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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8) Show 8 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:44 UTC

HMDB ID

HMDB0014789

Secondary Accession Numbers

HMDB14789

Metabolite Identification

Common Name

Dyphylline

Description

Dyphylline is only found in individuals that have used or taken this drug. It is a theophylline derivative with broncho- and vasodilator properties. It is used in the treatment of asthma, cardiac dyspnea, and bronchitis. [PubChem]The bronchodilatory action of dyphylline, as with other xanthines, is thought to be mediated through competitive inhibition of phosphodiesterase with a resulting increase in cyclic AMP producing relaxation of bronchial smooth muscle as well as antagonism of adenosine receptors.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0014789
     RDKit          3D
Dyphylline
 32 33  0  0  0  0  0  0  0  0999 V2000
   -2.9223   -1.9031    1.6184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.3644    0.5200 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2610   -0.3598    0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1132    0.0982    1.9145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4867    0.1968   -0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6320   -0.2915   -1.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2266    0.4162   -2.2852 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8651    1.3069   -1.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4337    1.1765   -0.2343 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8598    1.9392    0.9003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0074    1.3456    1.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3027    2.2135    2.7359 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2788    1.2258    0.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1267    0.3808   -0.2214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5056   -1.2848   -1.7521 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6342   -1.7791   -3.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316   -1.7902   -0.7409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0511   -2.7266   -0.9883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3597   -2.6321    2.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1556   -1.0507    2.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9145   -2.2611    1.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092    2.0132   -1.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0438    2.1168    1.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1881    2.9784    0.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7415    0.3747    2.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3617    1.7151    3.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159    0.8200    1.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6334    2.1965    0.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7166    0.5827   -0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6474   -1.8498   -3.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2950   -1.0552   -3.6672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1576   -2.7485   -3.1220 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  6 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17  2  1  0
  9  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  8 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
M  END

651
  Mrv0541 02231214522D          

 18 19  0  0  1  0            999 V2000
    6.1888    0.2998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.9456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7013    1.8682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6501   -1.5294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5742   -0.0404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.5294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.2919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5742   -1.3683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8305    0.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6378    0.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0557   -0.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8941    1.6981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6501    0.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2 13  2  0  0  0  0
  3 16  1  0  0  0  0
  4 15  2  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 14  1  0  0  0  0
  6 11  1  0  0  0  0
  6 15  1  0  0  0  0
  6 17  1  0  0  0  0
  7 13  1  0  0  0  0
  7 15  1  0  0  0  0
  7 18  1  0  0  0  0
  8 11  1  0  0  0  0
  8 14  2  0  0  0  0
  9 11  2  0  0  0  0
  9 13  1  0  0  0  0
 10 12  1  0  0  0  0
 12 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014789

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2=C(N(CC(O)CO)C=N2)C(=O)N(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14N4O4/c1-12-8-7(9(17)13(2)10(12)18)14(5-11-8)3-6(16)4-15/h5-6,15-16H,3-4H2,1-2H3

> <INCHI_KEY>
KSCFJBIXMNOVSH-UHFFFAOYSA-N

> <FORMULA>
C10H14N4O4

> <MOLECULAR_WEIGHT>
254.2426

> <EXACT_MASS>
254.101504956

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
24.651239767243045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-(2,3-dihydroxypropyl)-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

> <ALOGPS_LOGP>
-0.98

> <JCHEM_LOGP>
-1.8660825456666665

> <ALOGPS_LOGS>
-1.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.629258284029333

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.909130036369692

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9737219913339484

> <JCHEM_POLAR_SURFACE_AREA>
98.89999999999999

> <JCHEM_REFRACTIVITY>
62.086

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dyphylline

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014789
     RDKit          3D
Dyphylline
 32 33  0  0  0  0  0  0  0  0999 V2000
   -2.9223   -1.9031    1.6184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.3644    0.5200 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2610   -0.3598    0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1132    0.0982    1.9145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4867    0.1968   -0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6320   -0.2915   -1.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2266    0.4162   -2.2852 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8651    1.3069   -1.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4337    1.1765   -0.2343 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8598    1.9392    0.9003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0074    1.3456    1.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3027    2.2135    2.7359 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2788    1.2258    0.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1267    0.3808   -0.2214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5056   -1.2848   -1.7521 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6342   -1.7791   -3.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316   -1.7902   -0.7409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0511   -2.7266   -0.9883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3597   -2.6321    2.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1556   -1.0507    2.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9145   -2.2611    1.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092    2.0132   -1.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0438    2.1168    1.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1881    2.9784    0.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7415    0.3747    2.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3617    1.7151    3.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159    0.8200    1.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6334    2.1965    0.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7166    0.5827   -0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6474   -1.8498   -3.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2950   -1.0552   -3.6672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1576   -2.7485   -3.1220 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  6 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17  2  1  0
  9  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  8 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 651                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.552   0.560   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.748   1.765   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.509   3.487   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.080  -2.855   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       8.539  -0.075   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       5.748  -2.855   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       4.414  -0.545   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       8.539  -2.554   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       7.081  -0.545   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.017   1.388   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -2.085   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.524   1.706   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748   0.225   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.437  -1.315   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -2.085   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.002   3.170   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.748  -4.395   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.080   0.225   0.000  0.00  0.00           C+0
CONECT    1   12                                                            
CONECT    2   13                                                            
CONECT    3   16                                                            
CONECT    4   15                                                            
CONECT    5    9   10   14                                                  
CONECT    6   11   15   17                                                  
CONECT    7   13   15   18                                                  
CONECT    8   11   14                                                       
CONECT    9    5   11   13                                                  
CONECT   10    5   12                                                       
CONECT   11    6    8    9                                                  
CONECT   12    1   10   16                                                  
CONECT   13    2    7    9                                                  
CONECT   14    5    8                                                       
CONECT   15    4    6    7                                                  
CONECT   16    3   12                                                       
CONECT   17    6                                                            
CONECT   18    7                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0014789
HETATM    1  C1  UNL     1      -2.922  -1.903   1.618  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.143  -1.364   0.520  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.261  -0.360   0.772  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.113   0.098   1.915  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.487   0.197  -0.240  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.632  -0.292  -1.507  1.00  0.00           C  
HETATM    7  N2  UNL     1       0.227   0.416  -2.285  1.00  0.00           N  
HETATM    8  C5  UNL     1       0.865   1.307  -1.481  1.00  0.00           C  
HETATM    9  N3  UNL     1       0.434   1.177  -0.234  1.00  0.00           N  
HETATM   10  C6  UNL     1       0.860   1.939   0.900  1.00  0.00           C  
HETATM   11  C7  UNL     1       2.007   1.346   1.657  1.00  0.00           C  
HETATM   12  O2  UNL     1       2.303   2.213   2.736  1.00  0.00           O  
HETATM   13  C8  UNL     1       3.279   1.226   0.872  1.00  0.00           C  
HETATM   14  O3  UNL     1       3.127   0.381  -0.221  1.00  0.00           O  
HETATM   15  N4  UNL     1      -1.506  -1.285  -1.752  1.00  0.00           N  
HETATM   16  C9  UNL     1      -1.634  -1.779  -3.110  1.00  0.00           C  
HETATM   17  C10 UNL     1      -2.232  -1.790  -0.741  1.00  0.00           C  
HETATM   18  O4  UNL     1      -3.051  -2.727  -0.988  1.00  0.00           O  
HETATM   19  H1  UNL     1      -2.360  -2.632   2.203  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.156  -1.051   2.320  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.915  -2.261   1.272  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.609   2.013  -1.813  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.044   2.117   1.635  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.188   2.978   0.599  1.00  0.00           H  
HETATM   25  H7  UNL     1       1.741   0.375   2.097  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.362   1.715   3.586  1.00  0.00           H  
HETATM   27  H9  UNL     1       4.116   0.820   1.471  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.633   2.197   0.471  1.00  0.00           H  
HETATM   29  H11 UNL     1       3.717   0.583  -0.965  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.647  -1.850  -3.623  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.295  -1.055  -3.667  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.158  -2.749  -3.122  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   17
CONECT    3    4    4    5
CONECT    5    6    6    9
CONECT    6    7   15
CONECT    7    8    8
CONECT    8    9   22
CONECT    9   10
CONECT   10   11   23   24
CONECT   11   12   13   25
CONECT   12   26
CONECT   13   14   27   28
CONECT   14   29
CONECT   15   16   17
CONECT   16   30   31   32
CONECT   17   18   18
END

HMDB0014789
     RDKit          3D
Dyphylline
 32 33  0  0  0  0  0  0  0  0999 V2000
   -2.9223   -1.9031    1.6184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.3644    0.5200 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2610   -0.3598    0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1132    0.0982    1.9145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4867    0.1968   -0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6320   -0.2915   -1.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2266    0.4162   -2.2852 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8651    1.3069   -1.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4337    1.1765   -0.2343 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8598    1.9392    0.9003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0074    1.3456    1.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3027    2.2135    2.7359 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2788    1.2258    0.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1267    0.3808   -0.2214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5056   -1.2848   -1.7521 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6342   -1.7791   -3.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2316   -1.7902   -0.7409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0511   -2.7266   -0.9883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3597   -2.6321    2.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1556   -1.0507    2.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9145   -2.2611    1.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092    2.0132   -1.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0438    2.1168    1.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1881    2.9784    0.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7415    0.3747    2.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3617    1.7151    3.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159    0.8200    1.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6334    2.1965    0.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7166    0.5827   -0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6474   -1.8498   -3.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2950   -1.0552   -3.6672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1576   -2.7485   -3.1220 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  6 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17  2  1  0
  9  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  8 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+-)-7-(2,3-Dihydroxypropyl)theophylline	ChEBI
(+-)-Diprophylline	ChEBI
(+-)-Dyphylline	ChEBI
(1,2-Dihydroxy-3-propyl)thiophyllin	ChEBI
1,3-Dimethyl-7-(2,3-dihydroxypropyl)xanthine	ChEBI
7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthine	ChEBI
7-(2,3-Dihydroxypropyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione	ChEBI
7-(2,3-Dihydroxypropyl)theophylline	ChEBI
7-(beta,gamma-Dihydroxypropyl)theophylline	ChEBI
Dihydroxypropyl theopylin	ChEBI
Diprofilina	ChEBI
Diprophylline	ChEBI
Diprophyllinum	ChEBI
Lufyllin	Kegg
7-(b,g-Dihydroxypropyl)theophylline	Generator
7-(Β,γ-dihydroxypropyl)theophylline	Generator
Dihydroxypropyl theophylline	HMDB
Diprofillin	HMDB
Diprofilline	HMDB
Diprophyllin	HMDB
Dipropylline	HMDB
DT	HMDB
Neothylline	HMDB
Dihydroxypropyltheophylline	HMDB
Diphylline	HMDB
Savage brand OF dyphylline	HMDB
Wallace brand OF dyphylline	HMDB
Dilin	HMDB
Dilor brand OF dyphylline	HMDB
Hauck brand OF dyphylline	HMDB
Dylix	HMDB
Lunsco brand OF dyphylline	HMDB
Major brand OF dyphylline	HMDB

Chemical Formula

C₁₀H₁₄N₄O₄

Average Molecular Weight

254.2426

Monoisotopic Molecular Weight

254.101504956

IUPAC Name

7-(2,3-dihydroxypropyl)-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

Traditional Name

dyphylline

CAS Registry Number

479-18-5

SMILES

CN1C2=C(N(CC(O)CO)C=N2)C(=O)N(C)C1=O

InChI Identifier

InChI=1S/C10H14N4O4/c1-12-8-7(9(17)13(2)10(12)18)14(5-11-8)3-6(16)4-15/h5-6,15-16H,3-4H2,1-2H3

InChI Key

KSCFJBIXMNOVSH-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
1,2-diol
Lactam
Urea
Secondary alcohol
Azacycle
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxopurine (CHEBI:4728 )
propane-1,2-diols (CHEBI:4728 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014789)
Membrane (HMDB: HMDB0014789)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	161.5 °C	Not Available
Boiling Point	589.60 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	14.3 g/L	Not Available
LogP	-1.9	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	14.3 g/L	ALOGPS
logP	-0.98	ALOGPS
logP	-1.9	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	13.91	ChemAxon
pKa (Strongest Basic)	-0.97	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	98.9 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	62.09 m³·mol⁻¹	ChemAxon
Polarizability	24.65 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
DarkChem	[M+H]+	157.0	31661259
DarkChem	[M-H]-	155.294	31661259
DeepCCS	[M+H]+	156.147	30932474
DeepCCS	[M-H]-	153.752	30932474
DeepCCS	[M-2H]-	187.017	30932474
DeepCCS	[M+Na]+	162.151	30932474
AllCCS	[M+H]+	155.7	32859911
AllCCS	[M+H-H2O]+	152.1	32859911
AllCCS	[M+NH4]+	158.9	32859911
AllCCS	[M+Na]+	159.9	32859911
AllCCS	[M-H]-	157.4	32859911
AllCCS	[M+Na-2H]-	157.4	32859911
AllCCS	[M+HCOO]-	157.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dyphylline	CN1C2=C(N(CC(O)CO)C=N2)C(=O)N(C)C1=O	2897.7	Standard polar	33892256
Dyphylline	CN1C2=C(N(CC(O)CO)C=N2)C(=O)N(C)C1=O	1800.0	Standard non polar	33892256
Dyphylline	CN1C2=C(N(CC(O)CO)C=N2)C(=O)N(C)C1=O	2385.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dyphylline,1TMS,isomer #1	CN1C(=O)C2=C(N=CN2CC(CO)O[Si](C)(C)C)N(C)C1=O	2343.5	Semi standard non polar	33892256
Dyphylline,1TMS,isomer #2	CN1C(=O)C2=C(N=CN2CC(O)CO[Si](C)(C)C)N(C)C1=O	2350.7	Semi standard non polar	33892256
Dyphylline,2TMS,isomer #1	CN1C(=O)C2=C(N=CN2CC(CO[Si](C)(C)C)O[Si](C)(C)C)N(C)C1=O	2324.8	Semi standard non polar	33892256
Dyphylline,1TBDMS,isomer #1	CN1C(=O)C2=C(N=CN2CC(CO)O[Si](C)(C)C(C)(C)C)N(C)C1=O	2589.5	Semi standard non polar	33892256
Dyphylline,1TBDMS,isomer #2	CN1C(=O)C2=C(N=CN2CC(O)CO[Si](C)(C)C(C)(C)C)N(C)C1=O	2595.7	Semi standard non polar	33892256
Dyphylline,2TBDMS,isomer #1	CN1C(=O)C2=C(N=CN2CC(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N(C)C1=O	2799.7	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Membrane

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	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00651	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00651	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00651

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00030143

Chemspider ID

3070

KEGG Compound ID

C07819

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dyphylline

METLIN ID

Not Available

PubChem Compound

3182

PDB ID

Not Available

ChEBI ID

4728

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1213631

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. High affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7A

General function:: Involved in 3',5'-cyclic-AMP phosphodiesterase activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May have a role in muscle signal transduction.
Gene Name:: PDE7A
Uniprot ID:: Q13946
Molecular weight:: 55504.475

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

2. cAMP-specific 3',5'-cyclic phosphodiesterase 4B

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in mediating central nervous system effects of therapeutic agents ranging from antidepressants to antiasthmatic and anti-inflammatory agents.
Gene Name:: PDE4B
Uniprot ID:: Q07343
Molecular weight:: 64351.765

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Iancu L, Shneur A, Cohen H: Trials with xanthine derivatives in systemic treatment of psoriasis. Dermatologica. 1979;159(1):55-61. [PubMed:225216 ]
Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. [PubMed:7925603 ]

Enzyme Details

3. cAMP-specific 3',5'-cyclic phosphodiesterase 7B

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in the control of cAMP-mediated neural activity and cAMP metabolism in the brain.
Gene Name:: PDE7B
Uniprot ID:: Q9NP56
Molecular weight:: 51834.855

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

4. cAMP-specific 3',5'-cyclic phosphodiesterase 4C

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name:: PDE4C
Uniprot ID:: Q08493
Molecular weight:: 79900.795

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Iancu L, Shneur A, Cohen H: Trials with xanthine derivatives in systemic treatment of psoriasis. Dermatologica. 1979;159(1):55-61. [PubMed:225216 ]
Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. [PubMed:7925603 ]

Enzyme Details

5. cAMP-specific 3',5'-cyclic phosphodiesterase 4D

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name:: PDE4D
Uniprot ID:: Q08499
Molecular weight:: 91114.1

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. [PubMed:7925603 ]

Enzyme Details

6. cAMP-specific 3',5'-cyclic phosphodiesterase 4A

General function:: Involved in 3',5'-cyclic-nucleotide phosphodiesterase activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name:: PDE4A
Uniprot ID:: P27815
Molecular weight:: 98142.155

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Iancu L, Shneur A, Cohen H: Trials with xanthine derivatives in systemic treatment of psoriasis. Dermatologica. 1979;159(1):55-61. [PubMed:225216 ]
Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. [PubMed:7925603 ]

Enzyme Details

7. Adenosine receptor A1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: ADORA1
Uniprot ID:: P30542
Molecular weight:: 36511.3

References

Schwabe U, Ukena D, Lohse MJ: Xanthine derivatives as antagonists at A1 and A2 adenosine receptors. Naunyn Schmiedebergs Arch Pharmacol. 1985 Sep;330(3):212-21. [PubMed:2997628 ]

Enzyme Details

8. Adenosine receptor A2a

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
Gene Name:: ADORA2A
Uniprot ID:: P29274
Molecular weight:: 44706.9

References

Schwabe U, Ukena D, Lohse MJ: Xanthine derivatives as antagonists at A1 and A2 adenosine receptors. Naunyn Schmiedebergs Arch Pharmacol. 1985 Sep;330(3):212-21. [PubMed:2997628 ]

Showing metabocard for Dyphylline (HMDB0014789)

MOL for HMDB0014789 (Dyphylline)

3D MOL for HMDB0014789 (Dyphylline)

3D SDF for HMDB0014789 (Dyphylline)

3D-SDF for HMDB0014789 (Dyphylline)

PDB for HMDB0014789 (Dyphylline)

3D PDB for HMDB0014789 (Dyphylline)

SMILES for HMDB0014789 (Dyphylline)

INCHI for HMDB0014789 (Dyphylline)

Structure for HMDB0014789 (Dyphylline)

3D Structure for HMDB0014789 (Dyphylline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

References

References

References

References

References

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References