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Showing NP-Card for Theobromine (NP0001065)

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Record Information
Version2.0
Created at2006-05-22 15:12:12 UTC
Updated at2024-09-03 04:16:54 UTC
NP-MRD IDNP0001065
Natural Product DOIhttps://doi.org/10.57994/0850
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001065 (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 NP0001065 (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 NP0001065 (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>
NP0001065

> <DATABASE_NAME>
NP-MRD

> <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 NP0001065 (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 NP0001065 (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
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3D PDB for NP0001065 (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
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SMILES for NP0001065 (Theobromine)

CN1C=NC2=C1C(O)=NC(=O)N2C
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INCHI for NP0001065 (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)
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View in JSmol
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 Mass180.1640 Da
Monoisotopic Mass180.06473 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, simulated)V.dorna832021-08-31View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, simulated)Varshavi.d262021-08-18View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)john.cort@pnnl.govNot AvailableNot Available2023-08-24View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)john.cort@pnnl.govNot AvailableNot Available2023-08-24View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)john.cort@pnnl.govNot AvailableNot Available2023-08-24View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, C2D6OS, experimental)john.cort@pnnl.govNot AvailableNot Available2023-08-24View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, C2D6OS, experimental)john.cort@pnnl.govNot AvailableNot Available2023-08-24View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, 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, 499.83, C2D6OS, simulated)john.cort@pnnl.govNot AvailableNot Available2024-05-14View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Abramis bramaFooDB
AcipenserFooDB
AcipenseridaeFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
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Allium sativumFooDB
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Anethum graveolensFooDB
Angelica keiskeiFooDB
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Anthriscus cerefoliumFooDB
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Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
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Camellia theaKNApSAcK Database
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Capra aegagrus hircusFooDB
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CinnamomumFooDB
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Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus aurantiumLOTUS Database
Citrus latifoliaFooDB
Citrus limonKNApSAcK Database
Citrus maximaKNApSAcK Database
Citrus paradisiKNApSAcK Database
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Clupea harengus harengusFooDB
Cocos nuciferaFooDB
Coffea arabicaLOTUS Database
Coffea arabica L.FooDB
Coffea canephoraKNApSAcK Database
Coffea dewevreiKNApSAcK Database
Coffea eugeniodesKNApSAcK Database
Coffea kianjavatensisKNApSAcK Database
Coffea libericaKNApSAcK Database
Coffea racemosaKNApSAcK Database
Coffea salvatrixKNApSAcK Database
Cola acuminataKNApSAcK Database
Cola nitidaLOTUS Database
Cola sp.KNApSAcK Database
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
CoregonusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crassostrea gigasFooDB
Crassostrea virginicaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
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Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Cyprinus carpioFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
EngraulidaeFooDB
Engraulis encrasicolusFooDB
Equus caballusFooDB
Eragrostis tefFooDB
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Eruca vesicaria subsp. SativaFooDB
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EucheumaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
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Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
GadiformesFooDB
GadusFooDB
Gadus macrocephalusFooDB
Gadus morhuaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
GastropodaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Herreania sp.-
Hibiscus sabbariffaFooDB
HippoglossusFooDB
Hippoglossus hippoglossusFooDB
Hippoglossus stenolepisFooDB
Hippophae rhamnoidesFooDB
Homarus americanusFooDB
Hoplostethus atlanticusFooDB
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Ictalurus punctatusFooDB
Ilex paraguariensisLOTUS Database
Ilex paraguariensis A.St.-Hil.KNApSAcK Database
Ilex peradoKNApSAcK Database
Ilex pseudobuxusLOTUS Database
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
LaminariaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Lolium pratenseLOTUS Database
Luffa aegyptiacaFooDB
LupinusFooDB
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LutjanidaeFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
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Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
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Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Merlangius merlangusFooDB
Mespilus germanicaFooDB
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MorchellaceaeFooDB
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Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Mugil cephalusFooDB
Mus musculusLOTUS Database
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Musa x paradisiacaFooDB
MyricaFooDB
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MytilidaeFooDB
Mytilus edulisFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
NephropidaeFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
Octopus vulgarisFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
Oncorhynchus gorbuschaFooDB
Oncorhynchus ketaFooDB
Oncorhynchus kisutchFooDB
Oncorhynchus mykissFooDB
Oncorhynchus nerkaFooDB
Oncorhynchus tshawytschaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
OsmeridaeFooDB
Osmerus mordaxFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Paullinia cupanaKNApSAcK Database
Paullinia pachycarpaKNApSAcK Database
Paullinia trifoliataKNApSAcK Database
Paullinia yocoKNApSAcK Database
PectinidaeFooDB
Pediomelum esculentumFooDB
PerciformesFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
PleuronectiformesFooDB
Pleurotus ostreatusFooDB
Pollachius pollachiusFooDB
Polygonum alpinumFooDB
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Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Pseudopiptadenia leptostachyaKNApSAcK Database
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
RanidaeFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Reinhardtius hippoglossoidesFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scomberomorus maculatusFooDB
Scorzonera hispanicaFooDB
Scurrula atropurpureaKNApSAcK Database
Scurrura atropurpurea-
SebastesFooDB
Sebastes alutusFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
SoleidaeFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
SpirulinaFooDB
SqualiformesFooDB
Stenodus leucichthysFooDB
Stenotomus chrysopsFooDB
StrombidaeFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
TeuthidaFooDB
ThelespermaFooDB
Theobroma-
Theobroma cacaoKNApSAcK Database
Theobroma grandiflorumKNApSAcK Database
Thunnus albacaresFooDB
Thunnus thynnusFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Trachinotus carolinusFooDB
Trachurus symmetricusFooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Typha angustifoliaFooDB
Undaria pinnatifidaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
Virola surinamensisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Xiphias gladiusFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point357 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.33 mg/mL at 25 °CNot Available
LogP-0.78Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility9.74 g/LALOGPS
logP-0.78ALOGPS
logP-0.77ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.28ChemAxon
pKa (Strongest Basic)-0.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area67.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.93 m³·mol⁻¹ChemAxon
Polarizability16.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002825
DrugBank IDDB01412
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDrw1036961
References
General References
  1. Holstege A, Kurz M, Weinbeck M, Gerok W: Excretion of caffeine and its primary degradation products into bile. J Hepatol. 1993 Jan;17(1):67-73. [PubMed:8445222 ]
  2. Delahunty T, Schoendorfer D: Caffeine demethylation monitoring using a transdermal sweat patch. J Anal Toxicol. 1998 Nov-Dec;22(7):596-600. [PubMed:9847011 ]
  3. Blanchard J, Weber CW, Shearer LE: Methylxanthine levels in breast milk of lactating women of different ethnic and socioeconomic classes. Biopharm Drug Dispos. 1992 Apr;13(3):187-96. [PubMed:1576327 ]
  4. Sachse C, Ruschen S, Dettling M, Schley J, Bauer S, Muller-Oerlinghausen B, Roots I, Brockmoller J: Flavin monooxygenase 3 (FMO3) polymorphism in a white population: allele frequencies, mutation linkage, and functional effects on clozapine and caffeine metabolism. Clin Pharmacol Ther. 1999 Oct;66(4):431-8. [PubMed:10546928 ]
  5. Desiraju RK, Sugita ET, Mayock RL: Determination of theophylline and its metabolites by liquid chromatography. J Chromatogr Sci. 1977 Dec;15(12):563-8. [PubMed:591601 ]
  6. Tarka SM Jr, Arnaud MJ, Dvorchik BH, Vesell ES: Theobromine kinetics and metabolic disposition. Clin Pharmacol Ther. 1983 Oct;34(4):546-55. [PubMed:6617078 ]
  7. Tserng KY, King KC, Takieddine FN: Theophylline metabolism in premature infants. Clin Pharmacol Ther. 1981 May;29(5):594-600. [PubMed:7214789 ]
  8. Gonzalez-Jimenez J, Frutos G, Cayre I: Fluorescence quenching of human serum albumin by xanthines. Biochem Pharmacol. 1992 Aug 18;44(4):824-6. [PubMed:1510729 ]
  9. Sommer KR, Hill RM, Horning MG: Identification and quantification of drugs in human amniotic fluid. Res Commun Chem Pathol Pharmacol. 1975 Nov;12(3):583-95. [PubMed:1197933 ]
  10. Skopinska-Rozewska E, Janik P, Przybyszewska M, Sommer E, Bialas-Chromiec B: Inhibitory effect of theobromine on induction of angiogenesis and VEGF mRNA expression in v-raf transfectants of human urothelial cells HCV-29. Int J Mol Med. 1998 Dec;2(6):649-52. [PubMed:9850731 ]
  11. Resman BH, Blumenthal P, Jusko WJ: Breast milk distribution of theobromine from chocolate. J Pediatr. 1977 Sep;91(3):477-80. [PubMed:894424 ]
  12. Scott NR, Chakraborty J, Marks V: Determination of caffeine, theophylline and theobromine in serum and saliva using high-performance liquid chromatography. Ann Clin Biochem. 1984 Mar;21 ( Pt 2):120-4. [PubMed:6712142 ]
  13. Emara S: Simultaneous determination of caffeine, theophylline and theobromine in human plasma by on-line solid-phase extraction coupled to reversed-phase chromatography. Biomed Chromatogr. 2004 Oct;18(8):479-85. [PubMed:15386526 ]
  14. Gennaro MC, Abrigo C, Biglino P: Quantification of theophylline in human plasma by reversed-phase ion-interaction high-performance liquid chromatography and comparison with the TDx fluorescence polarization immunoassay procedure. Analyst. 1992 Jul;117(7):1071-4. [PubMed:1524227 ]
  15. Slattery ML, West DW: Smoking, alcohol, coffee, tea, caffeine, and theobromine: risk of prostate cancer in Utah (United States). Cancer Causes Control. 1993 Nov;4(6):559-63. [PubMed:8280834 ]
  16. Usmani OS, Belvisi MG, Patel HJ, Crispino N, Birrell MA, Korbonits M, Korbonits D, Barnes PJ: Theobromine inhibits sensory nerve activation and cough. FASEB J. 2005 Feb;19(2):231-3. Epub 2004 Nov 17. [PubMed:15548587 ]