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Showing metabocard for Caffeine (HMDB0001847)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (30)transporters (1) Show 31 proteinsXML
enzymes (30)transporters (1) Show 31 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-16 08:53:46 UTC
Update Date2023-02-21 17:15:49 UTC
HMDB IDHMDB0001847
Secondary Accession Numbers
  • HMDB01847
Metabolite Identification
Common NameCaffeine
DescriptionCaffeine is a methyl xanthine alkaloid that is also classified as a purine. Formally, caffeine 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. Caffeine is chemically related to the adenine and guanine bases of deoxyribonucleic acid (DNA) and ribonucleic acid (RNA). It is found in the seeds, nuts, or leaves of a number of plants native to Africa, East Asia and South America and helps to protect them against predator insects and to prevent germination of nearby seeds. The most well-known source of caffeine is the coffee bean. Caffeine is the most widely consumed psychostimulant drug in the world. 85% of American adults consumed some form of caffeine daily, consuming 164 mg on average. Caffeine is mostly is consumed in the form of coffee. Caffeine is a central nervous system stimulant that reduces fatigue and drowsiness. At normal doses, caffeine has variable effects on learning and memory, but it generally improves reaction time, wakefulness, concentration, and motor coordination. Caffeine is a proven ergogenic aid in humans. Caffeine improves athletic performance in aerobic (especially endurance sports) and anaerobic conditions. Moderate doses of caffeine (around 5 mg/kg) can improve sprint performance, cycling and running time trial performance, endurance and cycling power output (PMID: 32551869 ). At intake levels associated with coffee consumption, caffeine appears to exert most of its biological effects through the antagonism of the A1 and A2A subtypes of the adenosine receptor. Adenosine is an endogenous neuromodulator with mostly inhibitory effects, and adenosine antagonism by caffeine results in effects that are generally stimulatory. Some physiological effects associated with caffeine administration include central nervous system stimulation, acute elevation of blood pressure, increased metabolic rate, and diuresis. A number of in vitro and in vivo studies have demonstrated that caffeine modulates both innate and adaptive immune responses. For instance, studies indicate that caffeine and its major metabolite paraxanthine suppress neutrophil and monocyte chemotaxis, and also suppress production of the pro-inflammatory cytokine tumor necrosis factor (TNF) alpha from human blood. Caffeine has also been reported to suppress human lymphocyte function as indicated by reduced T-cell proliferation and impaired production of Th1 (interleukin [IL]-2 and interferon [IFN]-gamma), Th2 (IL-4, IL-5) and Th3 (IL-10) cytokines. Studies also indicate that caffeine suppresses antibody production. The evidence suggests that at least some of the immunomodulatory actions of caffeine are mediated via inhibition of cyclic adenosine monophosphate (cAMP)-phosphodiesterase (PDE), and consequential increase in intracellular cAMP concentrations. Overall, these studies indicate that caffeine, like other members of the methylxanthine family, is largely anti-inflammatory in nature, and based on the pharmacokinetics of caffeine, many of its immunomodulatory effects occur at concentrations that are relevant to normal human consumption. (PMID: 16540173 ). Caffeine is rapidly and almost completely absorbed in the stomach and small intestine and distributed to all tissues, including the brain. Caffeine metabolism occurs primarily in the liver, where the activity of the cytochrome P450 isoform CYP1A2 accounts for almost 95% of the primary metabolism of caffeine. CYP1A2-catalyzed 3-demethylation of caffeine results in the formation of 1,7-dimethylxanthine (paraxanthine). Paraxanthine may be demethylated by CYP1A2 to form 1-methylxanthine, which may be oxidized to 1-methyluric acid by xanthine oxidase. Paraxanthine may also be hydroxylated by CYP2A6 to form 1,7-dimethyluric acid, or acetylated by N-acetyltransferase 2 (NAT2) to form 5-acetylamino-6-formylamino-3-methyluracil, an unstable compound that may be deformylated nonenzymatically to form 5-acetylamino-6-amino-3-methyluracil. Caffeine concentrations in coffee beverages can be quite variable. A standard cup of coffee is often assumed to provide 100 mg of caffeine, but a recent analysis of 14 different specialty coffees purchased at coffee shops in the US found that the amount of caffeine in 8 oz (=240 ml) of brewed coffee ranged from 72 to 130 mg. Caffeine in espresso coffees ranged from 58 to 76 mg in a single shot. (PMID: 16507475 ).
Structure
Data?1676999749
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001847 (Caffeine)

201
  Mrv1652305201900032D          

 14 15  0  0  0  0            999 V2000
    3.0791    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741    0.6639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -0.6639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0556    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8305    1.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
  2 10  2  0  0  0  0
  3  8  1  0  0  0  0
  3 10  1  0  0  0  0
  3 12  1  0  0  0  0
  4  7  1  0  0  0  0
  4 11  1  0  0  0  0
  4 13  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 14  1  0  0  0  0
  6  8  1  0  0  0  0
  6 11  2  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
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3D MOL for HMDB0001847 (Caffeine)

HMDB0001847
     RDKit          3D
Caffeine
 24 25  0  0  0  0  0  0  0  0999 V2000
   -2.4636   -2.0174   -0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4669   -0.9535   -0.0773 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1487   -1.2106   -0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2443   -2.3903   -0.1576 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8074   -0.2221   -0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    1.0812    0.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4314    1.8627    0.1211 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5405    1.0949    0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1493   -0.1805   -0.0043 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0454   -1.3035   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9659    1.3673    0.0738 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4311    2.7381    0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8359    0.3377    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0677    0.6243    0.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4593   -1.5791   -0.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2666   -2.6697    0.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3368   -2.6503   -1.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5563    1.4588    0.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5492   -1.4664    0.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8757   -1.0117   -0.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981   -2.2202   -0.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1139    2.8541    1.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927    3.4191    0.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0042    3.0373   -0.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13  2  1  0
  9  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  8 18  1  0
 10 19  1  0
 10 20  1  0
 10 21  1  0
 12 22  1  0
 12 23  1  0
 12 24  1  0
M  END
Download

3D SDF for HMDB0001847 (Caffeine)

201
  Mrv1652305201900032D          

 14 15  0  0  0  0            999 V2000
    3.0791    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741    0.6639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -0.6639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0556    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8305    1.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
  2 10  2  0  0  0  0
  3  8  1  0  0  0  0
  3 10  1  0  0  0  0
  3 12  1  0  0  0  0
  4  7  1  0  0  0  0
  4 11  1  0  0  0  0
  4 13  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 14  1  0  0  0  0
  6  8  1  0  0  0  0
  6 11  2  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001847

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C=NC2=C1C(=O)N(C)C(=O)N2C

> <INCHI_IDENTIFIER>
InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3

> <INCHI_KEY>
RYYVLZVUVIJVGH-UHFFFAOYSA-N

> <FORMULA>
C8H10N4O2

> <MOLECULAR_WEIGHT>
194.1906

> <EXACT_MASS>
194.080375584

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.9549309213843

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.24

> <JCHEM_LOGP>
-0.5456455916666669

> <ALOGPS_LOGS>
-1.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9241843687844741

> <JCHEM_POLAR_SURFACE_AREA>
58.440000000000005

> <JCHEM_REFRACTIVITY>
49.8312

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
caffeine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001847 (Caffeine)

HMDB0001847
     RDKit          3D
Caffeine
 24 25  0  0  0  0  0  0  0  0999 V2000
   -2.4636   -2.0174   -0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4669   -0.9535   -0.0773 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1487   -1.2106   -0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2443   -2.3903   -0.1576 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8074   -0.2221   -0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    1.0812    0.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4314    1.8627    0.1211 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5405    1.0949    0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1493   -0.1805   -0.0043 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0454   -1.3035   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9659    1.3673    0.0738 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4311    2.7381    0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8359    0.3377    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0677    0.6243    0.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4593   -1.5791   -0.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2666   -2.6697    0.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3368   -2.6503   -1.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5563    1.4588    0.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5492   -1.4664    0.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8757   -1.0117   -0.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981   -2.2202   -0.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1139    2.8541    1.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927    3.4191    0.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0042    3.0373   -0.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13  2  1  0
  9  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  8 18  1  0
 10 19  1  0
 10 20  1  0
 10 21  1  0
 12 22  1  0
 12 23  1  0
 12 24  1  0
M  END
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PDB for HMDB0001847 (Caffeine)

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 201                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  O   UNK     0       5.748   3.080   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080  -1.540   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.748  -1.540   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       8.538   1.239   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       4.414   0.770   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       8.538  -1.239   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.081   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.437   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.017   2.703   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   1.540   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3    8   10   12                                                  
CONECT    4    7   11   13                                                  
CONECT    5    9   10   14                                                  
CONECT    6    8   11                                                       
CONECT    7    4    8    9                                                  
CONECT    8    3    6    7                                                  
CONECT    9    1    5    7                                                  
CONECT   10    2    3    5                                                  
CONECT   11    4    6                                                       
CONECT   12    3                                                            
CONECT   13    4                                                            
CONECT   14    5                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END
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3D PDB for HMDB0001847 (Caffeine)

COMPND    HMDB0001847
HETATM    1  C1  UNL     1      -2.464  -2.017  -0.152  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.467  -0.953  -0.077  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.149  -1.211  -0.085  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.244  -2.390  -0.158  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.807  -0.222  -0.016  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.356   1.081   0.064  1.00  0.00           C  
HETATM    7  N2  UNL     1       1.431   1.863   0.121  1.00  0.00           N  
HETATM    8  C5  UNL     1       2.541   1.095   0.079  1.00  0.00           C  
HETATM    9  N3  UNL     1       2.149  -0.181  -0.004  1.00  0.00           N  
HETATM   10  C6  UNL     1       3.045  -1.304  -0.070  1.00  0.00           C  
HETATM   11  N4  UNL     1      -0.966   1.367   0.074  1.00  0.00           N  
HETATM   12  C7  UNL     1      -1.431   2.738   0.158  1.00  0.00           C  
HETATM   13  C8  UNL     1      -1.836   0.338   0.002  1.00  0.00           C  
HETATM   14  O2  UNL     1      -3.068   0.624   0.013  1.00  0.00           O  
HETATM   15  H1  UNL     1      -3.459  -1.579  -0.025  1.00  0.00           H  
HETATM   16  H2  UNL     1      -2.267  -2.670   0.739  1.00  0.00           H  
HETATM   17  H3  UNL     1      -2.337  -2.650  -1.036  1.00  0.00           H  
HETATM   18  H4  UNL     1       3.556   1.459   0.109  1.00  0.00           H  
HETATM   19  H5  UNL     1       3.549  -1.466   0.914  1.00  0.00           H  
HETATM   20  H6  UNL     1       3.876  -1.012  -0.767  1.00  0.00           H  
HETATM   21  H7  UNL     1       2.598  -2.220  -0.452  1.00  0.00           H  
HETATM   22  H8  UNL     1      -2.114   2.854   1.049  1.00  0.00           H  
HETATM   23  H9  UNL     1      -0.593   3.419   0.283  1.00  0.00           H  
HETATM   24  H10 UNL     1      -2.004   3.037  -0.764  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   13
CONECT    3    4    4    5
CONECT    5    6    6    9
CONECT    6    7   11
CONECT    7    8    8
CONECT    8    9   18
CONECT    9   10
CONECT   10   19   20   21
CONECT   11   12   13
CONECT   12   22   23   24
CONECT   13   14   14
END
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SMILES for HMDB0001847 (Caffeine)

CN1C=NC2=C1C(=O)N(C)C(=O)N2C
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INCHI for HMDB0001847 (Caffeine)

InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1,3,7-Trimethyl-2,6-dioxopurineChEBI
1,3,7-Trimethylpurine-2,6-dioneChEBI
1,3,7-TrimethylxanthineChEBI
1-MethyltheobromineChEBI
3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dionChEBI
7-MethyltheophyllineChEBI
Anhydrous caffeineChEBI
CafeinaChEBI
CafeineChEBI
CoffeinChEBI
GuaranineChEBI
KoffeinChEBI
MateinaChEBI
MethyltheobromineChEBI
TeinaChEBI
TheinChEBI
TheineChEBI
RespiaKegg
1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dioneHMDB
1-Methyl-theobromineHMDB
3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dioneHMDB
7-Methyl theophyllineHMDB
Anhydrous caffeine (JP15)HMDB
HycomineHMDB
LanorinalHMDB
MethyltheobromideHMDB
Methylxanthine theophyllineHMDB
Monohydrate caffeineHMDB
PropoxypheneHMDB
Merck dura brand OF caffeineHMDB
Thompson brand 1 OF caffeineHMDB
Bristol-myers squibb brand OF caffeineHMDB
CaffedrineHMDB
DexitacHMDB
Percoffedrinol NHMDB
Pierre fabre brand OF caffeineHMDB
Republic drug brand OF caffeineHMDB
Thompson brand 2 OF caffeineHMDB
VivarinHMDB
Coffeinum NHMDB
Coffeinum purrumHMDB
DurvitanHMDB
GlaxoSmithKline brand OF caffeineHMDB
No dozHMDB
PercutaféineHMDB
Quick-pepHMDB
Seid brand OF caffeineHMDB
Berlin-chemie brand OF caffeineHMDB
Passauer brand OF caffeineHMDB
Quick pepHMDB
QuickPepHMDB
Chemical FormulaC8H10N4O2
Average Molecular Weight194.1906
Monoisotopic Molecular Weight194.080375584
IUPAC Name1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Namecaffeine
CAS Registry Number58-08-2
SMILES
CN1C=NC2=C1C(=O)N(C)C(=O)N2C
InChI Identifier
InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
InChI KeyRYYVLZVUVIJVGH-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
  • Purinone
  • 6-oxopurine
  • Alkaloid or derivatives
  • Pyrimidone
  • Pyrimidine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Imidazole
  • Azole
  • Urea
  • Lactam
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen 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 roleEnvironmental roleIndirect biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point238 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility21.6 mg/mL at 25 °CNot Available
LogP-0.07HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Baker145.430932474
[M+H]+CBM138.330932474
[M+H]+McLean141.2730932474
[M+H]+MetCCS_train_pos140.85430932474
[M+H]+Not Available141.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00000474
Predicted Molecular Properties
PropertyValueSource
Water Solubility11 g/LALOGPS
logP-0.24ALOGPS
logP-0.55ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)-0.92ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area58.44 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity49.83 m³·mol⁻¹ChemAxon
Polarizability18.95 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+143.55831661259
DarkChem[M-H]-140.23931661259
AllCCS[M+H]+141.00732859911
AllCCS[M-H]-141.79532859911
DeepCCS[M+H]+139.96730932474
DeepCCS[M-H]-137.65530932474
DeepCCS[M-2H]-172.44930932474
DeepCCS[M+Na]+146.58230932474
AllCCS[M+H]+141.032859911
AllCCS[M+H-H2O]+136.932859911
AllCCS[M+NH4]+144.932859911
AllCCS[M+Na]+146.032859911
AllCCS[M-H]-141.832859911
AllCCS[M+Na-2H]-142.332859911
AllCCS[M+HCOO]-142.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CaffeineCN1C=NC2=C1C(=O)N(C)C(=O)N2C2136.1Standard polar33892256
CaffeineCN1C=NC2=C1C(=O)N(C)C(=O)N2C1886.9Standard non polar33892256
CaffeineCN1C=NC2=C1C(=O)N(C)C(=O)N2C1812.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Caffeine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (0 TMS)splash10-0536-3900000000-a9e112713ffae6dabdaa2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Caffeine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (0 TMS)splash10-0536-2900000000-8cdcd005b2e7622a02a32014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Caffeine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-052f-0900000000-f1084acfddb2406960732014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Caffeine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-05nf-6900000000-8670a644cee5d9de78d42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Caffeine GC-MS (Non-derivatized)splash10-0536-3900000000-4430852b279a72e348222014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Caffeine EI-B (Non-derivatized)splash10-0006-0900000000-51898e93480e848d7da12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Caffeine CI-B (Non-derivatized)splash10-0002-0900000000-2aed5d425b6a95add5db2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Caffeine