Showing metabocard for Theobromine (MMDBc0053804)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-05-16 21:35:18 UTC
Update Date2024-09-29 09:24:38 UTC
Metabolite IDMMDBc0053804
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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f46ae857518>


  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
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3D MOL for #<Metabolite:0x00007f46ae857518>

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 #<Metabolite:0x00007f46ae857518>


  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>
MMDBc0053804

> <DATABASE_NAME>
MIME

> <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

$$$$
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3D-SDF for #<Metabolite:0x00007f46ae857518>

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
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PDB for #<Metabolite:0x00007f46ae857518>

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 #<Metabolite:0x00007f46ae857518>

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 #<Metabolite:0x00007f46ae857518>

CN1C=NC2=C1C(O)=NC(=O)N2C
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INCHI for #<Metabolite:0x00007f46ae857518>

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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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
Molecular FormulaC7H8N4O2
Average Mass180.164
Monoisotopic Mass180.06472552
IUPAC Name3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Nametheobromine
CAS Registry NumberNot Available
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