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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:37:57 UTC

Update Date

2021-09-26 23:03:14 UTC

HMDB ID

HMDB0251297

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dihydrocitrinone

Description

3,4-dihydro-6,8-dihydroxy-3,4,5-trimethyl-isocoumarin-7-carboxylic acid belongs to the class of organic compounds known as m-phthalate esters. These are ester derivatives of m-phthalic acids, which are based on a benzene 1,3-dicarboxylic acid skeleton. 3,4-dihydro-6,8-dihydroxy-3,4,5-trimethyl-isocoumarin-7-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Dihydrocitrinone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dihydrocitrinone 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

HMDB0251297
     RDKit          3D
Dihydrocitrinone
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.0485   -2.6188   -0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4781   -1.2377   -0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8433   -1.0775    0.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6189   -2.1751    0.4892 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4397    0.1822    0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8693    0.2395    0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4910   -0.8330    0.6517 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6492    1.3768    0.3348 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493    1.2479   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1639    2.5068   -0.3433 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2770    1.0514   -0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246   -0.1857   -0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7566   -0.3469   -0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4941   -1.1731    0.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4922    1.0039   -0.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016    1.4290    0.8415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8192    2.0429   -1.1944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4867    2.2499   -0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0678    3.3788   -0.9646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0726   -3.0650    0.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9894   -2.7587   -0.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6551   -3.3225   -0.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2305   -3.0807    0.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1791    1.5827   -0.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0955    2.7509   -0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0011   -0.7729   -1.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1305   -1.9811   -0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2843   -0.5736    0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8660   -1.5434    1.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4824    0.8489   -1.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6212    2.5417    0.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411    0.9684    1.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8954    1.3444    1.0757 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 12  2  1  0
 18 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  8 24  1  0
 10 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
M  END

  Mrv1533004161514392D          

 19 20  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   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   -1.6500    0.0000 O   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
    2.8579   -2.4750    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
    1.4289   -1.6500    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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  9 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251297

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1OC(=O)C2=C(O)C(C(O)=O)=C(O)C(C)=C2C1C

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O6/c1-4-6(3)19-13(18)8-7(4)5(2)10(14)9(11(8)15)12(16)17/h4,6,14-15H,1-3H3,(H,16,17)

> <INCHI_KEY>
VVVMDYGNIVXIIG-UHFFFAOYSA-N

> <FORMULA>
C13H14O6

> <MOLECULAR_WEIGHT>
266.249

> <EXACT_MASS>
266.079038171

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.932145409505058

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,8-dihydroxy-3,4,5-trimethyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid

> <ALOGPS_LOGP>
2.33

> <JCHEM_LOGP>
4.112032791333333

> <ALOGPS_LOGS>
-2.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.032691771437618

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2763371422065646

> <JCHEM_PKA_STRONGEST_BASIC>
-4.288314791773382

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
66.5425

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,8-dihydroxy-3,4,5-trimethyl-1-oxo-3,4-dihydro-2-benzopyran-7-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251297
     RDKit          3D
Dihydrocitrinone
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.0485   -2.6188   -0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4781   -1.2377   -0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8433   -1.0775    0.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6189   -2.1751    0.4892 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4397    0.1822    0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8693    0.2395    0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4910   -0.8330    0.6517 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6492    1.3768    0.3348 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493    1.2479   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1639    2.5068   -0.3433 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2770    1.0514   -0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246   -0.1857   -0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7566   -0.3469   -0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4941   -1.1731    0.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4922    1.0039   -0.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016    1.4290    0.8415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8192    2.0429   -1.1944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4867    2.2499   -0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0678    3.3788   -0.9646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0726   -3.0650    0.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9894   -2.7587   -0.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6551   -3.3225   -0.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2305   -3.0807    0.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1791    1.5827   -0.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0955    2.7509   -0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0011   -0.7729   -1.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1305   -1.9811   -0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2843   -0.5736    0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8660   -1.5434    1.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4824    0.8489   -1.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6212    2.5417    0.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411    0.9684    1.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8954    1.3444    1.0757 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 12  2  1  0
 18 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  8 24  1  0
 10 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 16 33  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  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+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       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   17                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    6   18                                                  
CONECT   18   17    2   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0251297
HETATM    1  C1  UNL     1      -0.048  -2.619  -0.029  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.478  -1.238  -0.089  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.843  -1.078   0.159  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.619  -2.175   0.489  1.00  0.00           O  
HETATM    5  C4  UNL     1       2.440   0.182   0.080  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.869   0.239   0.358  1.00  0.00           C  
HETATM    7  O2  UNL     1       4.491  -0.833   0.652  1.00  0.00           O  
HETATM    8  O3  UNL     1       4.649   1.377   0.335  1.00  0.00           O  
HETATM    9  C6  UNL     1       1.649   1.248  -0.247  1.00  0.00           C  
HETATM   10  O4  UNL     1       2.164   2.507  -0.343  1.00  0.00           O  
HETATM   11  C7  UNL     1       0.277   1.051  -0.491  1.00  0.00           C  
HETATM   12  C8  UNL     1      -0.325  -0.186  -0.414  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.757  -0.347  -0.622  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.494  -1.173   0.396  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.492   1.004  -0.588  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.802   1.429   0.841  1.00  0.00           C  
HETATM   17  O5  UNL     1      -1.819   2.043  -1.194  1.00  0.00           O  
HETATM   18  C13 UNL     1      -0.487   2.250  -0.899  1.00  0.00           C  
HETATM   19  O6  UNL     1       0.068   3.379  -0.965  1.00  0.00           O  
HETATM   20  H1  UNL     1      -0.073  -3.065   0.962  1.00  0.00           H  
HETATM   21  H2  UNL     1      -0.989  -2.759  -0.635  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.655  -3.323  -0.599  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.230  -3.081   0.566  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.179   1.583  -0.518  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.095   2.751  -0.195  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.001  -0.773  -1.626  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.131  -1.981  -0.071  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.284  -0.574   0.944  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.866  -1.543   1.229  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.482   0.849  -1.085  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.621   2.542   0.942  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.141   0.968   1.581  1.00  0.00           H  
HETATM   33  H14 UNL     1      -3.895   1.344   1.076  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3   12
CONECT    3    4    5
CONECT    4   23
CONECT    5    6    9    9
CONECT    6    7    7    8
CONECT    8   24
CONECT    9   10   11
CONECT   10   25
CONECT   11   12   12   18
CONECT   12   13
CONECT   13   14   15   26
CONECT   14   27   28   29
CONECT   15   16   17   30
CONECT   16   31   32   33
CONECT   17   18
CONECT   18   19   19
END

HMDB0251297
     RDKit          3D
Dihydrocitrinone
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.0485   -2.6188   -0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4781   -1.2377   -0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8433   -1.0775    0.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6189   -2.1751    0.4892 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4397    0.1822    0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8693    0.2395    0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4910   -0.8330    0.6517 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6492    1.3768    0.3348 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493    1.2479   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1639    2.5068   -0.3433 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2770    1.0514   -0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246   -0.1857   -0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7566   -0.3469   -0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4941   -1.1731    0.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4922    1.0039   -0.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016    1.4290    0.8415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8192    2.0429   -1.1944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4867    2.2499   -0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0678    3.3788   -0.9646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0726   -3.0650    0.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9894   -2.7587   -0.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6551   -3.3225   -0.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2305   -3.0807    0.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1791    1.5827   -0.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0955    2.7509   -0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0011   -0.7729   -1.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1305   -1.9811   -0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2843   -0.5736    0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8660   -1.5434    1.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4824    0.8489   -1.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6212    2.5417    0.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411    0.9684    1.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8954    1.3444    1.0757 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 12  2  1  0
 18 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  8 24  1  0
 10 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4-Dihydro-6,8-dihydroxy-3,4,5-trimethyl-isocoumarin-7-carboxylate	Generator
Dihydrocitrinone	MeSH

Chemical Formula

C₁₃H₁₄O₆

Average Molecular Weight

266.249

Monoisotopic Molecular Weight

266.079038171

IUPAC Name

6,8-dihydroxy-3,4,5-trimethyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid

Traditional Name

6,8-dihydroxy-3,4,5-trimethyl-1-oxo-3,4-dihydro-2-benzopyran-7-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1OC(=O)C2=C(O)C(C(O)=O)=C(O)C(C)=C2C1C

InChI Identifier

InChI=1S/C13H14O6/c1-4-6(3)19-13(18)8-7(4)5(2)10(14)9(11(8)15)12(16)17/h4,6,14-15H,1-3H3,(H,16,17)

InChI Key

VVVMDYGNIVXIIG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-phthalate esters. These are ester derivatives of m-phthalic acids, which are based on a benzene 1,3-dicarboxylic acid skeleton.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

m-Phthalate esters

Alternative Parents

Substituents

Meta-phthalic acid ester
Meta_phthalic_acid
Dihydroxybenzoic acid
Benzopyran
Isochromane
Hydroxybenzoic acid
2-benzopyran
Salicylic acid or derivatives
Phenol
Vinylogous acid
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen 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)

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	2.33	ALOGPS
logP	4.11	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.28	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	66.54 m³·mol⁻¹	ChemAxon
Polarizability	25.93 Å³	ChemAxon
Number of Rings	2	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]+	157.848	30932474
DeepCCS	[M-H]-	155.49	30932474
DeepCCS	[M-2H]-	189.092	30932474
DeepCCS	[M+Na]+	164.236	30932474
AllCCS	[M+H]+	158.4	32859911
AllCCS	[M+H-H2O]+	154.9	32859911
AllCCS	[M+NH4]+	161.5	32859911
AllCCS	[M+Na]+	162.4	32859911
AllCCS	[M-H]-	160.1	32859911
AllCCS	[M+Na-2H]-	160.0	32859911
AllCCS	[M+HCOO]-	160.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydrocitrinone	CC1OC(=O)C2=C(O)C(C(O)=O)=C(O)C(C)=C2C1C	3406.1	Standard polar	33892256
Dihydrocitrinone	CC1OC(=O)C2=C(O)C(C(O)=O)=C(O)C(C)=C2C1C	2144.7	Standard non polar	33892256
Dihydrocitrinone	CC1OC(=O)C2=C(O)C(C(O)=O)=C(O)C(C)=C2C1C	2335.2	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 - Dihydrocitrinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ds-0290000000-6743eee223e51d0b6b66	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocitrinone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocitrinone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocitrinone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocitrinone GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocitrinone GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocitrinone GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocitrinone GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocitrinone GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocitrinone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocitrinone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocitrinone GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocitrinone GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocitrinone GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocitrinone GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrocitrinone GC-MS (TBDMS_3_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 - Dihydrocitrinone 10V, Positive-QTOF	splash10-014j-0090000000-9648168fc9255e7a6bc1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocitrinone 20V, Positive-QTOF	splash10-0002-0090000000-57495219811e551cca25	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocitrinone 40V, Positive-QTOF	splash10-0fi0-1920000000-4139e44ed389034df190	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocitrinone 10V, Negative-QTOF	splash10-014i-0090000000-45acf07b07fc3e1cd640	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocitrinone 20V, Negative-QTOF	splash10-00xs-0290000000-8cb60d1333a19c35c301	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocitrinone 40V, Negative-QTOF	splash10-05i1-4950000000-3c0d3731a0af2805480a	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15558919

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 Dihydrocitrinone (HMDB0251297)

MOL for HMDB0251297 (Dihydrocitrinone)

3D MOL for HMDB0251297 (Dihydrocitrinone)

3D SDF for HMDB0251297 (Dihydrocitrinone)

3D-SDF for HMDB0251297 (Dihydrocitrinone)

PDB for HMDB0251297 (Dihydrocitrinone)

3D PDB for HMDB0251297 (Dihydrocitrinone)

SMILES for HMDB0251297 (Dihydrocitrinone)

INCHI for HMDB0251297 (Dihydrocitrinone)

Structure for HMDB0251297 (Dihydrocitrinone)

3D Structure for HMDB0251297 (Dihydrocitrinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra