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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:26:20 UTC

Update Date

2022-09-22 17:45:01 UTC

HMDB ID

HMDB0247432

Secondary Accession Numbers

None

Metabolite Identification

Common Name

8-Cyclopentyl-1,3-dipropylxanthine

Description

8-Cyclopentyl-1,3-dipropylxanthine, also known as 1,3-DPCPX or 1,3-dipropyl-8-cyclopentylxanthine, 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-1,3-dipropylxanthine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 8-cyclopentyl-1,3-dipropylxanthine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 8-Cyclopentyl-1,3-dipropylxanthine 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

HMDB0247432
     RDKit          3D
8-Cyclopentyl-1,3-dipropylxanthine
 46 48  0  0  0  0  0  0  0  0999 V2000
   -5.7247   -2.9353   -0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3346   -2.4783    0.1569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8615   -1.4372   -0.8342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5513   -0.9505   -0.5379 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4889   -1.5574   -1.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6209   -2.5607   -1.8094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2134   -1.0951   -0.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0357   -1.4839   -1.1407 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9447   -0.6706   -0.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4240   -0.8320   -0.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0197   -1.0937    0.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3983   -0.4760    0.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1594    0.7890   -0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0638    0.4143   -1.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3104    0.2493    0.1573 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0142    0.0087    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287    0.5966    0.5555 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9717    1.7426    1.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9726    3.0387    0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8052    4.2042    1.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3510    0.1184    0.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3374    0.7073    0.7616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3187   -3.2974    0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1995   -2.0761   -0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5827   -3.7160   -1.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6881   -3.3799    0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3933   -2.0279    1.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5713   -0.5702   -0.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9969   -1.8274   -1.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6557   -1.6730   -1.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1437   -2.1882    0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4395   -0.6434    1.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0677   -1.1131   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8398   -0.3009    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1014    1.0512   -0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8314    1.5995    0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5766    0.2533   -2.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576    1.2632   -1.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7302    1.0124    0.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7449    1.8089    2.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0077    1.7107    1.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9039    3.1876    0.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1218    3.0677   -0.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4390    5.0926    0.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7549    4.4710    2.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0166    3.9969    2.3359 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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  9 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 17 21  1  0
 21 22  2  0
 21  4  1  0
 16  7  2  0
 14 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
M  END


  Mrv1652310211603322D          

 22 24  0  0  0  0            999 V2000
    1.4289   -2.4750    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
    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
   -0.7846    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0945    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5795   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3641    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3641    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5795    1.0799    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  1  0  0  0  0
  5  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  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
  5 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247432

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCN1C2=C(N=C(N2)C2CCCC2)C(=O)N(CCC)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H24N4O2/c1-3-9-19-14-12(15(21)20(10-4-2)16(19)22)17-13(18-14)11-7-5-6-8-11/h11H,3-10H2,1-2H3,(H,17,18)

> <INCHI_KEY>
FFBDFADSZUINTG-UHFFFAOYSA-N

> <FORMULA>
C16H24N4O2

> <MOLECULAR_WEIGHT>
304.394

> <EXACT_MASS>
304.189926029

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
34.818478108637784

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-cyclopentyl-1,3-dipropyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione

> <ALOGPS_LOGP>
3.39

> <JCHEM_LOGP>
2.742020006

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.574744125541162

> <JCHEM_PKA_STRONGEST_BASIC>
2.6160436338821444

> <JCHEM_POLAR_SURFACE_AREA>
69.30000000000001

> <JCHEM_REFRACTIVITY>
83.2119

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dipropylcyclopentylxanthine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247432
     RDKit          3D
8-Cyclopentyl-1,3-dipropylxanthine
 46 48  0  0  0  0  0  0  0  0999 V2000
   -5.7247   -2.9353   -0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3346   -2.4783    0.1569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8615   -1.4372   -0.8342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5513   -0.9505   -0.5379 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4889   -1.5574   -1.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6209   -2.5607   -1.8094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2134   -1.0951   -0.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0357   -1.4839   -1.1407 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9447   -0.6706   -0.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4240   -0.8320   -0.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0197   -1.0937    0.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3983   -0.4760    0.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1594    0.7890   -0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0638    0.4143   -1.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3104    0.2493    0.1573 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0142    0.0087    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287    0.5966    0.5555 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9717    1.7426    1.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9726    3.0387    0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8052    4.2042    1.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3510    0.1184    0.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3374    0.7073    0.7616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3187   -3.2974    0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1995   -2.0761   -0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5827   -3.7160   -1.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6881   -3.3799    0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3933   -2.0279    1.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5713   -0.5702   -0.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9969   -1.8274   -1.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6557   -1.6730   -1.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1437   -2.1882    0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4395   -0.6434    1.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0677   -1.1131   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8398   -0.3009    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1014    1.0512   -0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8314    1.5995    0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5766    0.2533   -2.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576    1.2632   -1.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7302    1.0124    0.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7449    1.8089    2.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0077    1.7107    1.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9039    3.1876    0.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1218    3.0677   -0.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4390    5.0926    0.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7549    4.4710    2.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0166    3.9969    2.3359 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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  9 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 17 21  1  0
 21 22  2  0
 21  4  1  0
 16  7  2  0
 14 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
M  END

HEADER    PROTEIN                                 21-OCT-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-OCT-16         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -0.770   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       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -1.465   2.016   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -2.370   0.770   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -1.465  -0.476   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -3.910   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.815  -0.476   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.280   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.280   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.815   2.016   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6   17                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    6   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16    5                                                       
CONECT   18   16   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0247432
HETATM    1  C1  UNL     1      -5.725  -2.935  -0.233  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.335  -2.478   0.157  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.862  -1.437  -0.834  1.00  0.00           C  
HETATM    4  N1  UNL     1      -2.551  -0.950  -0.538  1.00  0.00           N  
HETATM    5  C4  UNL     1      -1.489  -1.557  -1.057  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.621  -2.561  -1.809  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.213  -1.095  -0.777  1.00  0.00           C  
HETATM    8  N2  UNL     1       1.036  -1.484  -1.141  1.00  0.00           N  
HETATM    9  C6  UNL     1       1.945  -0.671  -0.575  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.424  -0.832  -0.779  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.020  -1.094   0.587  1.00  0.00           C  
HETATM   12  C9  UNL     1       5.398  -0.476   0.496  1.00  0.00           C  
HETATM   13  C10 UNL     1       5.159   0.789  -0.303  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.064   0.414  -1.301  1.00  0.00           C  
HETATM   15  N3  UNL     1       1.310   0.249   0.157  1.00  0.00           N  
HETATM   16  C12 UNL     1      -0.014   0.009   0.048  1.00  0.00           C  
HETATM   17  N4  UNL     1      -1.129   0.597   0.555  1.00  0.00           N  
HETATM   18  C13 UNL     1      -0.972   1.743   1.415  1.00  0.00           C  
HETATM   19  C14 UNL     1      -0.973   3.039   0.628  1.00  0.00           C  
HETATM   20  C15 UNL     1      -0.805   4.204   1.577  1.00  0.00           C  
HETATM   21  C16 UNL     1      -2.351   0.118   0.261  1.00  0.00           C  
HETATM   22  O2  UNL     1      -3.337   0.707   0.762  1.00  0.00           O  
HETATM   23  H1  UNL     1      -6.319  -3.297   0.611  1.00  0.00           H  
HETATM   24  H2  UNL     1      -6.199  -2.076  -0.764  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.583  -3.716  -1.028  1.00  0.00           H  
HETATM   26  H4  UNL     1      -3.688  -3.380   0.149  1.00  0.00           H  
HETATM   27  H5  UNL     1      -4.393  -2.028   1.181  1.00  0.00           H  
HETATM   28  H6  UNL     1      -4.571  -0.570  -0.726  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.997  -1.827  -1.844  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.656  -1.673  -1.429  1.00  0.00           H  
HETATM   31  H9  UNL     1       4.144  -2.188   0.724  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.439  -0.643   1.399  1.00  0.00           H  
HETATM   33  H11 UNL     1       6.068  -1.113  -0.124  1.00  0.00           H  
HETATM   34  H12 UNL     1       5.840  -0.301   1.476  1.00  0.00           H  
HETATM   35  H13 UNL     1       6.101   1.051  -0.804  1.00  0.00           H  
HETATM   36  H14 UNL     1       4.831   1.599   0.377  1.00  0.00           H  
HETATM   37  H15 UNL     1       4.577   0.253  -2.276  1.00  0.00           H  
HETATM   38  H16 UNL     1       3.358   1.263  -1.427  1.00  0.00           H  
HETATM   39  H17 UNL     1       1.730   1.012   0.712  1.00  0.00           H  
HETATM   40  H18 UNL     1      -1.745   1.809   2.198  1.00  0.00           H  
HETATM   41  H19 UNL     1       0.008   1.711   1.954  1.00  0.00           H  
HETATM   42  H20 UNL     1      -1.904   3.188   0.053  1.00  0.00           H  
HETATM   43  H21 UNL     1      -0.122   3.068  -0.090  1.00  0.00           H  
HETATM   44  H22 UNL     1      -0.439   5.093   0.991  1.00  0.00           H  
HETATM   45  H23 UNL     1      -1.755   4.471   2.057  1.00  0.00           H  
HETATM   46  H24 UNL     1      -0.017   3.997   2.336  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   28   29
CONECT    4    5   21
CONECT    5    6    6    7
CONECT    7    8   16   16
CONECT    8    9    9
CONECT    9   10   15
CONECT   10   11   14   30
CONECT   11   12   31   32
CONECT   12   13   33   34
CONECT   13   14   35   36
CONECT   14   37   38
CONECT   15   16   39
CONECT   16   17
CONECT   17   18   21
CONECT   18   19   40   41
CONECT   19   20   42   43
CONECT   20   44   45   46
CONECT   21   22   22
END

HMDB0247432
     RDKit          3D
8-Cyclopentyl-1,3-dipropylxanthine
 46 48  0  0  0  0  0  0  0  0999 V2000
   -5.7247   -2.9353   -0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3346   -2.4783    0.1569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8615   -1.4372   -0.8342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5513   -0.9505   -0.5379 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4889   -1.5574   -1.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6209   -2.5607   -1.8094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2134   -1.0951   -0.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0357   -1.4839   -1.1407 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9447   -0.6706   -0.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4240   -0.8320   -0.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0197   -1.0937    0.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3983   -0.4760    0.4962 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1594    0.7890   -0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0638    0.4143   -1.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3104    0.2493    0.1573 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0142    0.0087    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287    0.5966    0.5555 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9717    1.7426    1.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9726    3.0387    0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8052    4.2042    1.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3510    0.1184    0.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3374    0.7073    0.7616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3187   -3.2974    0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1995   -2.0761   -0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5827   -3.7160   -1.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6881   -3.3799    0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3933   -2.0279    1.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5713   -0.5702   -0.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9969   -1.8274   -1.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6557   -1.6730   -1.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1437   -2.1882    0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4395   -0.6434    1.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0677   -1.1131   -0.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8398   -0.3009    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1014    1.0512   -0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8314    1.5995    0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5766    0.2533   -2.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576    1.2632   -1.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7302    1.0124    0.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7449    1.8089    2.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0077    1.7107    1.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9039    3.1876    0.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1218    3.0677   -0.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4390    5.0926    0.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7549    4.4710    2.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0166    3.9969    2.3359 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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  9 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 17 21  1  0
 21 22  2  0
 21  4  1  0
 16  7  2  0
 14 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,3-Dipropyl-8-cyclopentylxanthine	ChEBI
1,3-DPCPX	ChEBI
CPX	ChEBI
Dipropylcyclopentylxanthine	ChEBI
PD-116,948	ChEBI
PD-116948	ChEBI
8-Cyclopentyl-3,7-dihydro-1,3-dipropyl-1H-purin-2,6-dione	HMDB
8-Cyclopentyl-1,3-dipropylxanthine	ChEBI

Chemical Formula

C₁₆H₂₄N₄O₂

Average Molecular Weight

304.394

Monoisotopic Molecular Weight

304.189926029

IUPAC Name

8-cyclopentyl-1,3-dipropyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione

Traditional Name

dipropylcyclopentylxanthine

CAS Registry Number

Not Available

SMILES

CCCN1C2=C(N=C(N2)C2CCCC2)C(=O)N(CCC)C1=O

InChI Identifier

InChI=1S/C16H24N4O2/c1-3-9-19-14-12(15(21)20(10-4-2)16(19)22)17-13(18-14)11-7-5-6-8-11/h11H,3-10H2,1-2H3,(H,17,18)

InChI Key

FFBDFADSZUINTG-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
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxopurine (CHEBI:73282 )

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	3.39	ALOGPS
logP	2.74	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	11.57	ChemAxon
pKa (Strongest Basic)	2.62	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	5	ChemAxon
Refractivity	83.21 m³·mol⁻¹	ChemAxon
Polarizability	34.82 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]+	175.615	30932474
DeepCCS	[M-H]-	173.257	30932474
DeepCCS	[M-2H]-	206.143	30932474
DeepCCS	[M+Na]+	181.708	30932474
AllCCS	[M+H]+	171.9	32859911
AllCCS	[M+H-H2O]+	168.9	32859911
AllCCS	[M+NH4]+	174.7	32859911
AllCCS	[M+Na]+	175.5	32859911
AllCCS	[M-H]-	173.0	32859911
AllCCS	[M+Na-2H]-	173.0	32859911
AllCCS	[M+HCOO]-	173.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Cyclopentyl-1,3-dipropylxanthine	CCCN1C2=C(N=C(N2)C2CCCC2)C(=O)N(CCC)C1=O	3221.9	Standard polar	33892256
8-Cyclopentyl-1,3-dipropylxanthine	CCCN1C2=C(N=C(N2)C2CCCC2)C(=O)N(CCC)C1=O	2603.0	Standard non polar	33892256
8-Cyclopentyl-1,3-dipropylxanthine	CCCN1C2=C(N=C(N2)C2CCCC2)C(=O)N(CCC)C1=O	2539.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Cyclopentyl-1,3-dipropylxanthine,1TMS,isomer #1	CCCN1C(=O)C2=C(N([Si](C)(C)C)C(C3CCCC3)=N2)N(CCC)C1=O	2538.3	Semi standard non polar	33892256
8-Cyclopentyl-1,3-dipropylxanthine,1TMS,isomer #1	CCCN1C(=O)C2=C(N([Si](C)(C)C)C(C3CCCC3)=N2)N(CCC)C1=O	2607.6	Standard non polar	33892256
8-Cyclopentyl-1,3-dipropylxanthine,1TMS,isomer #1	CCCN1C(=O)C2=C(N([Si](C)(C)C)C(C3CCCC3)=N2)N(CCC)C1=O	3340.5	Standard polar	33892256
8-Cyclopentyl-1,3-dipropylxanthine,1TBDMS,isomer #1	CCCN1C(=O)C2=C(N([Si](C)(C)C(C)(C)C)C(C3CCCC3)=N2)N(CCC)C1=O	2683.8	Semi standard non polar	33892256
8-Cyclopentyl-1,3-dipropylxanthine,1TBDMS,isomer #1	CCCN1C(=O)C2=C(N([Si](C)(C)C(C)(C)C)C(C3CCCC3)=N2)N(CCC)C1=O	2830.1	Standard non polar	33892256
8-Cyclopentyl-1,3-dipropylxanthine,1TBDMS,isomer #1	CCCN1C(=O)C2=C(N([Si](C)(C)C(C)(C)C)C(C3CCCC3)=N2)N(CCC)C1=O	3386.5	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-1,3-dipropylxanthine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01t9-1190000000-d206dc4a175f584b34ab	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine , positive-QTOF	splash10-00fr-3891000000-282be93d6a4f82333c33	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 10V, Positive-QTOF	splash10-0a4i-0039000000-2b4e1e54df86f28f7e51	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 20V, Positive-QTOF	splash10-03di-2191000000-de6778fefa6b6103af7e	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 40V, Positive-QTOF	splash10-0006-9540000000-02bdb2babcc0d8e976b6	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 10V, Negative-QTOF	splash10-0udi-0059000000-7fb897a6ec851c8892f1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 20V, Negative-QTOF	splash10-0ik9-0294000000-602d9f5f88dad43a57f8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 40V, Negative-QTOF	splash10-014i-8790000000-8675dd5df97ca5fcadaf	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 10V, Positive-QTOF	splash10-0a4i-0009000000-8afd581d108fc4ab5bbf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 20V, Positive-QTOF	splash10-0a4i-0019000000-40b8fad5b5cd148bf890	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 40V, Positive-QTOF	splash10-0gir-0492000000-0dfafda85c08bc9e0b9d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 10V, Negative-QTOF	splash10-0udi-0009000000-b3ce92e14ecef0f640db	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 20V, Negative-QTOF	splash10-0udi-0139000000-0de5f9b3dbe2c1f94e72	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 40V, Negative-QTOF	splash10-00r6-4590000000-813b85b7d0affa982ab1	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

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
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB12946

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

1289

KEGG Compound ID

C13709

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dipropylcyclopentylxanthine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

73282

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-1,3-dipropylxanthine (HMDB0247432)

MOL for HMDB0247432 (8-Cyclopentyl-1,3-dipropylxanthine)

3D MOL for HMDB0247432 (8-Cyclopentyl-1,3-dipropylxanthine)

3D SDF for HMDB0247432 (8-Cyclopentyl-1,3-dipropylxanthine)

3D-SDF for HMDB0247432 (8-Cyclopentyl-1,3-dipropylxanthine)

PDB for HMDB0247432 (8-Cyclopentyl-1,3-dipropylxanthine)

3D PDB for HMDB0247432 (8-Cyclopentyl-1,3-dipropylxanthine)

SMILES for HMDB0247432 (8-Cyclopentyl-1,3-dipropylxanthine)

INCHI for HMDB0247432 (8-Cyclopentyl-1,3-dipropylxanthine)

Structure for HMDB0247432 (8-Cyclopentyl-1,3-dipropylxanthine)

3D Structure for HMDB0247432 (8-Cyclopentyl-1,3-dipropylxanthine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra