.986   0.853  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.268   2.856   1.987  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.471   0.766   0.889  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   23
CONECT    5    6    6   24
CONECT    6    7   18
CONECT    7    8
CONECT    8    9    9   15
CONECT    9   10   25
CONECT   10   11   12   12
CONECT   11   26
CONECT   12   13   27
CONECT   13   14   15   15
CONECT   14   28
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19   19
CONECT   19   29
END

HMDB0030871
     RDKit          3D
Isogentisin
 29 31  0  0  0  0  0  0  0  0999 V2000
    4.8492    0.2304    0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3988   -0.8119   -0.0663 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0362   -0.8918   -0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5429   -1.8741   -1.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1984   -1.9818   -1.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2720   -1.0945   -0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0024   -1.1982   -1.1279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8962   -0.3906   -0.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2203   -0.5749   -0.9558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1363    0.2929   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4961    0.1234   -0.7335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7759    1.3105    0.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4228    1.5134    0.7806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0903    2.5312    1.6190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5032    0.6390    0.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1496    0.7614    0.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2927    1.6372    1.2596 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630   -0.1131   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1235   -0.0168    0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9589    0.1968    0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5113    0.0728    1.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5364    1.2195    0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2759   -2.5695   -1.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8117   -2.7572   -2.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5461   -1.3766   -1.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0199   -0.4853   -0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5153    1.9858    0.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2677    2.8560    1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4710    0.7658    0.8889 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
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19  3  1  0
 18  6  1  0
 15  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 19 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,3-Dihydroxy--7-methoxyxanthone	ChEBI
Isogentisine	ChEBI
1,3-Dihydroxy-7-methoxyxanthone	HMDB
1,3-Dihydroxy-7-methoxy-xanthone	HMDB
Iso-gentisin	HMDB
1,3-Dihydroxy-7-methoxy-9H-xanthen-9-one	HMDB
1,3-Dihydroxy-7-methoxy-xanthen-9-one	HMDB
1,3-Dihydroxy-7-methoxyxanthen-9-one	HMDB
9H-Xanthen-9-one, 1,3-dihydroxy-7-methoxy- (9ci)	HMDB

Chemical Formula

C₁₄H₁₀O₅

Average Molecular Weight

258.2262

Monoisotopic Molecular Weight

258.05282343

IUPAC Name

1,3-dihydroxy-7-methoxy-9H-xanthen-9-one

Traditional Name

isogentisin

CAS Registry Number

491-64-5

SMILES

COC1=CC2=C(OC3=CC(O)=CC(O)=C3C2=O)C=C1

InChI Identifier

InChI=1S/C14H10O5/c1-18-8-2-3-11-9(6-8)14(17)13-10(16)4-7(15)5-12(13)19-11/h2-6,15-16H,1H3

InChI Key

FVIYCYAHKMJVJK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Chromone
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:6017 )
polyphenol (CHEBI:6017 )
xanthones (CHEBI:6017 )
xanthenes (C10070 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030871)

Cellular substructure

Membrane (HMDB: HMDB0030871)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030871)

Source

Endogenous

Endogenous (HMDB: HMDB0030871)

Plant

Plant (HMDB: HMDB0030871)

Exogenous

Food

Food (HMDB: HMDB0030871)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	241 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4.02 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	0.23 g/L	ALOGPS
logP	2.84	ALOGPS
logP	2.84	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.55	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.24 m³·mol⁻¹	ChemAxon
Polarizability	25.38 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]+	159.519	31661259
DarkChem	[M-H]-	161.769	31661259
DeepCCS	[M+H]+	164.219	30932474
DeepCCS	[M-H]-	161.861	30932474
DeepCCS	[M-2H]-	194.747	30932474
DeepCCS	[M+Na]+	170.312	30932474
AllCCS	[M+H]+	156.9	32859911
AllCCS	[M+H-H2O]+	153.0	32859911
AllCCS	[M+NH4]+	160.6	32859911
AllCCS	[M+Na]+	161.7	32859911
AllCCS	[M-H]-	158.9	32859911
AllCCS	[M+Na-2H]-	158.2	32859911
AllCCS	[M+HCOO]-	157.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isogentisin	COC1=CC2=C(OC3=CC(O)=CC(O)=C3C2=O)C=C1	4048.0	Standard polar	33892256
Isogentisin	COC1=CC2=C(OC3=CC(O)=CC(O)=C3C2=O)C=C1	2630.8	Standard non polar	33892256
Isogentisin	COC1=CC2=C(OC3=CC(O)=CC(O)=C3C2=O)C=C1	2670.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isogentisin,1TMS,isomer #1	COC1=CC=C2OC3=CC(O[Si](C)(C)C)=CC(O)=C3C(=O)C2=C1	2794.1	Semi standard non polar	33892256
Isogentisin,1TMS,isomer #2	COC1=CC=C2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C(=O)C2=C1	2764.0	Semi standard non polar	33892256
Isogentisin,2TMS,isomer #1	COC1=CC=C2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C(=O)C2=C1	2865.8	Semi standard non polar	33892256
Isogentisin,1TBDMS,isomer #1	COC1=CC=C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C(=O)C2=C1	3014.0	Semi standard non polar	33892256
Isogentisin,1TBDMS,isomer #2	COC1=CC=C2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C(=O)C2=C1	2988.4	Semi standard non polar	33892256
Isogentisin,2TBDMS,isomer #1	COC1=CC=C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C(=O)C2=C1	3282.0	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 - Isogentisin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1490000000-b56d7cd86d4ece8509d7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isogentisin GC-MS (2 TMS) - 70eV, Positive	splash10-0079-2439000000-c218c67602435a09b248	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isogentisin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isogentisin 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 - Isogentisin 10V, Positive-QTOF	splash10-0a4i-0090000000-a5076a86a77530e5c14e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isogentisin 20V, Positive-QTOF	splash10-0a4i-0090000000-97dc49e24dd400e279e6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isogentisin 40V, Positive-QTOF	splash10-08fu-1190000000-3ec3bc9351f104476ba2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isogentisin 10V, Negative-QTOF	splash10-0a4i-0090000000-32dc1587afbdc73517de	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isogentisin 20V, Negative-QTOF	splash10-0a4i-0090000000-4cb9feddb4c81115de2e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isogentisin 40V, Negative-QTOF	splash10-0a7i-1390000000-a9ba04f3745a953f7783	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isogentisin 10V, Positive-QTOF	splash10-0a4i-0090000000-adb7dbccff647a617461	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isogentisin 20V, Positive-QTOF	splash10-0a4i-0090000000-adb7dbccff647a617461	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isogentisin 40V, Positive-QTOF	splash10-014u-1970000000-a8361d5a92587faaefd8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isogentisin 10V, Negative-QTOF	splash10-0a4i-0090000000-5c99e00473c8f7c5ab03	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isogentisin 20V, Negative-QTOF	splash10-0a4i-0090000000-5c99e00473c8f7c5ab03	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isogentisin 40V, Negative-QTOF	splash10-0fri-1590000000-ecfda9b33d890a224c02	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281640

PDB ID

Not Available

ChEBI ID

6017

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1823311

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 Isogentisin (HMDB0030871)

MOL for HMDB0030871 (Isogentisin)

3D MOL for HMDB0030871 (Isogentisin)

3D SDF for HMDB0030871 (Isogentisin)

3D-SDF for HMDB0030871 (Isogentisin)

PDB for HMDB0030871 (Isogentisin)

3D PDB for HMDB0030871 (Isogentisin)

SMILES for HMDB0030871 (Isogentisin)

INCHI for HMDB0030871 (Isogentisin)

Structure for HMDB0030871 (Isogentisin)

3D Structure for HMDB0030871 (Isogentisin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra