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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:29:22 UTC

Update Date

2021-09-26 23:12:51 UTC

HMDB ID

HMDB0256871

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Protoapigenone

Description

5,7-dihydroxy-2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)-4H-chromen-4-one belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety. Based on a literature review very few articles have been published on 5,7-dihydroxy-2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)-4H-chromen-4-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). Protoapigenone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Protoapigenone 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

HMDB0256871
     RDKit          3D
Protoapigenone
 31 33  0  0  0  0  0  0  0  0999 V2000
   -5.5952    0.1944   -1.6692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5291    0.0958   -1.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7163    1.2538   -0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6090    1.1369    0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1025   -0.1382    0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1741   -0.0676    1.9499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6599   -0.3233    0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1679   -1.4831   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2090   -1.6460   -0.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -2.7365   -0.9743 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0294   -0.5808   -0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3947   -0.6530   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9725   -1.7634   -0.9346 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1620    0.4783   -0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6192    1.6231    0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4043    2.7486    0.6988 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2617    1.6509    0.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4615    0.5610    0.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1690    0.6400    0.4919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9093   -1.2867    0.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0183   -1.1844   -0.5266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0647    2.2477   -0.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0767    2.0832    0.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8031    0.8264    2.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8223   -2.2927   -0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7048   -2.6203   -1.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2351    0.4078   -0.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3965    2.6764    0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8240    2.5507    0.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6146   -2.3219    0.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5936   -2.0771   -0.7652 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  1  0
  5  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
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  5 20  1  0
 20 21  2  0
 21  2  1  0
 19  7  1  0
 18 11  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  8 25  1  0
 13 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 20 30  1  0
 21 31  1  0
M  END

  Mrv1533004161522162D          

 21 23  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 O   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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7565   -2.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690   -0.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3815   -0.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9118   -1.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7242   -1.2202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6296   -2.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8171   -2.2820    0.0000 C   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  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
  2 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  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
 20 21  2  0  0  0  0
 14 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256871

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1(O)C=CC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O6/c16-8-1-3-15(20,4-2-8)13-7-11(19)14-10(18)5-9(17)6-12(14)21-13/h1-7,17-18,20H

> <INCHI_KEY>
DLMOVPAUHQQYHA-UHFFFAOYSA-N

> <FORMULA>
C15H10O6

> <MOLECULAR_WEIGHT>
286.239

> <EXACT_MASS>
286.047738042

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.849474815265413

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)-4H-chromen-4-one

> <ALOGPS_LOGP>
1.65

> <JCHEM_LOGP>
1.7187960786666667

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.181783265830717

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.5790174523054645

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8343011494955617

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
76.03649999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256871
     RDKit          3D
Protoapigenone
 31 33  0  0  0  0  0  0  0  0999 V2000
   -5.5952    0.1944   -1.6692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5291    0.0958   -1.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7163    1.2538   -0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6090    1.1369    0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1025   -0.1382    0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1741   -0.0676    1.9499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6599   -0.3233    0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1679   -1.4831   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2090   -1.6460   -0.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -2.7365   -0.9743 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0294   -0.5808   -0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3947   -0.6530   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9725   -1.7634   -0.9346 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1620    0.4783   -0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6192    1.6231    0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4043    2.7486    0.6988 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2617    1.6509    0.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4615    0.5610    0.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1690    0.6400    0.4919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9093   -1.2867    0.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0183   -1.1844   -0.5266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0647    2.2477   -0.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0767    2.0832    0.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8031    0.8264    2.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8223   -2.2927   -0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7048   -2.6203   -1.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2351    0.4078   -0.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3965    2.6764    0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8240    2.5507    0.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6146   -2.3219    0.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5936   -2.0771   -0.7652 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  1  0
  5  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
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  5 20  1  0
 20 21  2  0
 21  2  1  0
 19  7  1  0
 18 11  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  8 25  1  0
 13 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 20 30  1  0
 21 31  1  0
M  END

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.012  -4.260   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.529  -1.633   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.045  -1.365   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.035  -2.545   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.552  -2.278   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.509  -3.992   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.992  -4.260   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12    2                                                       
CONECT   14   10   15   16   21                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0256871
HETATM    1  O1  UNL     1      -5.595   0.194  -1.669  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.529   0.096  -1.003  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.716   1.254  -0.653  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.609   1.137   0.041  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.102  -0.138   0.513  1.00  0.00           C  
HETATM    6  O2  UNL     1      -2.174  -0.068   1.950  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.660  -0.323   0.245  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.168  -1.483  -0.258  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.209  -1.646  -0.509  1.00  0.00           C  
HETATM   10  O3  UNL     1       1.613  -2.736  -0.974  1.00  0.00           O  
HETATM   11  C8  UNL     1       2.029  -0.581  -0.223  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.395  -0.653  -0.438  1.00  0.00           C  
HETATM   13  O4  UNL     1       3.972  -1.763  -0.935  1.00  0.00           O  
HETATM   14  C10 UNL     1       4.162   0.478  -0.120  1.00  0.00           C  
HETATM   15  C11 UNL     1       3.619   1.623   0.385  1.00  0.00           C  
HETATM   16  O5  UNL     1       4.404   2.749   0.699  1.00  0.00           O  
HETATM   17  C12 UNL     1       2.262   1.651   0.582  1.00  0.00           C  
HETATM   18  C13 UNL     1       1.461   0.561   0.284  1.00  0.00           C  
HETATM   19  O6  UNL     1       0.169   0.640   0.492  1.00  0.00           O  
HETATM   20  C14 UNL     1      -2.909  -1.287   0.166  1.00  0.00           C  
HETATM   21  C15 UNL     1      -4.018  -1.184  -0.527  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.065   2.248  -0.993  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.077   2.083   0.246  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.803   0.826   2.213  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.822  -2.293  -0.472  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.705  -2.620  -1.219  1.00  0.00           H  
HETATM   27  H6  UNL     1       5.235   0.408  -0.294  1.00  0.00           H  
HETATM   28  H7  UNL     1       5.396   2.676   0.535  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.824   2.551   0.980  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.615  -2.322   0.481  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.594  -2.077  -0.765  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4    4   22
CONECT    4    5   23
CONECT    5    6    7   20
CONECT    6   24
CONECT    7    8    8   19
CONECT    8    9   25
CONECT    9   10   10   11
CONECT   11   12   12   18
CONECT   12   13   14
CONECT   13   26
CONECT   14   15   15   27
CONECT   15   16   17
CONECT   16   28
CONECT   17   18   18   29
CONECT   18   19
CONECT   20   21   21   30
CONECT   21   31
END

HMDB0256871
     RDKit          3D
Protoapigenone
 31 33  0  0  0  0  0  0  0  0999 V2000
   -5.5952    0.1944   -1.6692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5291    0.0958   -1.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7163    1.2538   -0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6090    1.1369    0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1025   -0.1382    0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1741   -0.0676    1.9499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6599   -0.3233    0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1679   -1.4831   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2090   -1.6460   -0.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -2.7365   -0.9743 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0294   -0.5808   -0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3947   -0.6530   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9725   -1.7634   -0.9346 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1620    0.4783   -0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6192    1.6231    0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4043    2.7486    0.6988 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2617    1.6509    0.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4615    0.5610    0.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1690    0.6400    0.4919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9093   -1.2867    0.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0183   -1.1844   -0.5266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0647    2.2477   -0.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0767    2.0832    0.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8031    0.8264    2.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8223   -2.2927   -0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7048   -2.6203   -1.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2351    0.4078   -0.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3965    2.6764    0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8240    2.5507    0.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6146   -2.3219    0.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5936   -2.0771   -0.7652 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  1  0
  5  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
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  5 20  1  0
 20 21  2  0
 21  2  1  0
 19  7  1  0
 18 11  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  8 25  1  0
 13 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 20 30  1  0
 21 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
WYC02	MeSH

Chemical Formula

C₁₅H₁₀O₆

Average Molecular Weight

286.239

Monoisotopic Molecular Weight

286.047738042

IUPAC Name

5,7-dihydroxy-2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)-4H-chromen-4-one

Traditional Name

5,7-dihydroxy-2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)chromen-4-one

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1(O)C=CC(=O)C=C1

InChI Identifier

InChI=1S/C15H10O6/c16-8-1-3-15(20,4-2-8)13-7-11(19)14-10(18)5-9(17)6-12(14)21-13/h1-7,17-18,20H

InChI Key

DLMOVPAUHQQYHA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Chromones

Alternative Parents

Substituents

Chromone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Tertiary alcohol
Ketone
Cyclic ketone
Oxacycle
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
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)

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	1.65	ALOGPS
logP	1.72	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.58	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.04 m³·mol⁻¹	ChemAxon
Polarizability	26.85 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]+	166.81	30932474
DeepCCS	[M-H]-	164.452	30932474
DeepCCS	[M-2H]-	198.065	30932474
DeepCCS	[M+Na]+	173.292	30932474
AllCCS	[M+H]+	163.8	32859911
AllCCS	[M+H-H2O]+	160.2	32859911
AllCCS	[M+NH4]+	167.1	32859911
AllCCS	[M+Na]+	168.1	32859911
AllCCS	[M-H]-	164.2	32859911
AllCCS	[M+Na-2H]-	163.5	32859911
AllCCS	[M+HCOO]-	162.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Protoapigenone	OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1(O)C=CC(=O)C=C1	4328.5	Standard polar	33892256
Protoapigenone	OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1(O)C=CC(=O)C=C1	2507.5	Standard non polar	33892256
Protoapigenone	OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1(O)C=CC(=O)C=C1	2995.6	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 - Protoapigenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-3490000000-942c766175edf03569de	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoapigenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoapigenone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoapigenone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoapigenone GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoapigenone GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoapigenone GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoapigenone GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoapigenone GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoapigenone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoapigenone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoapigenone GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoapigenone GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoapigenone GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoapigenone GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoapigenone GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	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

9819646

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11644907

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 Protoapigenone (HMDB0256871)

MOL for HMDB0256871 (Protoapigenone)

3D MOL for HMDB0256871 (Protoapigenone)

3D SDF for HMDB0256871 (Protoapigenone)

3D-SDF for HMDB0256871 (Protoapigenone)

PDB for HMDB0256871 (Protoapigenone)

3D PDB for HMDB0256871 (Protoapigenone)

SMILES for HMDB0256871 (Protoapigenone)

INCHI for HMDB0256871 (Protoapigenone)

Structure for HMDB0256871 (Protoapigenone)

3D Structure for HMDB0256871 (Protoapigenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra