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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 20:11:04 UTC

Update Date

2021-09-26 22:50:33 UTC

HMDB ID

HMDB0243498

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1-(3-Carboxypropyl)-3,7-dimethylxanthine

Description

1-(3-Carboxypropyl)-3,7-dimethylxanthine, also known as 3,7-dimetyl -1(3-carboxypropyl)xanthine or CP DMX II, 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 1-(3-Carboxypropyl)-3,7-dimethylxanthine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1-(3-carboxypropyl)-3,7-dimethylxanthine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1-(3-Carboxypropyl)-3,7-dimethylxanthine 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

HMDB0243498
     RDKit          3D
1-(3-Carboxypropyl)-3,7-dimethylxanthine
 33 34  0  0  0  0  0  0  0  0999 V2000
   -3.3018   -2.0981    1.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0629   -0.7411    1.0218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8388    0.3407    1.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2189    1.3637    0.6360 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0719    0.9649    0.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9689   -0.3846    0.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8666   -1.0456   -0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7452   -2.2869    0.0181 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1049   -0.4338   -0.8985 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2563   -1.1410   -1.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096   -1.1842   -0.4695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9549    0.1417   -0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0892   -0.0373    0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4472   -1.1900    1.1964 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7570    1.0552    1.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0181    0.8867   -1.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8498    1.5261   -1.7783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0962    1.5644   -0.6496 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1768    2.9864   -0.9248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7653   -2.2807    2.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9329   -2.8039    0.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3860   -2.2482    1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7846    0.3369    1.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5940   -0.6919   -2.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9835   -2.2052   -1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1475   -1.7494    0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2344   -1.7590   -0.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1979    0.7539    0.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3372    0.7229   -0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4088    1.6177    0.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2651    3.4944   -0.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1979    3.0816   -2.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0744    3.4433   -0.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
  9 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
  6  2  1  0
 18  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 15 30  1  0
 19 31  1  0
 19 32  1  0
 19 33  1  0
M  END


  Mrv1652306031607152D          

 19 20  0  0  0  0            999 V2000
    6.0409    2.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2708    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7859    4.7924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7859    3.4576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  7  4  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 12  6  2  0  0  0  0
 12  9  1  0  0  0  0
 13  1  1  0  0  0  0
 13  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  2  1  0  0  0  0
 14  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15  5  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16  7  2  0  0  0  0
 17  7  1  0  0  0  0
 18 10  2  0  0  0  0
 19 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0243498

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C=NC2=C1C(=O)N(CCCC(O)=O)C(=O)N2C

> <INCHI_IDENTIFIER>
InChI=1S/C11H14N4O4/c1-13-6-12-9-8(13)10(18)15(11(19)14(9)2)5-3-4-7(16)17/h6H,3-5H2,1-2H3,(H,16,17)

> <INCHI_KEY>
WKASGTGXOGALBG-UHFFFAOYSA-N

> <FORMULA>
C11H14N4O4

> <MOLECULAR_WEIGHT>
266.257

> <EXACT_MASS>
266.101504947

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.01893212780987

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)butanoic acid

> <ALOGPS_LOGP>
-0.57

> <JCHEM_LOGP>
-0.5419883419999996

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7607538831735554

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9271215144224699

> <JCHEM_POLAR_SURFACE_AREA>
95.74000000000001

> <JCHEM_REFRACTIVITY>
65.3702

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(3,7-dimethyl-2,6-dioxopurin-1-yl)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0243498
     RDKit          3D
1-(3-Carboxypropyl)-3,7-dimethylxanthine
 33 34  0  0  0  0  0  0  0  0999 V2000
   -3.3018   -2.0981    1.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0629   -0.7411    1.0218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8388    0.3407    1.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2189    1.3637    0.6360 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0719    0.9649    0.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9689   -0.3846    0.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8666   -1.0456   -0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7452   -2.2869    0.0181 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1049   -0.4338   -0.8985 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2563   -1.1410   -1.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096   -1.1842   -0.4695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9549    0.1417   -0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0892   -0.0373    0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4472   -1.1900    1.1964 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7570    1.0552    1.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0181    0.8867   -1.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8498    1.5261   -1.7783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0962    1.5644   -0.6496 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1768    2.9864   -0.9248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7653   -2.2807    2.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9329   -2.8039    0.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3860   -2.2482    1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7846    0.3369    1.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5940   -0.6919   -2.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9835   -2.2052   -1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1475   -1.7494    0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2344   -1.7590   -0.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1979    0.7539    0.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3372    0.7229   -0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4088    1.6177    0.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2651    3.4944   -0.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1979    3.0816   -2.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0744    3.4433   -0.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
  9 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
  6  2  1  0
 18  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 15 30  1  0
 19 31  1  0
 19 32  1  0
 19 33  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      11.276   4.989   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.706   7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      10.800   8.946   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0      10.800   6.454   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       8.002   9.240   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       6.668   6.930   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334   8.470   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   14                                                            
CONECT    3    4    5                                                       
CONECT    4    3    7                                                       
CONECT    5    3   15                                                       
CONECT    6   12   13                                                       
CONECT    7    4   16   17                                                  
CONECT    8    9   10   13                                                  
CONECT    9    8   12   14                                                  
CONECT   10    8   15   18                                                  
CONECT   11   14   15   19                                                  
CONECT   12    6    9                                                       
CONECT   13    1    6    8                                                  
CONECT   14    2    9   11                                                  
CONECT   15    5   10   11                                                  
CONECT   16    7                                                            
CONECT   17    7                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0243498
HETATM    1  C1  UNL     1      -3.302  -2.098   1.469  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.063  -0.741   1.022  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.839   0.341   1.230  1.00  0.00           C  
HETATM    4  N2  UNL     1      -3.219   1.364   0.636  1.00  0.00           N  
HETATM    5  C3  UNL     1      -2.072   0.965   0.056  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.969  -0.385   0.302  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.867  -1.046  -0.192  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.745  -2.287   0.018  1.00  0.00           O  
HETATM    9  N3  UNL     1       0.105  -0.434  -0.898  1.00  0.00           N  
HETATM   10  C6  UNL     1       1.256  -1.141  -1.414  1.00  0.00           C  
HETATM   11  C7  UNL     1       2.410  -1.184  -0.469  1.00  0.00           C  
HETATM   12  C8  UNL     1       2.955   0.142  -0.068  1.00  0.00           C  
HETATM   13  C9  UNL     1       4.089  -0.037   0.865  1.00  0.00           C  
HETATM   14  O2  UNL     1       4.447  -1.190   1.196  1.00  0.00           O  
HETATM   15  O3  UNL     1       4.757   1.055   1.375  1.00  0.00           O  
HETATM   16  C10 UNL     1      -0.018   0.887  -1.126  1.00  0.00           C  
HETATM   17  O4  UNL     1       0.850   1.526  -1.778  1.00  0.00           O  
HETATM   18  N4  UNL     1      -1.096   1.564  -0.650  1.00  0.00           N  
HETATM   19  C11 UNL     1      -1.177   2.986  -0.925  1.00  0.00           C  
HETATM   20  H1  UNL     1      -2.765  -2.281   2.424  1.00  0.00           H  
HETATM   21  H2  UNL     1      -2.933  -2.804   0.685  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.386  -2.248   1.654  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.785   0.337   1.783  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.594  -0.692  -2.382  1.00  0.00           H  
HETATM   25  H6  UNL     1       0.983  -2.205  -1.642  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.147  -1.749   0.459  1.00  0.00           H  
HETATM   27  H8  UNL     1       3.234  -1.759  -0.946  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.198   0.754   0.485  1.00  0.00           H  
HETATM   29  H10 UNL     1       3.337   0.723  -0.939  1.00  0.00           H  
HETATM   30  H11 UNL     1       5.409   1.618   0.816  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.265   3.494  -0.505  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.198   3.082  -2.039  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.074   3.443  -0.505  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    6
CONECT    3    4    4   23
CONECT    4    5
CONECT    5    6    6   18
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   16
CONECT   10   11   24   25
CONECT   11   12   26   27
CONECT   12   13   28   29
CONECT   13   14   14   15
CONECT   15   30
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   31   32   33
END

HMDB0243498
     RDKit          3D
1-(3-Carboxypropyl)-3,7-dimethylxanthine
 33 34  0  0  0  0  0  0  0  0999 V2000
   -3.3018   -2.0981    1.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0629   -0.7411    1.0218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8388    0.3407    1.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2189    1.3637    0.6360 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0719    0.9649    0.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9689   -0.3846    0.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8666   -1.0456   -0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7452   -2.2869    0.0181 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1049   -0.4338   -0.8985 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2563   -1.1410   -1.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096   -1.1842   -0.4695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9549    0.1417   -0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0892   -0.0373    0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4472   -1.1900    1.1964 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7570    1.0552    1.3751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0181    0.8867   -1.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8498    1.5261   -1.7783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0962    1.5644   -0.6496 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1768    2.9864   -0.9248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7653   -2.2807    2.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9329   -2.8039    0.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3860   -2.2482    1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7846    0.3369    1.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5940   -0.6919   -2.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9835   -2.2052   -1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1475   -1.7494    0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2344   -1.7590   -0.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1979    0.7539    0.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3372    0.7229   -0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4088    1.6177    0.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2651    3.4944   -0.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1979    3.0816   -2.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0744    3.4433   -0.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
  9 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
  6  2  1  0
 18  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 15 30  1  0
 19 31  1  0
 19 32  1  0
 19 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3,7-Dimetyl -1(3-carboxypropyl)xanthine	HMDB
1-(3'-Carboxypropyl)-3,7-dimethylxanthine	HMDB
CP DMX II	HMDB
1-(3'-Carboxypropyl)-3,7-dimethylxanthine, sodium salt	HMDB
1-[4-Carboxypropyl]-37-dimethylxanthine (metabolite-V)	HMDB
4-(3,7-Dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)butanoate	HMDB

Chemical Formula

C₁₁H₁₄N₄O₄

Average Molecular Weight

266.257

Monoisotopic Molecular Weight

266.101504947

IUPAC Name

4-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)butanoic acid

Traditional Name

4-(3,7-dimethyl-2,6-dioxopurin-1-yl)butanoic acid

CAS Registry Number

Not Available

SMILES

CN1C=NC2=C1C(=O)N(CCCC(O)=O)C(=O)N2C

InChI Identifier

InChI=1S/C11H14N4O4/c1-13-6-12-9-8(13)10(18)15(11(19)14(9)2)5-3-4-7(16)17/h6H,3-5H2,1-2H3,(H,16,17)

InChI Key

WKASGTGXOGALBG-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
N-substituted imidazole
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Lactam
Urea
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.57	ALOGPS
logP	-0.54	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.76	ChemAxon
pKa (Strongest Basic)	-0.93	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	95.74 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	65.37 m³·mol⁻¹	ChemAxon
Polarizability	26.02 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]+	152.48	30932474
DeepCCS	[M-H]-	150.122	30932474
DeepCCS	[M-2H]-	184.362	30932474
DeepCCS	[M+Na]+	159.288	30932474
AllCCS	[M+H]+	158.0	32859911
AllCCS	[M+H-H2O]+	154.6	32859911
AllCCS	[M+NH4]+	161.2	32859911
AllCCS	[M+Na]+	162.1	32859911
AllCCS	[M-H]-	160.5	32859911
AllCCS	[M+Na-2H]-	160.5	32859911
AllCCS	[M+HCOO]-	160.6	32859911

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.	2.78 minutes	32390414
Predicted by Siyang on May 30, 2022	9.6931 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.47 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1360.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	223.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	103.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	153.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	59.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	249.3 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	320.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	71.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	672.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	333.3 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	990.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	217.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	215.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	443.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	163.5 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	128.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-(3-Carboxypropyl)-3,7-dimethylxanthine	CN1C=NC2=C1C(=O)N(CCCC(O)=O)C(=O)N2C	3060.6	Standard polar	33892256
1-(3-Carboxypropyl)-3,7-dimethylxanthine	CN1C=NC2=C1C(=O)N(CCCC(O)=O)C(=O)N2C	1189.8	Standard non polar	33892256
1-(3-Carboxypropyl)-3,7-dimethylxanthine	CN1C=NC2=C1C(=O)N(CCCC(O)=O)C(=O)N2C	2448.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0690000000-248c7f8deca5f24cf2b6	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 40V, Positive-QTOF	splash10-0006-0920000000-c618ab20f3d533acb3f7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 40V, Positive-QTOF	splash10-0006-0920000000-bdf47319ce80ec973faf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 30V, Positive-QTOF	splash10-0006-0960000000-60d44391f4604aa82905	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 10V, Positive-QTOF	splash10-0002-0090000000-9120bde9ab1782f488a8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 20V, Positive-QTOF	splash10-00di-0190000000-c88e9b208734bcf59f2f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 50V, Positive-QTOF	splash10-02g6-0900000000-e165757f06530db71044	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 50V, Positive-QTOF	splash10-02g6-0900000000-b56091a53ea9796f0de4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 35V, Positive-QTOF	splash10-00dm-0490000000-6ae793d906c532d3d6d3	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 10V, Positive-QTOF	splash10-0002-0090000000-3a5d647b87a8df8d4b4b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 20V, Positive-QTOF	splash10-05ub-0590000000-bfaad2a388f3cec67e2f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 40V, Positive-QTOF	splash10-000x-9400000000-c50f04da35e0f802fb98	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 10V, Negative-QTOF	splash10-014i-0290000000-0f504c7afd047545afb8	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 20V, Negative-QTOF	splash10-05ot-0590000000-28e24e472dec37a1f0fc	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 40V, Negative-QTOF	splash10-0k96-9700000000-9bf76d1f051f951d86e6	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 10V, Positive-QTOF	splash10-014i-0090000000-c0ed7d546ddda126e077	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 20V, Positive-QTOF	splash10-00ls-0940000000-d8482d3d04f44f0ca83c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 40V, Positive-QTOF	splash10-03di-2900000000-9e0e9f106e8cafb773e4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 10V, Negative-QTOF	splash10-014i-0290000000-65d1fdfb17968cbec4b2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 20V, Negative-QTOF	splash10-004i-1920000000-0ba6df5f635310de7e5b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(3-Carboxypropyl)-3,7-dimethylxanthine 40V, Negative-QTOF	splash10-0a6r-2910000000-1a0d499ef9729f2bc41f	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

133451

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

151419

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-(3-Carboxypropyl)-3,7-dimethylxanthine (HMDB0243498)

MOL for HMDB0243498 (1-(3-Carboxypropyl)-3,7-dimethylxanthine)

3D MOL for HMDB0243498 (1-(3-Carboxypropyl)-3,7-dimethylxanthine)

3D SDF for HMDB0243498 (1-(3-Carboxypropyl)-3,7-dimethylxanthine)

3D-SDF for HMDB0243498 (1-(3-Carboxypropyl)-3,7-dimethylxanthine)

PDB for HMDB0243498 (1-(3-Carboxypropyl)-3,7-dimethylxanthine)

3D PDB for HMDB0243498 (1-(3-Carboxypropyl)-3,7-dimethylxanthine)

SMILES for HMDB0243498 (1-(3-Carboxypropyl)-3,7-dimethylxanthine)

INCHI for HMDB0243498 (1-(3-Carboxypropyl)-3,7-dimethylxanthine)

Structure for HMDB0243498 (1-(3-Carboxypropyl)-3,7-dimethylxanthine)

3D Structure for HMDB0243498 (1-(3-Carboxypropyl)-3,7-dimethylxanthine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra