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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-12 00:30:25 UTC

Update Date

2021-09-26 23:18:25 UTC

HMDB ID

HMDB0260333

Secondary Accession Numbers

None

Metabolite Identification

Common Name

8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione

Description

8-cyclopentyl-3-(3-fluoropropyl)-1-propyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Based on a literature review very few articles have been published on 8-cyclopentyl-3-(3-fluoropropyl)-1-propyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione. This compound has been identified in human blood as reported by (PMID: 31557052 ). 8-cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-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

HMDB0260333
     RDKit          3D
8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione
 46 48  0  0  0  0  0  0  0  0999 V2000
   -3.3744   -3.4075   -0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3070   -2.3591   -0.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6504   -1.5677    1.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4585   -0.8710    0.6325 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2452   -1.4061    0.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1203   -2.5406    1.2607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1085   -0.7294    0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2140   -0.9506    0.3868 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8671    0.1018   -0.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3202    0.2746   -0.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0234    0.1590    1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9418   -1.0178    0.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2900   -0.9827   -0.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9045   -0.8042   -1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9456    1.0212   -0.4525 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2702    0.5313   -0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4959    1.0784   -0.2906 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7868    4.8862   -1.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5632    5.5420    0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309122102302D          

 23 25  0  0  0  0            999 V2000
    4.2135    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0701    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    4.8229    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0260333

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCN1C(=O)N(CCCF)C2=C(NC(=N2)C2CCCC2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H23FN4O2/c1-2-9-21-15(22)12-14(20(16(21)23)10-5-8-17)19-13(18-12)11-6-3-4-7-11/h11H,2-10H2,1H3,(H,18,19)

> <INCHI_KEY>
GGGMDKJPUXTDAW-UHFFFAOYSA-N

> <FORMULA>
C16H23FN4O2

> <MOLECULAR_WEIGHT>
322.384

> <EXACT_MASS>
322.18050416

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
34.82523018404605

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-cyclopentyl-3-(3-fluoropropyl)-1-propyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
2.162956476666665

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.011727212267004

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5439161534694953

> <JCHEM_POLAR_SURFACE_AREA>
69.30000000000001

> <JCHEM_REFRACTIVITY>
84.71459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-cyclopentyl-3-(3-fluoropropyl)-1-propyl-7H-purine-2,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0260333
     RDKit          3D
8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione
 46 48  0  0  0  0  0  0  0  0999 V2000
   -3.3744   -3.4075   -0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3070   -2.3591   -0.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6504   -1.5677    1.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4585   -0.8710    0.6325 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2452   -1.4061    0.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1203   -2.5406    1.2607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1085   -0.7294    0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2140   -0.9506    0.3868 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8671    0.1018   -0.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3202    0.2746   -0.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0234    0.1590    1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9418   -1.0178    0.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2900   -0.9827   -0.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9045   -0.8042   -1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9456    1.0212   -0.4525 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2702    0.5313   -0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4959    1.0784   -0.2906 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5920    2.4084   -0.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5228    3.4044    0.2628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6238    4.7893   -0.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8246    4.8819   -1.0098 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5579    0.3772    0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7058    0.8871   -0.0383 O   0  0  0  0  0  0  0  0  0  0  0  0
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 20 45  1  0
 20 46  1  0
M  END

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-21         0                                  
HETATM    1  C   UNK     0       7.865   1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       3.864   2.073   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.530  -0.237   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.268   4.089   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -0.268   1.597   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.618   1.597   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.083   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.083   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.618   4.089   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       2.530   4.383   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.530   5.923   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.864   6.693   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.864   8.233   0.000  0.00  0.00           C+0
HETATM   23  F   UNK     0       5.198   9.003   0.000  0.00  0.00           F+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   11                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    7                                                       
CONECT   12   10   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17    8   18   20                                                  
CONECT   18   17    4   19                                                  
CONECT   19   18                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0260333
HETATM    1  C1  UNL     1      -3.374  -3.408  -0.585  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.307  -2.359  -0.064  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.650  -1.568   1.012  1.00  0.00           C  
HETATM    4  N1  UNL     1      -2.459  -0.871   0.633  1.00  0.00           N  
HETATM    5  C4  UNL     1      -1.245  -1.406   0.774  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.120  -2.541   1.261  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.109  -0.729   0.391  1.00  0.00           C  
HETATM    8  N2  UNL     1       1.214  -0.951   0.387  1.00  0.00           N  
HETATM    9  C6  UNL     1       1.867   0.102  -0.122  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.320   0.275  -0.309  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.023   0.159   1.019  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.942  -1.018   0.883  1.00  0.00           C  
HETATM   13  C10 UNL     1       5.290  -0.983  -0.592  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.905  -0.804  -1.207  1.00  0.00           C  
HETATM   15  N3  UNL     1       0.946   1.021  -0.452  1.00  0.00           N  
HETATM   16  C12 UNL     1      -0.270   0.531  -0.146  1.00  0.00           C  
HETATM   17  N4  UNL     1      -1.496   1.078  -0.291  1.00  0.00           N  
HETATM   18  C13 UNL     1      -1.592   2.408  -0.863  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.523   3.404   0.263  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.624   4.789  -0.344  1.00  0.00           C  
HETATM   21  F1  UNL     1      -2.825   4.882  -1.010  1.00  0.00           F  
HETATM   22  C16 UNL     1      -2.558   0.377   0.096  1.00  0.00           C  
HETATM   23  O2  UNL     1      -3.706   0.887  -0.038  1.00  0.00           O  
HETATM   24  H1  UNL     1      -3.881  -4.061  -1.352  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.484  -2.960  -1.054  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.063  -4.123   0.202  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.684  -1.684  -0.858  1.00  0.00           H  
HETATM   28  H5  UNL     1      -5.218  -2.904   0.298  1.00  0.00           H  
HETATM   29  H6  UNL     1      -3.493  -2.195   1.940  1.00  0.00           H  
HETATM   30  H7  UNL     1      -4.415  -0.811   1.360  1.00  0.00           H  
HETATM   31  H8  UNL     1       1.627  -1.850   0.747  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.595   1.235  -0.749  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.289  -0.027   1.825  1.00  0.00           H  
HETATM   34  H11 UNL     1       4.563   1.098   1.295  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.344  -1.931   1.071  1.00  0.00           H  
HETATM   36  H13 UNL     1       5.806  -0.909   1.541  1.00  0.00           H  
HETATM   37  H14 UNL     1       5.833  -0.034  -0.783  1.00  0.00           H  
HETATM   38  H15 UNL     1       5.800  -1.878  -0.944  1.00  0.00           H  
HETATM   39  H16 UNL     1       3.324  -1.740  -1.173  1.00  0.00           H  
HETATM   40  H17 UNL     1       3.991  -0.467  -2.259  1.00  0.00           H  
HETATM   41  H18 UNL     1      -0.732   2.534  -1.567  1.00  0.00           H  
HETATM   42  H19 UNL     1      -2.565   2.484  -1.381  1.00  0.00           H  
HETATM   43  H20 UNL     1      -2.358   3.209   0.954  1.00  0.00           H  
HETATM   44  H21 UNL     1      -0.581   3.307   0.819  1.00  0.00           H  
HETATM   45  H22 UNL     1      -0.787   4.886  -1.083  1.00  0.00           H  
HETATM   46  H23 UNL     1      -1.563   5.542   0.453  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29   30
CONECT    4    5   22
CONECT    5    6    6    7
CONECT    7    8   16   16
CONECT    8    9   31
CONECT    9   10   15   15
CONECT   10   11   14   32
CONECT   11   12   33   34
CONECT   12   13   35   36
CONECT   13   14   37   38
CONECT   14   39   40
CONECT   15   16
CONECT   16   17
CONECT   17   18   22
CONECT   18   19   41   42
CONECT   19   20   43   44
CONECT   20   21   45   46
CONECT   22   23   23
END

HMDB0260333
     RDKit          3D
8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione
 46 48  0  0  0  0  0  0  0  0999 V2000
   -3.3744   -3.4075   -0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3070   -2.3591   -0.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6504   -1.5677    1.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4585   -0.8710    0.6325 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2452   -1.4061    0.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1203   -2.5406    1.2607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1085   -0.7294    0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2140   -0.9506    0.3868 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8671    0.1018   -0.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3202    0.2746   -0.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0234    0.1590    1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9418   -1.0178    0.8830 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2900   -0.9827   -0.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9045   -0.8042   -1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9456    1.0212   -0.4525 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2702    0.5313   -0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4959    1.0784   -0.2906 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5920    2.4084   -0.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5228    3.4044    0.2628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6238    4.7893   -0.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8246    4.8819   -1.0098 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5579    0.3772    0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7058    0.8871   -0.0383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8811   -4.0610   -1.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4837   -2.9602   -1.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0631   -4.1227    0.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6839   -1.6835   -0.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2175   -2.9035    0.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4927   -2.1953    1.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4145   -0.8109    1.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6271   -1.8497    0.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5954    1.2355   -0.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2894   -0.0269    1.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5628    1.0980    1.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3442   -1.9312    1.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8057   -0.9086    1.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8332   -0.0340   -0.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8000   -1.8785   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3244   -1.7403   -1.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9906   -0.4673   -2.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7315    2.5344   -1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5655    2.4836   -1.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3576    3.2088    0.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5811    3.3071    0.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7868    4.8862   -1.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5632    5.5420    0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  9 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17 22  1  0
 22 23  2  0
 22  4  1  0
 16  7  2  0
 14 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₂₃FN₄O₂

Average Molecular Weight

322.384

Monoisotopic Molecular Weight

322.18050416

IUPAC Name

8-cyclopentyl-3-(3-fluoropropyl)-1-propyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

Traditional Name

8-cyclopentyl-3-(3-fluoropropyl)-1-propyl-7H-purine-2,6-dione

CAS Registry Number

Not Available

SMILES

CCCN1C(=O)N(CCCF)C2=C(NC(=N2)C2CCCC2)C1=O

InChI Identifier

InChI=1S/C16H23FN4O2/c1-2-9-21-15(22)12-14(20(16(21)23)10-5-8-17)19-13(18-12)11-6-3-4-7-11/h11H,2-10H2,1H3,(H,18,19)

InChI Key

GGGMDKJPUXTDAW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Xanthines

Alternative Parents

Substituents

Xanthine
6-oxopurine
Purinone
Alkaloid or derivatives
Pyrimidone
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Lactam
Urea
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Organic nitrogen compound
Organic oxide
Organic oxygen compound
Alkyl halide
Alkyl fluoride
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.57	ALOGPS
logP	2.16	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.01	ChemAxon
pKa (Strongest Basic)	-0.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.3 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.71 m³·mol⁻¹	ChemAxon
Polarizability	34.83 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	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	173.176	32859911
AllCCS	[M+H-H2O]+	170.296	32859911
AllCCS	[M+Na]+	176.598	32859911
AllCCS	[M+NH4]+	175.836	32859911
AllCCS	[M-H]-	174.104	32859911
AllCCS	[M+Na-2H]-	174.089	32859911
AllCCS	[M+HCOO]-	174.197	32859911
DeepCCS	[M+H]+	178.337	30932474
DeepCCS	[M-H]-	175.979	30932474
DeepCCS	[M-2H]-	208.865	30932474
DeepCCS	[M+Na]+	184.43	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione	CCCN1C(=O)N(CCCF)C2=C(NC(=N2)C2CCCC2)C1=O	3082.9	Standard polar	33892256
8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione	CCCN1C(=O)N(CCCF)C2=C(NC(=N2)C2CCCC2)C1=O	2669.1	Standard non polar	33892256
8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione	CCCN1C(=O)N(CCCF)C2=C(NC(=N2)C2CCCC2)C1=O	2547.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione,1TMS,isomer #1	CCCN1C(=O)C2=C(N=C(C3CCCC3)N2[Si](C)(C)C)N(CCCF)C1=O	2573.2	Semi standard non polar	33892256
8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione,1TMS,isomer #1	CCCN1C(=O)C2=C(N=C(C3CCCC3)N2[Si](C)(C)C)N(CCCF)C1=O	2631.5	Standard non polar	33892256
8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione,1TMS,isomer #1	CCCN1C(=O)C2=C(N=C(C3CCCC3)N2[Si](C)(C)C)N(CCCF)C1=O	3221.2	Standard polar	33892256
8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione,1TBDMS,isomer #1	CCCN1C(=O)C2=C(N=C(C3CCCC3)N2[Si](C)(C)C(C)(C)C)N(CCCF)C1=O	2728.0	Semi standard non polar	33892256
8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione,1TBDMS,isomer #1	CCCN1C(=O)C2=C(N=C(C3CCCC3)N2[Si](C)(C)C(C)(C)C)N(CCCF)C1=O	2855.3	Standard non polar	33892256
8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione,1TBDMS,isomer #1	CCCN1C(=O)C2=C(N=C(C3CCCC3)N2[Si](C)(C)C(C)(C)C)N(CCCF)C1=O	3287.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-2092000000-b4fec5ac7c486f56bd21	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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

8217366

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10041802

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione (HMDB0260333)

MOL for HMDB0260333 (8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione)

3D MOL for HMDB0260333 (8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione)

3D SDF for HMDB0260333 (8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione)

3D-SDF for HMDB0260333 (8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione)

PDB for HMDB0260333 (8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione)

3D PDB for HMDB0260333 (8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione)

SMILES for HMDB0260333 (8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione)

INCHI for HMDB0260333 (8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione)

Structure for HMDB0260333 (8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione)

3D Structure for HMDB0260333 (8-Cyclopentyl-3-(3-fluoro-propyl)-1-propyl-3,7-dihydro-purine-2,6-dione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra