Showing NP-Card for Theobromine (NP0001065)

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Record Information
Version2.0
Created at2006-05-22 15:12:12 UTC
Updated at2025-02-11 15:46:45 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
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
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