Showing NP-Card for Theophylline (NP0000929)

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Record Information
Version2.0
Created at2006-02-28 12:15:37 UTC
Updated at2025-02-11 15:45:43 UTC
NP-MRD IDNP0000929
Natural Product DOIhttps://doi.org/10.57994/0496
Secondary Accession NumbersNone
Natural Product Identification
Common NameTheophylline
DescriptionTheophylline, also known as quibron TSR or uniphyl, 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. Theophylline also binds to the adenosine A2B receptor and blocks adenosine mediated bronchoconstriction. Theophylline is a drug which is used for the treatment of the symptoms and reversible airflow obstruction associated with chronic asthma and other chronic lung diseases, such as emphysema and chronic bronchitis. Theophylline is marketed under several brand names such as Theophylline and Theochron, and it is indicated mainly for asthma, bronchospasm, and COPD. Within humans, theophylline participates in a number of enzymatic reactions. In particular, theophylline and formaldehyde can be biosynthesized from caffeine; which is mediated by the enzymes cytochrome P450 1A2, cytochrome P450 3A4, cytochrome P450 2C8, cytochrome P450 2C9, and cytochrome P450 2E1. In addition, theophylline can be converted into 1-methylxanthine and formaldehyde; which is mediated by the enzyme cytochrome P450 1A2. In humans, theophylline is involved in caffeine metabolism. Theophylline is a bitter tasting compound. Outside of the human body, Theophylline is found, on average, in the highest concentration within cocoa beans and tea. Theophylline has also been detected, but not quantified in a few different foods, such as arabica coffee, lemons, and pummelo. This could make theophylline a potential biomarker for the consumption of these foods. Theophylline is a potentially toxic compound.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000929 (Theophylline)

  Mrv1652305271900302D          

 13 14  0  0  0  0            999 V2000
    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
   -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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  2  0  0  0  0
  7 10  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  3 13  1  0  0  0  0
M  END
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3D MOL for NP0000929 (Theophylline)

HMDB0001889
     RDKit          3D
Theophylline
 21 22  0  0  0  0  0  0  0  0999 V2000
    2.9395   -0.3331    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5057   -0.1723    0.0590 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7601   -1.2413   -0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2833   -2.3464   -0.5167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6301   -1.1600   -0.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6109   -2.0398   -0.6296 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7755   -1.3738   -0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5070   -0.1024   -0.1891 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1857    0.0707   -0.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3901    1.1261    0.2682 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0401    2.3789    0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9573    1.0220    0.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6762    2.0228    0.6367 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1908   -0.6738    1.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4741    0.6160   -0.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2847   -1.0761   -0.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285   -3.0354   -0.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7625   -1.8225   -0.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4018    3.0674    1.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3395    2.8443   -0.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9996    2.2286    1.1036 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  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12  2  1  0
  9  5  2  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  6 17  1  0
  7 18  1  0
 11 19  1  0
 11 20  1  0
 11 21  1  0
M  END
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3D SDF for NP0000929 (Theophylline)

  Mrv1652305271900302D          

 13 14  0  0  0  0            999 V2000
    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
   -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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  2  0  0  0  0
  7 10  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  3 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000929

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)

> <INCHI_KEY>
ZFXYFBGIUFBOJW-UHFFFAOYSA-N

> <FORMULA>
C7H8N4O2

> <MOLECULAR_WEIGHT>
180.164

> <EXACT_MASS>
180.06472552

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.855400878563223

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.26

> <JCHEM_LOGP>
-0.7693216573333334

> <ALOGPS_LOGS>
-0.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.815127426971925

> <JCHEM_PKA_STRONGEST_BASIC>
-0.77711753278622

> <JCHEM_POLAR_SURFACE_AREA>
69.30000000000001

> <JCHEM_REFRACTIVITY>
44.9345

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.29e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
theophylline

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0000929 (Theophylline)

HMDB0001889
     RDKit          3D
Theophylline
 21 22  0  0  0  0  0  0  0  0999 V2000
    2.9395   -0.3331    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5057   -0.1723    0.0590 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7601   -1.2413   -0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2833   -2.3464   -0.5167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6301   -1.1600   -0.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6109   -2.0398   -0.6296 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7755   -1.3738   -0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5070   -0.1024   -0.1891 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1857    0.0707   -0.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3901    1.1261    0.2682 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0401    2.3789    0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9573    1.0220    0.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6762    2.0228    0.6367 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1908   -0.6738    1.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4741    0.6160   -0.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2847   -1.0761   -0.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285   -3.0354   -0.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7625   -1.8225   -0.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4018    3.0674    1.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3395    2.8443   -0.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9996    2.2286    1.1036 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  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12  2  1  0
  9  5  2  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  6 17  1  0
  7 18  1  0
 11 19  1  0
 11 20  1  0
 11 21  1  0
M  END
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PDB for NP0000929 (Theophylline)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -1.465   2.016   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -2.370   0.770   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -1.465  -0.476   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   10                                                  
CONECT    8    7    2    9                                                  
CONECT    9    8                                                            
CONECT   10    7                                                            
CONECT   11    4   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    3                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for NP0000929 (Theophylline)

COMPND    HMDB0001889
HETATM    1  C1  UNL     1       2.939  -0.333   0.113  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.506  -0.172   0.059  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.760  -1.241  -0.266  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.283  -2.346  -0.517  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.630  -1.160  -0.338  1.00  0.00           C  
HETATM    6  N2  UNL     1      -1.611  -2.040  -0.630  1.00  0.00           N  
HETATM    7  C4  UNL     1      -2.776  -1.374  -0.535  1.00  0.00           C  
HETATM    8  N3  UNL     1      -2.507  -0.102  -0.189  1.00  0.00           N  
HETATM    9  C5  UNL     1      -1.186   0.071  -0.057  1.00  0.00           C  
HETATM   10  N4  UNL     1      -0.390   1.126   0.268  1.00  0.00           N  
HETATM   11  C6  UNL     1      -1.040   2.379   0.548  1.00  0.00           C  
HETATM   12  C7  UNL     1       0.957   1.022   0.331  1.00  0.00           C  
HETATM   13  O2  UNL     1       1.676   2.023   0.637  1.00  0.00           O  
HETATM   14  H1  UNL     1       3.191  -0.674   1.139  1.00  0.00           H  
HETATM   15  H2  UNL     1       3.474   0.616  -0.145  1.00  0.00           H  
HETATM   16  H3  UNL     1       3.285  -1.076  -0.648  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.429  -3.035  -0.874  1.00  0.00           H  
HETATM   18  H5  UNL     1      -3.762  -1.823  -0.716  1.00  0.00           H  
HETATM   19  H6  UNL     1      -0.402   3.067   1.139  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.339   2.844  -0.423  1.00  0.00           H  
HETATM   21  H8  UNL     1      -2.000   2.229   1.104  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   12
CONECT    3    4    4    5
CONECT    5    6    9    9
CONECT    6    7   17
CONECT    7    8    8   18
CONECT    8    9
CONECT    9   10
CONECT   10   11   12
CONECT   11   19   20   21
CONECT   12   13   13
END
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SMILES for NP0000929 (Theophylline)

CN1C2=C(NC=N2)C(=O)N(C)C1=O
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INCHI for NP0000929 (Theophylline)

InChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)
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Synonyms
Chemical FormulaC7H8N4O2
Average Mass180.1640 Da
Monoisotopic Mass180.06473 Da
IUPAC Name1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Nametheophylline
CAS Registry Number58-55-9
SMILES
CN1C2=C(NC=N2)C(=O)N(C)C1=O
InChI Identifier
InChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)
InChI KeyZFXYFBGIUFBOJW-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HMBC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)john.cort@pnnl.govNot AvailableNot Available2024-05-11View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)john.cort@pnnl.govNot AvailableNot Available2024-05-11View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)john.cort@pnnl.govNot AvailableNot Available2024-05-11View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, CDCL3, experimental)john.cort@pnnl.govNot AvailableNot Available2024-05-11View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCL3, experimental)john.cort@pnnl.govNot AvailableNot Available2024-05-11View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500.11, CDCl3, simulated)john.cort@pnnl.govNot AvailableNot Available2024-05-11View Spectrum
Species
Species of Origin
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point273 °CNot Available
Boiling Point196.00 to 197.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility7.36 mg/mL at 25 °CNot Available
LogP-0.02Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility22.9 g/LALOGPS
logP-0.26ALOGPS
logP-0.77ChemAxon
logS-0.9ALOGPS
pKa (Strongest Acidic)7.82ChemAxon
pKa (Strongest Basic)-0.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.93 m³·mol⁻¹ChemAxon
Polarizability16.86 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001889
DrugBank IDDB00277
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000453
KNApSAcK IDC00001510
Chemspider ID2068
KEGG Compound IDC07130
BioCyc IDCPD-12479
BiGG IDNot Available
Wikipedia LinkTheophylline
METLIN ID1458
PubChem Compound2153
PDB IDNot Available
ChEBI ID28177
Good Scents IDrw1548121
References
General References