Showing metabocard for Theophylline (MMDBc0053805)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-05-16 21:35:20 UTC
Update Date2024-04-30 20:50:24 UTC
Metabolite IDMMDBc0053805
Metabolite 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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x000055e8c8cf40c0>


  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 #<Metabolite:0x000055e8c8cf40c0>

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 #<Metabolite:0x000055e8c8cf40c0>


  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>
MMDBc0053805

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x000055e8c8cf40c0>

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 #<Metabolite:0x000055e8c8cf40c0>

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 #<Metabolite:0x000055e8c8cf40c0>

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 #<Metabolite:0x000055e8c8cf40c0>

CN1C2=C(NC=N2)C(=O)N(C)C1=O
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INCHI for #<Metabolite:0x000055e8c8cf40c0>

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
ValueSource
1,3-Dimethyl-7H-purine-2,6-dioneChEBI
1,3-DimethylxanthineChEBI
ElixophyllinChEBI
RespbidChEBI
Theo-durChEBI
TheolairChEBI
TheophyllinChEBI
Theophylline anhydrousChEBI
UniphylChEBI
Quibron-tKegg
Theo-24Kegg
Theodur gKegg
AccurbronHMDB
Acet-theocinHMDB
AerolateHMDB
Aerolate IIIHMDB
Aerolate SRHMDB
AminophyllineHMDB
AquaphyllinHMDB
ArmophyllineHMDB
AsbronHMDB
AsmaxHMDB
AustynHMDB
BronkodylHMDB
Bronkodyl SRHMDB
Choledyl saHMDB
Constant-THMDB
DiphyllinHMDB
DoraphyllinHMDB
DuraphylHMDB
Dyspne-inhalHMDB
ElixexHMDB
ElixiconHMDB
ElixominHMDB
Elixophyllin SRHMDB
ElixophyllineHMDB
EuphyllineHMDB
EuphylongHMDB
LabidHMDB
LanophyllinHMDB
LiquophyllineHMDB
LiquoriceHMDB
MaphyllineHMDB
MedaphyllinHMDB
NuelinHMDB
OptiphyllinHMDB
ParkophyllinHMDB
PseudotheophyllineHMDB
Quibron t/srHMDB
Quibron-t/srHMDB
Slo-bidHMDB
Slo-phyllinHMDB
SolosinHMDB
Somophyllin-CRTHMDB
Somophyllin-DFHMDB
Somophyllin-THMDB
Spophyllin retardHMDB
SustaireHMDB
SynophylateHMDB
Synophylate-l.a. cenulesHMDB
T-PhylHMDB
TefaminHMDB
TeofilinaHMDB
TeofyllaminHMDB
TeolairHMDB
TheacitinHMDB
Theal tabl.HMDB
Theal tabletsHMDB
Theo-dur-sprinkleHMDB
TheobidHMDB
Theobid jr.HMDB
TheochronHMDB
TheocinHMDB
Theoclair-SRHMDB
Theoclear 80HMDB
Theoclear l.a.-130HMDB
Theoclear laHMDB
Theoclear-200HMDB
Theoclear-80HMDB
TheocontinHMDB
TheodelHMDB
TheofolHMDB
TheogradHMDB
Theolair-SRHMDB
TheolixHMDB
TheolixirHMDB
Theona pHMDB
TheophylHMDB
Theophyl-225HMDB
Theophyl-SRHMDB
TheophylineHMDB
Theophylline-SRHMDB
Theostat 80HMDB
TheoventHMDB
Uni-durHMDB
UnifylHMDB
UniphyllinHMDB
XanthiumHMDB
XantiventHMDB
AerobinHMDB
BronchoparatHMDB
Glycine theophyllinateHMDB
Nuelin s.a.HMDB
Slo phyllinHMDB
SloPhyllinHMDB
Somophyllin THMDB
Theo24HMDB
Theoconfin continuousHMDB
TheoniteHMDB
CT Arzneimittel brand OF theophylline sodium glycinateHMDB
Von CT, theoHMDB
Mundipharma brand OF theophylline sodium glycinateHMDB
Quibron T SRHMDB
Quibron T-SRHMDB
Sodium glycinate, theophyllineHMDB
Theo 24HMDB
Theophyllinate, glycineHMDB
Theophylline sodium glycinateHMDB
TheospanHMDB
UniphyllineHMDB
CT-Arzneimittel brand OF theophylline sodium glycinateHMDB
ConstantTHMDB
Fameasan brand OF theophylline sodium glycinateHMDB
LodraneHMDB
MonospanHMDB
Quibron TSRHMDB
TheodurHMDB
TheonHMDB
TheopekHMDB
TheostatHMDB
CT, Theo vonHMDB
Theo von CTHMDB
1,3 DimethylxanthineHMDB
3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dioneHMDB
Afonilum retardHMDB
Anhydrous, theophyllineHMDB
Constant THMDB
Fujisawa brand OF theophylline sodium glycinateHMDB
Glycinate, theophylline sodiumHMDB
SomophyllinTHMDB
Theo durHMDB
Molecular FormulaC7H8N4O2
Average Mass180.164
Monoisotopic Mass180.06472552
IUPAC Name1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Nametheophylline
CAS Registry NumberNot Available
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