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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 16:32:06 UTC

Update Date

2021-09-23 16:32:06 UTC

HMDB ID

HMDB0302278

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Xanthoxotin

Description

Xanthoxotin is a member of the class of compounds known as acridones. Acridones are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety. Xanthoxotin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Xanthoxotin can be found in wild celery, which makes xanthoxotin a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302278
     RDKit          3D
Xanthoxotin
 33 35  0  0  0  0  0  0  0  0999 V2000
    3.2958    2.8343    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2839    1.5113   -0.1959 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068    0.8161   -0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9526    1.3869    0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2194    0.6679    0.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3642    1.2413    0.6013 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5209    0.5469    0.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6948    1.1178    1.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8696    0.3914    0.9632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9373   -0.9024    0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7431   -1.4650    0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5729   -0.7494    0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3923   -1.3047   -0.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3588   -2.4979   -0.7844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1976   -0.6257   -0.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9913   -1.1929   -0.7548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9134   -2.5011   -1.2242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1729   -0.4841   -0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3174   -1.0835   -1.1632 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2073   -1.8296   -0.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3083    3.2619    0.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5041    3.4140   -0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1053    2.8762    1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9179    2.4155    0.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3364    2.2165    0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6636    2.1348    1.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7996    0.8569    1.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8736   -1.4216    0.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7717   -2.4866   -0.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7768   -2.9210   -1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9885   -2.2332   -1.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7305   -1.2712    0.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7431   -2.7198    0.0816 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  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 18  3  1  0
 15  5  2  0
 12  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 17 30  1  0
 20 31  1  0
 20 32  1  0
 20 33  1  0
M  END

  Mrv1533004171519552D          

 20 22  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
    2.1434   -1.2375    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
    3.5724   -1.2375    0.0000 N   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
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   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
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   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
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  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
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  5 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
  3 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302278

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C(O)=C1OC)C(=O)C1=CC=CC=C1N2

> <INCHI_IDENTIFIER>
InChI=1S/C15H13NO4/c1-19-11-7-10-12(14(18)15(11)20-2)13(17)8-5-3-4-6-9(8)16-10/h3-7,18H,1-2H3,(H,16,17)

> <INCHI_KEY>
CYPILPIHKOUTNO-UHFFFAOYSA-N

> <FORMULA>
C15H13NO4

> <MOLECULAR_WEIGHT>
271.272

> <EXACT_MASS>
271.084457903

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.80754043261871

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-hydroxy-2,3-dimethoxy-9,10-dihydroacridin-9-one

> <ALOGPS_LOGP>
3.25

> <JCHEM_LOGP>
4.230370959666667

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.444001676606977

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.42404634832809

> <JCHEM_PKA_STRONGEST_BASIC>
-2.026908602907003

> <JCHEM_POLAR_SURFACE_AREA>
67.79

> <JCHEM_REFRACTIVITY>
73.96900000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-2,3-dimethoxy-10H-acridin-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302278
     RDKit          3D
Xanthoxotin
 33 35  0  0  0  0  0  0  0  0999 V2000
    3.2958    2.8343    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2839    1.5113   -0.1959 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068    0.8161   -0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9526    1.3869    0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2194    0.6679    0.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3642    1.2413    0.6013 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5209    0.5469    0.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6948    1.1178    1.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8696    0.3914    0.9632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9373   -0.9024    0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7431   -1.4650    0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5729   -0.7494    0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3923   -1.3047   -0.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3588   -2.4979   -0.7844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1976   -0.6257   -0.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9913   -1.1929   -0.7548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9134   -2.5011   -1.2242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1729   -0.4841   -0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3174   -1.0835   -1.1632 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2073   -1.8296   -0.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3083    3.2619    0.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5041    3.4140   -0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1053    2.8762    1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9179    2.4155    0.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3364    2.2165    0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6636    2.1348    1.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7996    0.8569    1.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8736   -1.4216    0.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7717   -2.4866   -0.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7768   -2.9210   -1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9885   -2.2332   -1.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7305   -1.2712    0.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7431   -2.7198    0.0816 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  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 18  3  1  0
 15  5  2  0
 12  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 17 30  1  0
 20 31  1  0
 20 32  1  0
 20 33  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    5   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    3   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0302278
HETATM    1  C1  UNL     1       3.296   2.834   0.292  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.284   1.511  -0.196  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.107   0.816  -0.226  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.953   1.387   0.208  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.219   0.668   0.168  1.00  0.00           C  
HETATM    6  N1  UNL     1      -1.364   1.241   0.601  1.00  0.00           N  
HETATM    7  C5  UNL     1      -2.521   0.547   0.567  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.695   1.118   1.005  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.870   0.391   0.963  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.937  -0.902   0.497  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.743  -1.465   0.058  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.573  -0.749   0.097  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.392  -1.305  -0.336  1.00  0.00           C  
HETATM   14  O2  UNL     1      -1.359  -2.498  -0.784  1.00  0.00           O  
HETATM   15  C12 UNL     1      -0.198  -0.626  -0.315  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.991  -1.193  -0.755  1.00  0.00           C  
HETATM   17  O3  UNL     1       0.913  -2.501  -1.224  1.00  0.00           O  
HETATM   18  C14 UNL     1       2.173  -0.484  -0.720  1.00  0.00           C  
HETATM   19  O4  UNL     1       3.317  -1.084  -1.163  1.00  0.00           O  
HETATM   20  C15 UNL     1       4.207  -1.830  -0.390  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.308   3.262   0.064  1.00  0.00           H  
HETATM   22  H2  UNL     1       2.504   3.414  -0.212  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.105   2.876   1.381  1.00  0.00           H  
HETATM   24  H4  UNL     1       0.918   2.416   0.596  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.336   2.217   0.957  1.00  0.00           H  
HETATM   26  H6  UNL     1      -3.664   2.135   1.376  1.00  0.00           H  
HETATM   27  H7  UNL     1      -5.800   0.857   1.315  1.00  0.00           H  
HETATM   28  H8  UNL     1      -5.874  -1.422   0.486  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.772  -2.487  -0.314  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.777  -2.921  -1.546  1.00  0.00           H  
HETATM   31  H11 UNL     1       4.989  -2.233  -1.090  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.730  -1.271   0.387  1.00  0.00           H  
HETATM   33  H13 UNL     1       3.743  -2.720   0.082  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   18
CONECT    4    5   24
CONECT    5    6   15   15
CONECT    6    7   25
CONECT    7    8    8   12
CONECT    8    9   26
CONECT    9   10   10   27
CONECT   10   11   28
CONECT   11   12   12   29
CONECT   12   13
CONECT   13   14   14   15
CONECT   15   16
CONECT   16   17   18   18
CONECT   17   30
CONECT   18   19
CONECT   19   20
CONECT   20   31   32   33
END

HMDB0302278
     RDKit          3D
Xanthoxotin
 33 35  0  0  0  0  0  0  0  0999 V2000
    3.2958    2.8343    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2839    1.5113   -0.1959 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1068    0.8161   -0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9526    1.3869    0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2194    0.6679    0.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3642    1.2413    0.6013 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5209    0.5469    0.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6948    1.1178    1.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8696    0.3914    0.9632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9373   -0.9024    0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7431   -1.4650    0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5729   -0.7494    0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3923   -1.3047   -0.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3588   -2.4979   -0.7844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1976   -0.6257   -0.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9913   -1.1929   -0.7548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9134   -2.5011   -1.2242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1729   -0.4841   -0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3174   -1.0835   -1.1632 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2073   -1.8296   -0.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3083    3.2619    0.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5041    3.4140   -0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1053    2.8762    1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9179    2.4155    0.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3364    2.2165    0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6636    2.1348    1.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7996    0.8569    1.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8736   -1.4216    0.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7717   -2.4866   -0.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7768   -2.9210   -1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9885   -2.2332   -1.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7305   -1.2712    0.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7431   -2.7198    0.0816 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  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 18  3  1  0
 15  5  2  0
 12  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 17 30  1  0
 20 31  1  0
 20 32  1  0
 20 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₃NO₄

Average Molecular Weight

271.272

Monoisotopic Molecular Weight

271.084457903

IUPAC Name

1-hydroxy-2,3-dimethoxy-9,10-dihydroacridin-9-one

Traditional Name

1-hydroxy-2,3-dimethoxy-10H-acridin-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(O)=C1OC)C(=O)C1=CC=CC=C1N2

InChI Identifier

InChI=1S/C15H13NO4/c1-19-11-7-10-12(14(18)15(11)20-2)13(17)8-5-3-4-6-9(8)16-10/h3-7,18H,1-2H3,(H,16,17)

InChI Key

CYPILPIHKOUTNO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridones

Alternative Parents

Substituents

Acridone
Dihydroquinolone
Dihydroquinoline
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyridine
Benzenoid
Vinylogous amide
Vinylogous acid
Heteroaromatic compound
Ether
Azacycle
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302278)

Food

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

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	3.25	ALOGPS
logP	4.23	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.42	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.79 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	73.97 m³·mol⁻¹	ChemAxon
Polarizability	27.81 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
AllCCS	[M+H]+	160.665	32859911
AllCCS	[M+H-H2O]+	156.828	32859911
AllCCS	[M+Na]+	165.257	32859911
AllCCS	[M+NH4]+	164.231	32859911
AllCCS	[M-H]-	164.417	32859911
AllCCS	[M+Na-2H]-	163.796	32859911
AllCCS	[M+HCOO]-	163.238	32859911
DeepCCS	[M+H]+	158.114	30932474
DeepCCS	[M-H]-	155.756	30932474
DeepCCS	[M-2H]-	189.103	30932474
DeepCCS	[M+Na]+	164.294	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Xanthoxotin,2TMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C)=C1OC)C(=O)C1=CC=CC=C1N2[Si](C)(C)C	2801.5	Semi standard non polar	33892256
Xanthoxotin,2TMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C)=C1OC)C(=O)C1=CC=CC=C1N2[Si](C)(C)C	2665.8	Standard non polar	33892256
Xanthoxotin,2TMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C)=C1OC)C(=O)C1=CC=CC=C1N2[Si](C)(C)C	2896.7	Standard polar	33892256
Xanthoxotin,2TBDMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1OC)C(=O)C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C	3124.5	Semi standard non polar	33892256
Xanthoxotin,2TBDMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1OC)C(=O)C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C	3042.4	Standard non polar	33892256
Xanthoxotin,2TBDMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1OC)C(=O)C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C	3123.6	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxotin 10V, Positive-QTOF	splash10-00di-0090000000-42808506f2e905942154	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxotin 20V, Positive-QTOF	splash10-00di-0090000000-205c21bb237e2bba011c	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxotin 40V, Positive-QTOF	splash10-0ff0-1690000000-030e4ae3a26a7db1cb42	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxotin 10V, Negative-QTOF	splash10-00di-0090000000-f53d5c39dab1510cac8e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxotin 20V, Negative-QTOF	splash10-00di-0090000000-f062449c9eee38d45888	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxotin 40V, Negative-QTOF	splash10-00ls-0910000000-6da75cc5384f22537d10	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxotin 10V, Positive-QTOF	splash10-00di-0090000000-d75dd06255504b226484	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxotin 20V, Positive-QTOF	splash10-00di-0090000000-d75dd06255504b226484	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxotin 40V, Positive-QTOF	splash10-0a71-0690000000-93521857b1d5db48dde2	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxotin 10V, Negative-QTOF	splash10-00di-0090000000-2e11bb63e0942d2d8a1c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxotin 20V, Negative-QTOF	splash10-00di-0190000000-5ef4c0afd8434724c762	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthoxotin 40V, Negative-QTOF	splash10-01b9-1950000000-5d39502817bc5b36e1c3	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB004005

KNApSAcK ID

C00024273

Chemspider ID

4525824

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5376586

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

Not Available

Showing metabocard for Xanthoxotin (HMDB0302278)

MOL for HMDB0302278 (Xanthoxotin)

3D MOL for HMDB0302278 (Xanthoxotin)

3D SDF for HMDB0302278 (Xanthoxotin)

3D-SDF for HMDB0302278 (Xanthoxotin)

PDB for HMDB0302278 (Xanthoxotin)

3D PDB for HMDB0302278 (Xanthoxotin)

SMILES for HMDB0302278 (Xanthoxotin)

INCHI for HMDB0302278 (Xanthoxotin)

Structure for HMDB0302278 (Xanthoxotin)

3D Structure for HMDB0302278 (Xanthoxotin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra