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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 19:07:42 UTC

Update Date

2021-09-26 23:14:37 UTC

HMDB ID

HMDB0257970

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione

Description

1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Based on a literature review very few articles have been published on 1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1-[(2r,4s,5s)-5-[difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione 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

HMDB0257970
     RDKit          3D
1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4...
 28 29  0  0  0  0  0  0  0  0999 V2000
    5.4229    0.4297    0.1187 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1578    0.3262    0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3783    0.8519   -0.8956 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042    0.7130   -0.8579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3778    0.0708    0.1443 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0431   -0.0869    0.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417   -1.3046   -0.5332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0133   -0.9625   -0.6575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6378   -1.3633    0.5140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9800    0.5269   -0.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8580    1.1989    0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1873    0.8786    0.1982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6564    2.5749    0.1515 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4298    0.9002    1.5861 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6759    0.9429   -0.4859 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1554   -0.4341    1.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926   -1.0459    2.0755 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5087   -0.3111    1.1023 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8370    1.3682   -1.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3823    1.1307   -1.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4240   -0.1651    1.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3664   -2.2478    0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1075   -1.3468   -1.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4568   -1.4380   -1.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6703   -2.3671    0.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2359    0.8408   -1.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6355    1.0350    1.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1026   -0.7156    1.8765 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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 10 15  1  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
 18  2  1  0
 15  6  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 18 28  1  0
M  END


  Mrv1652309112121082D          

 18 19  0  0  0  0            999 V2000
    1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    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 N   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6679   -3.8419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8504   -2.6896    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.4845   -3.6594    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -3.1745    0.0000 O   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  1  0  0  0  0
  1  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
  9 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
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257970

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1CC(OC1C(O)(F)F)N1C=CC(=O)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10F2N2O5/c10-9(11,17)7-4(14)3-6(18-7)13-2-1-5(15)12-8(13)16/h1-2,4,6-7,14,17H,3H2,(H,12,15,16)

> <INCHI_KEY>
DGVFFRFCTNNUCI-UHFFFAOYSA-N

> <FORMULA>
C9H10F2N2O5

> <MOLECULAR_WEIGHT>
264.185

> <EXACT_MASS>
264.055777756

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.24942998551974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-{5-[difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl}-1,2,3,4-tetrahydropyrimidine-2,4-dione

> <ALOGPS_LOGP>
-0.67

> <JCHEM_LOGP>
-0.6664653813333332

> <ALOGPS_LOGS>
-0.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.905786572518892

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.14670336884799

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3313530387780643

> <JCHEM_POLAR_SURFACE_AREA>
99.10000000000001

> <JCHEM_REFRACTIVITY>
51.61999999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.59e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-{5-[difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl}-3H-pyrimidine-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0257970
     RDKit          3D
1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4...
 28 29  0  0  0  0  0  0  0  0999 V2000
    5.4229    0.4297    0.1187 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1578    0.3262    0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3783    0.8519   -0.8956 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042    0.7130   -0.8579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3778    0.0708    0.1443 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0431   -0.0869    0.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417   -1.3046   -0.5332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0133   -0.9625   -0.6575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6378   -1.3633    0.5140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9800    0.5269   -0.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8580    1.1989    0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1873    0.8786    0.1982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6564    2.5749    0.1515 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4298    0.9002    1.5861 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6759    0.9429   -0.4859 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1554   -0.4341    1.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926   -1.0459    2.0755 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5087   -0.3111    1.1023 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8370    1.3682   -1.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3823    1.1307   -1.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4240   -0.1651    1.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3664   -2.2478    0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1075   -1.3468   -1.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4568   -1.4380   -1.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6703   -2.3671    0.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2359    0.8408   -1.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6355    1.0350    1.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1026   -0.7156    1.8765 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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 10 15  1  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
 18  2  1  0
 15  6  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 18 28  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.088  -3.215   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.342  -5.926   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.247  -7.172   0.000  0.00  0.00           O+0
HETATM   16  F   UNK     0      -1.587  -5.021   0.000  0.00  0.00           F+0
HETATM   17  F   UNK     0       0.904  -6.831   0.000  0.00  0.00           F+0
HETATM   18  O   UNK     0       3.009  -5.926   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12                                                            
CONECT   14    3   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18    2                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0257970
HETATM    1  O1  UNL     1       5.423   0.430   0.119  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.158   0.326   0.112  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.378   0.852  -0.896  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.004   0.713  -0.858  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.378   0.071   0.144  1.00  0.00           N  
HETATM    6  C4  UNL     1      -0.043  -0.087   0.207  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.542  -1.305  -0.533  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.013  -0.963  -0.657  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.638  -1.363   0.514  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.980   0.527  -0.721  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.858   1.199   0.308  1.00  0.00           C  
HETATM   12  O3  UNL     1      -4.187   0.879   0.198  1.00  0.00           O  
HETATM   13  F1  UNL     1      -2.656   2.575   0.152  1.00  0.00           F  
HETATM   14  F2  UNL     1      -2.430   0.900   1.586  1.00  0.00           F  
HETATM   15  O4  UNL     1      -0.676   0.943  -0.486  1.00  0.00           O  
HETATM   16  C9  UNL     1       2.155  -0.434   1.116  1.00  0.00           C  
HETATM   17  O5  UNL     1       1.593  -1.046   2.076  1.00  0.00           O  
HETATM   18  N2  UNL     1       3.509  -0.311   1.102  1.00  0.00           N  
HETATM   19  H1  UNL     1       3.837   1.368  -1.708  1.00  0.00           H  
HETATM   20  H2  UNL     1       1.382   1.131  -1.659  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.424  -0.165   1.248  1.00  0.00           H  
HETATM   22  H4  UNL     1      -0.366  -2.248   0.017  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.107  -1.347  -1.569  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.457  -1.438  -1.554  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.670  -2.367   0.561  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.236   0.841  -1.749  1.00  0.00           H  
HETATM   27  H9  UNL     1      -4.635   1.035   1.054  1.00  0.00           H  
HETATM   28  H10 UNL     1       4.103  -0.716   1.877  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   18
CONECT    3    4    4   19
CONECT    4    5   20
CONECT    5    6   16
CONECT    6    7   15   21
CONECT    7    8   22   23
CONECT    8    9   10   24
CONECT    9   25
CONECT   10   11   15   26
CONECT   11   12   13   14
CONECT   12   27
CONECT   16   17   17   18
CONECT   18   28
END

HMDB0257970
     RDKit          3D
1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4...
 28 29  0  0  0  0  0  0  0  0999 V2000
    5.4229    0.4297    0.1187 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1578    0.3262    0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3783    0.8519   -0.8956 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042    0.7130   -0.8579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3778    0.0708    0.1443 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0431   -0.0869    0.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417   -1.3046   -0.5332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0133   -0.9625   -0.6575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6378   -1.3633    0.5140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9800    0.5269   -0.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8580    1.1989    0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1873    0.8786    0.1982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6564    2.5749    0.1515 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4298    0.9002    1.5861 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6759    0.9429   -0.4859 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1554   -0.4341    1.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926   -1.0459    2.0755 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5087   -0.3111    1.1023 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8370    1.3682   -1.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3823    1.1307   -1.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4240   -0.1651    1.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3664   -2.2478    0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1075   -1.3468   -1.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4568   -1.4380   -1.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6703   -2.3671    0.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2359    0.8408   -1.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6355    1.0350    1.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1026   -0.7156    1.8765 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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 10 15  1  0
  5 16  1  0
 16 17  2  0
 16 18  1  0
 18  2  1  0
 15  6  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 18 28  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₉H₁₀F₂N₂O₅

Average Molecular Weight

264.185

Monoisotopic Molecular Weight

264.055777756

IUPAC Name

1-{5-[difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl}-1,2,3,4-tetrahydropyrimidine-2,4-dione

Traditional Name

1-{5-[difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl}-3H-pyrimidine-2,4-dione

CAS Registry Number

Not Available

SMILES

OC1CC(OC1C(O)(F)F)N1C=CC(=O)NC1=O

InChI Identifier

InChI=1S/C9H10F2N2O5/c10-9(11,17)7-4(14)3-6(18-7)13-2-1-5(15)12-8(13)16/h1-2,4,6-7,14,17H,3H2,(H,12,15,16)

InChI Key

DGVFFRFCTNNUCI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Pyrimidones

Alternative Parents

Substituents

Pyrimidone
Hydropyrimidine
Heteroaromatic compound
Vinylogous amide
Tetrahydrofuran
Urea
Secondary alcohol
Lactam
Oxacycle
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Alkyl halide
Alkyl fluoride
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	-0.67	ALOGPS
logP	-0.67	ChemAxon
logS	-0.6	ALOGPS
pKa (Strongest Acidic)	6.15	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.1 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	51.62 m³·mol⁻¹	ChemAxon
Polarizability	21.25 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	150.519	30932474
DeepCCS	[M-H]-	148.161	30932474
DeepCCS	[M-2H]-	181.238	30932474
DeepCCS	[M+Na]+	156.612	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	3.18 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7956 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.39 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	817.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	266.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	92.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	72.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	290.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	280.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	321.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	643.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	191.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	922.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	196.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	198.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	507.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	284.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	162.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione	OC1CC(OC1C(O)(F)F)N1C=CC(=O)NC1=O	2586.4	Standard polar	33892256
1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione	OC1CC(OC1C(O)(F)F)N1C=CC(=O)NC1=O	1941.3	Standard non polar	33892256
1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione	OC1CC(OC1C(O)(F)F)N1C=CC(=O)NC1=O	2263.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione,3TMS,isomer #1	C[Si](C)(C)OC1CC(N2C=CC(=O)N([Si](C)(C)C)C2=O)OC1C(F)(F)O[Si](C)(C)C	2313.8	Semi standard non polar	33892256
1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione,3TMS,isomer #1	C[Si](C)(C)OC1CC(N2C=CC(=O)N([Si](C)(C)C)C2=O)OC1C(F)(F)O[Si](C)(C)C	2283.0	Standard non polar	33892256
1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione,3TMS,isomer #1	C[Si](C)(C)OC1CC(N2C=CC(=O)N([Si](C)(C)C)C2=O)OC1C(F)(F)O[Si](C)(C)C	2229.8	Standard polar	33892256
1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC(N2C=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)OC1C(F)(F)O[Si](C)(C)C(C)(C)C	2990.9	Semi standard non polar	33892256
1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC(N2C=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)OC1C(F)(F)O[Si](C)(C)C(C)(C)C	2866.2	Standard non polar	33892256
1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC(N2C=CC(=O)N([Si](C)(C)C(C)(C)C)C2=O)OC1C(F)(F)O[Si](C)(C)C(C)(C)C	2523.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-9200000000-9fe674afae7418e675fe	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione GC-MS (TBDMS_2_3) - 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

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

156963671

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 1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione (HMDB0257970)

MOL for HMDB0257970 (1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione)

3D MOL for HMDB0257970 (1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione)

3D SDF for HMDB0257970 (1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione)

3D-SDF for HMDB0257970 (1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione)

PDB for HMDB0257970 (1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione)

3D PDB for HMDB0257970 (1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione)

SMILES for HMDB0257970 (1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione)

INCHI for HMDB0257970 (1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione)

Structure for HMDB0257970 (1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione)

3D Structure for HMDB0257970 (1-[(2R,4S,5S)-5-[Difluoro(hydroxy)methyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra