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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:35:04 UTC

Update Date

2021-09-26 22:52:09 UTC

HMDB ID

HMDB0244424

Secondary Accession Numbers

None

Metabolite Identification

Common Name

8-Methylxanthen-9-one-4-acetic acid

Description

117570-76-0 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. Based on a literature review very few articles have been published on 117570-76-0. This compound has been identified in human blood as reported by (PMID: 31557052 ). 8-methylxanthen-9-one-4-acetic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 8-Methylxanthen-9-one-4-acetic 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

HMDB0244424
     RDKit          3D
8-Methylxanthen-9-one-4-acetic acid
 32 34  0  0  0  0  0  0  0  0999 V2000
    4.0910    0.3236    0.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8612    1.1296   -0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9389    2.4925   -0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8226    3.2675   -0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5966    2.6226   -0.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4640    1.2643   -0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7033    0.6570   -0.2991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8262   -0.6320   -0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0692   -1.2172   -0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2588   -0.3649   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6758    0.3670    0.8480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0461    0.2298    1.9152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7710    1.2034    0.7936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2128   -2.5839    0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1233   -3.3994    0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1221   -2.8049    0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2863   -1.4510    0.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5353   -0.8490    0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5239   -1.5763    0.3620 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6223    0.5103   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0931   -0.1252    1.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2564   -0.3543   -0.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9571    1.0499    0.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9084    2.9913   -0.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8951    4.3551   -0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2858    3.2336   -0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1125    0.3500   -1.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0960   -1.0394   -0.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3846    1.2735   -0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1980   -3.0597    0.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2231   -4.4735    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0122   -3.3903    0.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  9 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20  2  1  0
 20  6  2  0
 17  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
M  END


  Mrv1652309102123352D          

 20 22  0  0  0  0            999 V2000
    3.5724   -1.2375    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
    2.8579   -0.0000    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   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
    1.4289    0.0000    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
    2.1434   -1.2375    0.0000 O   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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244424

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2C(=O)C3=C(OC2=CC=C1)C(CC(O)=O)=CC=C3

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O4/c1-9-4-2-7-12-14(9)15(19)11-6-3-5-10(8-13(17)18)16(11)20-12/h2-7H,8H2,1H3,(H,17,18)

> <INCHI_KEY>
LOMULPZJAGQWGF-UHFFFAOYSA-N

> <FORMULA>
C16H12O4

> <MOLECULAR_WEIGHT>
268.268

> <EXACT_MASS>
268.073558866

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
27.30684011474326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(8-methyl-9-oxo-9H-xanthen-4-yl)acetic acid

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
3.110809898999999

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4794573994561833

> <JCHEM_PKA_STRONGEST_BASIC>
-3.762239428282149

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
73.16510000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8-methyl-9-oxoxanthen-4-yl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0244424
     RDKit          3D
8-Methylxanthen-9-one-4-acetic acid
 32 34  0  0  0  0  0  0  0  0999 V2000
    4.0910    0.3236    0.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8612    1.1296   -0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9389    2.4925   -0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8226    3.2675   -0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5966    2.6226   -0.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4640    1.2643   -0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7033    0.6570   -0.2991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8262   -0.6320   -0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0692   -1.2172   -0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2588   -0.3649   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6758    0.3670    0.8480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0461    0.2298    1.9152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7710    1.2034    0.7936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2128   -2.5839    0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1233   -3.3994    0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1221   -2.8049    0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2863   -1.4510    0.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5353   -0.8490    0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5239   -1.5763    0.3620 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6223    0.5103   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0931   -0.1252    1.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2564   -0.3543   -0.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9571    1.0499    0.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9084    2.9913   -0.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8951    4.3551   -0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2858    3.2336   -0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1125    0.3500   -1.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0960   -1.0394   -0.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3846    1.2735   -0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1980   -3.0597    0.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2231   -4.4735    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0122   -3.3903    0.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  9 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20  2  1  0
 20  6  2  0
 17  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
M  END

HEADER    PROTEIN                                 10-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-21         0                                  
HETATM    1  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -0.770   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  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    4    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    3   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    9   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0244424
HETATM    1  C1  UNL     1       4.091   0.324   0.234  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.861   1.130  -0.020  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.939   2.493  -0.224  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.823   3.267  -0.455  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.597   2.623  -0.476  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.464   1.264  -0.278  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.703   0.657  -0.299  1.00  0.00           O  
HETATM    8  C7  UNL     1      -0.826  -0.632  -0.113  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.069  -1.217  -0.146  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.259  -0.365  -0.374  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.676   0.367   0.848  1.00  0.00           C  
HETATM   12  O2  UNL     1      -3.046   0.230   1.915  1.00  0.00           O  
HETATM   13  O3  UNL     1      -4.771   1.203   0.794  1.00  0.00           O  
HETATM   14  C11 UNL     1      -2.213  -2.584   0.048  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.123  -3.399   0.280  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.122  -2.805   0.312  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.286  -1.451   0.122  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.535  -0.849   0.153  1.00  0.00           C  
HETATM   19  O4  UNL     1       2.524  -1.576   0.362  1.00  0.00           O  
HETATM   20  C16 UNL     1       1.622   0.510  -0.047  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.093  -0.125   1.248  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.256  -0.354  -0.595  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.957   1.050   0.245  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.908   2.991  -0.205  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.895   4.355  -0.615  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.286   3.234  -0.660  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.113   0.350  -1.210  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.096  -1.039  -0.657  1.00  0.00           H  
HETATM   29  H9  UNL     1      -5.385   1.274  -0.012  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.198  -3.060   0.025  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.223  -4.473   0.434  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.012  -3.390   0.489  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3   20
CONECT    3    4   24
CONECT    4    5    5   25
CONECT    5    6   26
CONECT    6    7   20   20
CONECT    7    8
CONECT    8    9    9   17
CONECT    9   10   14
CONECT   10   11   27   28
CONECT   11   12   12   13
CONECT   13   29
CONECT   14   15   15   30
CONECT   15   16   31
CONECT   16   17   17   32
CONECT   17   18
CONECT   18   19   19   20
END

HMDB0244424
     RDKit          3D
8-Methylxanthen-9-one-4-acetic acid
 32 34  0  0  0  0  0  0  0  0999 V2000
    4.0910    0.3236    0.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8612    1.1296   -0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9389    2.4925   -0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8226    3.2675   -0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5966    2.6226   -0.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4640    1.2643   -0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7033    0.6570   -0.2991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8262   -0.6320   -0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0692   -1.2172   -0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2588   -0.3649   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6758    0.3670    0.8480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0461    0.2298    1.9152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7710    1.2034    0.7936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2128   -2.5839    0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1233   -3.3994    0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1221   -2.8049    0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2863   -1.4510    0.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5353   -0.8490    0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5239   -1.5763    0.3620 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6223    0.5103   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0931   -0.1252    1.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2564   -0.3543   -0.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9571    1.0499    0.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9084    2.9913   -0.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8951    4.3551   -0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2858    3.2336   -0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1125    0.3500   -1.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0960   -1.0394   -0.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3846    1.2735   -0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1980   -3.0597    0.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2231   -4.4735    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0122   -3.3903    0.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  9 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20  2  1  0
 20  6  2  0
 17  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-Methylxanthen-9-one-4-acetic acid	MeSH
8-Methylxanthenone-4-acetic acid	MeSH
8-Methylxanthen-9-one-4-acetate	Generator

Chemical Formula

C₁₆H₁₂O₄

Average Molecular Weight

268.268

Monoisotopic Molecular Weight

268.073558866

IUPAC Name

2-(8-methyl-9-oxo-9H-xanthen-4-yl)acetic acid

Traditional Name

(8-methyl-9-oxoxanthen-4-yl)acetic acid

CAS Registry Number

Not Available

SMILES

CC1=C2C(=O)C3=C(OC2=CC=C1)C(CC(O)=O)=CC=C3

InChI Identifier

InChI=1S/C16H12O4/c1-9-4-2-7-12-14(9)15(19)11-6-3-5-10(8-13(17)18)16(11)20-12/h2-7H,8H2,1H3,(H,17,18)

InChI Key

LOMULPZJAGQWGF-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
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	2.86	ALOGPS
logP	3.11	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.48	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	73.17 m³·mol⁻¹	ChemAxon
Polarizability	27.31 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]+	158.404	30932474
DeepCCS	[M-H]-	156.046	30932474
DeepCCS	[M-2H]-	190.426	30932474
DeepCCS	[M+Na]+	165.467	30932474
AllCCS	[M+H]+	159.7	32859911
AllCCS	[M+H-H2O]+	155.9	32859911
AllCCS	[M+NH4]+	163.3	32859911
AllCCS	[M+Na]+	164.4	32859911
AllCCS	[M-H]-	163.2	32859911
AllCCS	[M+Na-2H]-	162.5	32859911
AllCCS	[M+HCOO]-	161.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Methylxanthen-9-one-4-acetic acid	CC1=C2C(=O)C3=C(OC2=CC=C1)C(CC(O)=O)=CC=C3	3539.5	Standard polar	33892256
8-Methylxanthen-9-one-4-acetic acid	CC1=C2C(=O)C3=C(OC2=CC=C1)C(CC(O)=O)=CC=C3	2341.4	Standard non polar	33892256
8-Methylxanthen-9-one-4-acetic acid	CC1=C2C(=O)C3=C(OC2=CC=C1)C(CC(O)=O)=CC=C3	2534.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Methylxanthen-9-one-4-acetic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xr-2790000000-5548c2088a301213ea33	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Methylxanthen-9-one-4-acetic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Methylxanthen-9-one-4-acetic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Methylxanthen-9-one-4-acetic acid GC-MS (TBDMS_1_1) - 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 - 8-Methylxanthen-9-one-4-acetic acid 10V, Positive-QTOF	splash10-0udi-0090000000-64c7c8666d02d4d1c7bc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Methylxanthen-9-one-4-acetic acid 20V, Positive-QTOF	splash10-0fk9-0090000000-a55489e5cdbebbd23c77	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Methylxanthen-9-one-4-acetic acid 40V, Positive-QTOF	splash10-0abc-3970000000-4378d96a1322952d702c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Methylxanthen-9-one-4-acetic acid 10V, Negative-QTOF	splash10-00di-0090000000-2f2fd855bc791d731cbb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Methylxanthen-9-one-4-acetic acid 20V, Negative-QTOF	splash10-00di-0090000000-2ee08f480428f62baef5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Methylxanthen-9-one-4-acetic acid 40V, Negative-QTOF	splash10-0002-0980000000-3bbc788516014329499d	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

342098

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

386025

PDB ID

Not Available

ChEBI ID

Not Available

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 8-Methylxanthen-9-one-4-acetic acid (HMDB0244424)

MOL for HMDB0244424 (8-Methylxanthen-9-one-4-acetic acid)

3D MOL for HMDB0244424 (8-Methylxanthen-9-one-4-acetic acid)

3D SDF for HMDB0244424 (8-Methylxanthen-9-one-4-acetic acid)

3D-SDF for HMDB0244424 (8-Methylxanthen-9-one-4-acetic acid)

PDB for HMDB0244424 (8-Methylxanthen-9-one-4-acetic acid)

3D PDB for HMDB0244424 (8-Methylxanthen-9-one-4-acetic acid)

SMILES for HMDB0244424 (8-Methylxanthen-9-one-4-acetic acid)

INCHI for HMDB0244424 (8-Methylxanthen-9-one-4-acetic acid)

Structure for HMDB0244424 (8-Methylxanthen-9-one-4-acetic acid)

3D Structure for HMDB0244424 (8-Methylxanthen-9-one-4-acetic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra