Hmdb loader

Showing metabocard for Theobromine (HMDB0002825)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
enzymes (6) Show 6 proteins
Show more...Show more...Show more...Show more...Show more...Show more...
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:12 UTC
Update Date2023-02-21 17:16:29 UTC
HMDB IDHMDB0002825
Secondary Accession Numbers
  • HMDB02825
Metabolite Identification
Common NameTheobromine
DescriptionTheobromine, or 3,7-Dimethylxanthine, is the principle alkaloid in Theobroma cacao (the cacao bean) and other plants. A xanthine alkaloid that is used as a bronchodilator and as a vasodilator. It has a weaker diuretic activity than theophylline and is also a less powerful stimulant of smooth muscle. It has practically no stimulant effect on the central nervous system. It was formerly used as a diuretic and in the treatment of angina pectoris and hypertension. Theobromine is a bitter alkaloid of the methylxanthine family, which also includes the similar compounds theophylline and caffeine. Despite its name, the compound contains no bromine. Theobromine is derived from Theobroma, the genus of the cacao tree, which is composed of the Greek roots theo ("God") and broma ("food"), meaning "food of the gods". It is the primary alkaloid found in cocoa and chocolate, and is one of the causes for chocolate's mood-elevating effects. The amount found in chocolate is small enough that chocolate can be safely consumed by humans in large quantities, but animals that metabolize theobromine more slowly, such as cats and dogs, can easily consume enough chocolate to cause chocolate poisoning. Theobromine is a stimulant frequently confused with caffeine. Theobromine has very different effects on the human body from caffeine; it is a mild, lasting stimulant with a mood improving effect, whereas caffeine has a strong, immediate effect and increases stress. In medicine, it is used as a diuretic, vasodilator, and myocardial stimulant. There is a possible association between prostate cancer and theobromine. Theobromine is a contributing factor in acid reflux because it relaxes the esophageal sphincter muscle, allowing stomach acid access to the esophagus.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002825 (Theobromine)

  Mrv1652309042000272D          

 13 14  0  0  0  0            999 V2000
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  3  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  1  1  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 11  2  1  0  0  0  0
 11  5  1  0  0  0  0
 11  7  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
M  END
Download

3D MOL for HMDB0002825 (Theobromine)

HMDB0002825
     RDKit          3D
Theobromine
 21 22  0  0  0  0  0  0  0  0999 V2000
   -2.9902    0.1578    0.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6614   -0.4263    0.0589 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3202   -1.7246    0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0145   -1.8597    0.1145 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5590   -0.6316   -0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4928    0.2603   -0.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1962    1.6033   -0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2231    2.5401   -0.2102 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1014    1.9503   -0.2518 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1109    1.0639   -0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3212    1.4076   -0.2933 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8456   -0.2432   -0.0949 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9422   -1.1988   -0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0102    1.1734    0.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7120   -0.4486    0.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3799    0.2563   -0.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0879   -2.5043    0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4449    2.9909    0.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1563   -1.4803    0.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6257   -2.1345   -0.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417   -0.7522   -0.5631 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  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
  6  2  1  0
 12  5  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  8 18  1  0
 13 19  1  0
 13 20  1  0
 13 21  1  0
M  END
Download

3D SDF for HMDB0002825 (Theobromine)

  Mrv1652309042000272D          

 13 14  0  0  0  0            999 V2000
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  3  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  1  1  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 11  2  1  0  0  0  0
 11  5  1  0  0  0  0
 11  7  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002825

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C=NC2=C1C(O)=NC(=O)N2C

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

> <INCHI_KEY>
YAPQBXQYLJRXSA-UHFFFAOYSA-N

> <FORMULA>
C7H8N4O2

> <MOLECULAR_WEIGHT>
180.164

> <EXACT_MASS>
180.06472552

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.84759944556188

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.78

> <JCHEM_LOGP>
-0.7693216573333334

> <ALOGPS_LOGS>
-1.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.28030481882757

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9071824149877291

> <JCHEM_POLAR_SURFACE_AREA>
67.23

> <JCHEM_REFRACTIVITY>
44.9345

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.76e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
theobromine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0002825 (Theobromine)

HMDB0002825
     RDKit          3D
Theobromine
 21 22  0  0  0  0  0  0  0  0999 V2000
   -2.9902    0.1578    0.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6614   -0.4263    0.0589 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3202   -1.7246    0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0145   -1.8597    0.1145 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5590   -0.6316   -0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4928    0.2603   -0.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1962    1.6033   -0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2231    2.5401   -0.2102 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1014    1.9503   -0.2518 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1109    1.0639   -0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3212    1.4076   -0.2933 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8456   -0.2432   -0.0949 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9422   -1.1988   -0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0102    1.1734    0.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7120   -0.4486    0.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3799    0.2563   -0.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0879   -2.5043    0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4449    2.9909    0.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1563   -1.4803    0.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6257   -2.1345   -0.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417   -0.7522   -0.5631 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  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
  6  2  1  0
 12  5  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  8 18  1  0
 13 19  1  0
 13 20  1  0
 13 21  1  0
M  END
Download

PDB for HMDB0002825 (Theobromine)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.530  -4.383   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       3.864  -0.533   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       2.530  -2.843   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       2.530   1.777   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.198  -2.843   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3    8   10                                                       
CONECT    4    5    6   10                                                  
CONECT    5    4    8   11                                                  
CONECT    6    4    9   12                                                  
CONECT    7    9   11   13                                                  
CONECT    8    3    5                                                       
CONECT    9    6    7                                                       
CONECT   10    1    3    4                                                  
CONECT   11    2    5    7                                                  
CONECT   12    6                                                            
CONECT   13    7                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
Download

3D PDB for HMDB0002825 (Theobromine)

COMPND    HMDB0002825
HETATM    1  C1  UNL     1      -2.990   0.158   0.062  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.661  -0.426   0.059  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.320  -1.725   0.156  1.00  0.00           C  
HETATM    4  N2  UNL     1       0.015  -1.860   0.115  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.559  -0.632  -0.011  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.493   0.260  -0.045  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.196   1.603  -0.171  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.223   2.540  -0.210  1.00  0.00           O  
HETATM    9  N3  UNL     1       1.101   1.950  -0.252  1.00  0.00           N  
HETATM   10  C6  UNL     1       2.111   1.064  -0.216  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.321   1.408  -0.293  1.00  0.00           O  
HETATM   12  N4  UNL     1       1.846  -0.243  -0.095  1.00  0.00           N  
HETATM   13  C7  UNL     1       2.942  -1.199  -0.057  1.00  0.00           C  
HETATM   14  H1  UNL     1      -3.010   1.173   0.489  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.712  -0.449   0.648  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.380   0.256  -0.984  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.088  -2.504   0.252  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.445   2.991   0.687  1.00  0.00           H  
HETATM   19  H6  UNL     1       3.156  -1.480   0.996  1.00  0.00           H  
HETATM   20  H7  UNL     1       2.626  -2.135  -0.566  1.00  0.00           H  
HETATM   21  H8  UNL     1       3.842  -0.752  -0.563  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    6
CONECT    3    4    4   17
CONECT    4    5
CONECT    5    6    6   12
CONECT    6    7
CONECT    7    8    9    9
CONECT    8   18
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   19   20   21
END
Download

SMILES for HMDB0002825 (Theobromine)

CN1C=NC2=C1C(O)=NC(=O)N2C
Download

INCHI for HMDB0002825 (Theobromine)

InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13)
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dioneChEBI
3,7-Dimethylpurine-2,6-dioneChEBI
3,7-DimethylxanthineChEBI
TheobrominChEBI
TeobrominHMDB
2,6-Dihydroxy-3,7-dimethyl-purineHMDB
3,7-Dimethyl-xanthineHMDB
DiurobromineHMDB
Chemical FormulaC7H8N4O2
Average Molecular Weight180.164
Monoisotopic Molecular Weight180.06472552
IUPAC Name3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Nametheobromine
CAS Registry Number83-67-0
SMILES
CN1C=NC2=C1C(O)=NC(=O)N2C
InChI Identifier
InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13)
InChI KeyYAPQBXQYLJRXSA-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • N-substituted imidazole
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Health effectOrganoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point357 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.33 mg/mL at 25 °CNot Available
LogP-0.78HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg135.24630932474
[M+H]+Baker134.36730932474
[M-H]-Not Available135.246http://allccs.zhulab.cn/database/detail?ID=AllCCS00000354
[M+H]+Not Available134.367http://allccs.zhulab.cn/database/detail?ID=AllCCS00000354
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Kidney
  • Liver
  • Placenta
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Malaria
  1. Akinyinka OO, Sowunmi A, Honeywell R, Renwick AG: The effects of acute falciparum malaria on the disposition of caffeine and the comparison of saliva and plasma-derived pharmacokinetic parameters in adult Nigerians. Eur J Clin Pharmacol. 2000 May;56(2):159-65. [PubMed:10877011 ]
Head injury
  1. Sachse KT, Jackson EK, Wisniewski SR, Gillespie DG, Puccio AM, Clark RS, Dixon CE, Kochanek PM: Increases in cerebrospinal fluid caffeine concentration are associated with favorable outcome after severe traumatic brain injury in humans. J Cereb Blood Flow Metab. 2008 Feb;28(2):395-401. Epub 2007 Aug 8. [PubMed:17684518 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Asthma
  1. Zydron M, Baranowski J, Baranowska I: Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples. J Sep Sci. 2004 Oct;27(14):1166-72. [PubMed:15537072 ]
Autosomal dominant polycystic kidney disease
  1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Associated OMIM IDs
DrugBank IDDB01412
Phenol Explorer Compound IDNot Available
FooDB IDFDB000455
KNApSAcK IDC00001509
Chemspider ID5236
KEGG Compound IDC07480
BioCyc ID3-7-DIMETHYLXANTHINE
BiGG IDNot Available
Wikipedia LinkTheobromine
METLIN ID1456
PubChem Compound5429
PDB IDNot Available
ChEBI ID28946
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000403
Good Scents IDrw1036961
References
Synthesis ReferenceYoon, Hye-Sung; Hwang, In-Gyun; Bang, Won-Gi. Production of theobromine from caffeine by Pseudomonas sp. Chayon Chawon Nonjip (1995), 35(1), 33-39.
Material Safety Data Sheet (MSDS)Not Available
General References

Enzymes

Enzyme Details
1. Xanthine dehydrogenase/oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular weight:
146422.99
Reactions
Theobromine + Water + Oxygen → 3,7-Dimethyluric acid + Hydrogen peroxidedetails
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
  1. Essayan DM: Cyclic nucleotide phosphodiesterases. J Allergy Clin Immunol. 2001 Nov;108(5):671-80. [PubMed:11692087 ]
  2. Fisone G, Borgkvist A, Usiello A: Caffeine as a psychomotor stimulant: mechanism of action. Cell Mol Life Sci. 2004 Apr;61(7-8):857-72. [PubMed:15095008 ]
  3. Daly JW: Caffeine analogs: biomedical impact. Cell Mol Life Sci. 2007 Aug;64(16):2153-69. [PubMed:17514358 ]
  4. Deree J, Martins JO, Melbostad H, Loomis WH, Coimbra R: Insights into the regulation of TNF-alpha production in human mononuclear cells: the effects of non-specific phosphodiesterase inhibition. Clinics (Sao Paulo). 2008 Jun;63(3):321-8. [PubMed:18568240 ]
Enzyme Details
3. Cytochrome P450 2E1
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
4. Cytochrome P450 1A2
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Gates S, Miners JO: Cytochrome P450 isoform selectivity in human hepatic theobromine metabolism. Br J Clin Pharmacol. 1999 Mar;47(3):299-305. [PubMed:10215755 ]
Enzyme Details
5. 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
  1. Chou CC, Vickroy TW: Antagonism of adenosine receptors by caffeine and caffeine metabolites in equine forebrain tissues. Am J Vet Res. 2003 Feb;64(2):216-24. [PubMed:12602592 ]
  2. Gaytan SP, Saadani-Makki F, Bodineau L, Frugiere A, Larnicol N, Pasaro R: Effect of postnatal exposure to caffeine on the pattern of adenosine A1 receptor distribution in respiration-related nuclei of the rat brainstem. Auton Neurosci. 2006 Jun 30;126-127:339-46. Epub 2006 May 15. [PubMed:16702031 ]
  3. Wang SJ: Caffeine facilitation of glutamate release from rat cerebral cortex nerve terminals (synaptosomes) through activation protein kinase C pathway: an interaction with presynaptic adenosine A1 receptors. Synapse. 2007 Jun;61(6):401-11. [PubMed:17372967 ]
  4. Rieg T, Schnermann J, Vallon V: Adenosine A1 receptors determine effects of caffeine on total fluid intake but not caffeine appetite. Eur J Pharmacol. 2007 Jan 26;555(2-3):174-7. Epub 2006 Oct 25. [PubMed:17126319 ]
  5. Mustafa S, Venkatesh P, Pasha K, Mullangi R, Srinivas NR: Altered intravenous pharmacokinetics of topotecan in rats with acute renal failure (ARF) induced by uranyl nitrate: do adenosine A1 antagonists (selective/non-selective) normalize the altered topotecan kinetics in ARF? Xenobiotica. 2006 Dec;36(12):1239-58. [PubMed:17162470 ]
  6. Listos J, Malec D, Fidecka S: Adenosine receptor antagonists intensify the benzodiazepine withdrawal signs in mice. Pharmacol Rep. 2006 Sep-Oct;58(5):643-51. [PubMed:17085856 ]
  7. Fisone G, Borgkvist A, Usiello A: Caffeine as a psychomotor stimulant: mechanism of action. Cell Mol Life Sci. 2004 Apr;61(7-8):857-72. [PubMed:15095008 ]
  8. Daly JW, Jacobson KA, Ukena D: Adenosine receptors: development of selective agonists and antagonists. Prog Clin Biol Res. 1987;230:41-63. [PubMed:3588607 ]
Enzyme Details
6. 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
  1. Chou CC, Vickroy TW: Antagonism of adenosine receptors by caffeine and caffeine metabolites in equine forebrain tissues. Am J Vet Res. 2003 Feb;64(2):216-24. [PubMed:12602592 ]
  2. Riksen NP, Franke B, van den Broek P, Smits P, Rongen GA: The 1976C>T polymorphism in the adenosine A2A receptor gene does not affect the vasodilator response to adenosine in humans in vivo. Pharmacogenet Genomics. 2007 Jul;17(7):551-4. [PubMed:17558310 ]
  3. Zhao G, Messina E, Xu X, Ochoa M, Sun HL, Leung K, Shryock J, Belardinelli L, Hintze TH: Caffeine attenuates the duration of coronary vasodilation and changes in hemodynamics induced by regadenoson (CVT-3146), a novel adenosine A2A receptor agonist. J Cardiovasc Pharmacol. 2007 Jun;49(6):369-75. [PubMed:17577101 ]
  4. Cornelis MC, El-Sohemy A, Campos H: Genetic polymorphism of the adenosine A2A receptor is associated with habitual caffeine consumption. Am J Clin Nutr. 2007 Jul;86(1):240-4. [PubMed:17616786 ]
  5. Fisone G, Borgkvist A, Usiello A: Caffeine as a psychomotor stimulant: mechanism of action. Cell Mol Life Sci. 2004 Apr;61(7-8):857-72. [PubMed:15095008 ]
  6. Daly JW, Jacobson KA, Ukena D: Adenosine receptors: development of selective agonists and antagonists. Prog Clin Biol Res. 1987;230:41-63. [PubMed:3588607 ]