EI-B (Non-derivatized)splash10-0a4l-4900000000-3ff72dace6687d242f1f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Caffeine EI-B (Non-derivatized)splash10-0006-1900000000-2ba1fae6e27c7b8369842017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Caffeine CI-B (Non-derivatized)splash10-0002-0900000000-fd859aeb416e320d63792017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Caffeine GC-EI-TOF (Non-derivatized)splash10-0536-3900000000-a9e112713ffae6dabdaa2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Caffeine GC-EI-TOF (Non-derivatized)splash10-0536-2900000000-8cdcd005b2e7622a02a32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Caffeine GC-EI-TOF (Non-derivatized)splash10-052f-0900000000-f1084acfddb2406960732017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Caffeine GC-EI-TOF (Non-derivatized)splash10-05nf-6900000000-8670a644cee5d9de78d42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Caffeine GC-MS (Non-derivatized)splash10-0536-3900000000-4430852b279a72e348222017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Caffeine GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-0900000000-41f36d541d34d20889642017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Caffeine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-052f-8900000000-68b5e9aa3404fb3d8d3a2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0006-0900000000-447fc72b2c709e2e18a92012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-000i-1900000000-5e3b29de16ad91c79fe02012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0006-9100000000-d6f6c52ac36c8f25a5002012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine EI-B (HITACHI M-80) , Positive-QTOFsplash10-0006-0900000000-cddd24399d942b1ac97c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine CI-B (Unknown) , Positive-QTOFsplash10-0002-0900000000-2aed5d425b6a95add5db2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine EI-B (HITACHI M-60) , Positive-QTOFsplash10-0a4l-4900000000-3ff72dace6687d242f1f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine EI-B (HITACHI M-68) , Positive-QTOFsplash10-0006-1900000000-2ba1fae6e27c7b8369842012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine CI-B (HITACHI M-60) , Positive-QTOFsplash10-0002-0900000000-63b9ef42a3e8d59e99972012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-0002-0900000000-185b3d97d8857a0f269d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-0002-0900000000-f8a0c0dd9f5c4a272eaf2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-000i-1900000000-dd8e35226d0704aa657d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-01x9-9800000000-70e3b0eb52481c39d1912012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-001l-9100000000-6d428a5571beb0e3fed42012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0002-0900000000-98bec16f898808c3de682012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive-QTOFsplash10-0002-0900000000-b112e4e059e1ecf98c5f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine DI-ESI-qTof , Positive-QTOFsplash10-00dr-0900000000-42c6f8fc7b924e9c64f32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine LC-ESI-qTof , Positive-QTOFsplash10-000i-4900000000-a60a480f1340558740a22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-695d910d49fc0beb1d542017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine LC-ESI-ITFT , positive-QTOFsplash10-0002-0900000000-094879886a2e72bf0c562017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine LC-ESI-ITFT , positive-QTOFsplash10-0002-0900000000-fa38c865089a3a05f2872017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine LC-ESI-ITFT , positive-QTOFsplash10-000b-0900000000-0e82732a924c974dd0c82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-bfc94c8091471847482b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine LC-ESI-ITFT , positive-QTOFsplash10-000i-1900000000-c8fcf16986c4948982032017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine LC-ESI-ITFT , positive-QTOFsplash10-000i-3900000000-9569e0552abb7ebd145a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Caffeine LC-ESI-ITFT , positive-QTOFsplash10-0002-0900000000-3a924abd44877050c1c92017-09-14HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Epidermis
  • Kidney
  • Liver
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified78.0 (26.0-129.0) uMAdult (>18 years old)BothNormal
    • McPherson, Richar...
    • Louise M. Malark...
 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected and Quantified9.65 +/- 4.82 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.33 (0.0-1.01) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.2 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma 		details
Cerebrospinal Fluid (CSF)Detected and Quantified1.139 +/- 0.407 uMAdult (>18 years old)BothTraumatic Brain Injury (TBI) details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Metastatic melanoma		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal adenoma 		details
UrineDetected and Quantified6.359 +/- 2.152 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified0.5 (0.0-1.35) umol/mmol creatinineAdult (>18 years old)Both
Asthma		 details
Associated Disorders and Diseases
Disease References
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. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. 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 ]
Metastatic melanoma
  1. Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]
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 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB00201
Phenol Explorer Compound IDNot Available
FooDB IDFDB002100
KNApSAcK IDC00001492
Chemspider ID2424
KEGG Compound IDC07481
BioCyc ID1-3-7-TRIMETHYLXANTHINE
BiGG IDNot Available
Wikipedia LinkCaffeine
METLIN ID1455
PubChem Compound2519
PDB IDNot Available
ChEBI ID27732
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000344
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Miyake Y, Sakaguchi K, Iwasaki Y, Ikeda H, Makino Y, Kobashi H, Araki Y, Ando M, Kita K, Shiratori Y: New prognostic scoring model for liver transplantation in patients with non-acetaminophen-related fulminant hepatic failure. Transplantation. 2005 Oct 15;80(7):930-6. [PubMed:16249741 ]
  3. Wilkinson SC, Maas WJ, Nielsen JB, Greaves LC, van de Sandt JJ, Williams FM: Interactions of skin thickness and physicochemical properties of test compounds in percutaneous penetration studies. Int Arch Occup Environ Health. 2006 May;79(5):405-13. Epub 2006 Jan 25. [PubMed:16435152 ]
  4. Spiller HA, Winter ML, Klein-Schwartz W, Bangh SA: Efficacy of activated charcoal administered more than four hours after acetaminophen overdose. J Emerg Med. 2006 Jan;30(1):1-5. [PubMed:16434328 ]
  5. Ayotte P, Dewailly E, Lambert GH, Perkins SL, Poon R, Feeley M, Larochelle C, Pereg D: Biomarker measurements in a coastal fish-eating population environmentally exposed to organochlorines. Environ Health Perspect. 2005 Oct;113(10):1318-24. [PubMed:16203240 ]
  6. Shah S, Budev M, Blazey H, Fairbanks K, Mehta A: Hepatic veno-occlusive disease due to tacrolimus in a single-lung transplant patient. Eur Respir J. 2006 May;27(5):1066-8. [PubMed:16707401 ]
  7. Larson AM, Polson J, Fontana RJ, Davern TJ, Lalani E, Hynan LS, Reisch JS, Schiodt FV, Ostapowicz G, Shakil AO, Lee WM: Acetaminophen-induced acute liver failure: results of a United States multicenter, prospective study. Hepatology. 2005 Dec;42(6):1364-72. [PubMed:16317692 ]
  8. Septer S, Thompson ES, Willemsen-Dunlap A: Anesthesia concerns for children with tuberous sclerosis. AANA J. 2006 Jun;74(3):219-25. [PubMed:16786916 ]
  9. Horrigan LA, Kelly JP, Connor TJ: Immunomodulatory effects of caffeine: friend or foe? Pharmacol Ther. 2006 Sep;111(3):877-92. Epub 2006 Mar 15. [PubMed:16540173 ]
  10. Rodrigues IM, Klein LC: Boiled or filtered coffee? Effects of coffee and caffeine on cholesterol, fibrinogen and C-reactive protein. Toxicol Rev. 2006;25(1):55-69. [PubMed:16856769 ]
  11. Lamarine RJ: Selected health and behavioral effects related to the use of caffeine. J Community Health. 1994 Dec;19(6):449-66. [PubMed:7844249 ]
  12. James JE: Critical review of dietary caffeine and blood pressure: a relationship that should be taken more seriously. Psychosom Med. 2004 Jan-Feb;66(1):63-71. [PubMed:14747639 ]
  13. Higdon JV, Frei B: Coffee and health: a review of recent human research. Crit Rev Food Sci Nutr. 2006;46(2):101-23. [PubMed:16507475 ]
  14. Nehlig A, Daval JL, Debry G: Caffeine and the central nervous system: mechanisms of action, biochemical, metabolic and psychostimulant effects. Brain Res Brain Res Rev. 1992 May-Aug;17(2):139-70. [PubMed:1356551 ]
  15. Benjamin LT Jr, Rogers AM, Rosenbaum A: Coca-Cola, caffeine, and mental deficiency: Harry Hollingworth and the Chattanooga trial of 1911. J Hist Behav Sci. 1991 Jan;27(1):42-55. [PubMed:2010614 ]
  16. Nathanson JA: Caffeine and related methylxanthines: possible naturally occurring pesticides. Science. 1984 Oct 12;226(4671):184-7. [PubMed:6207592 ]
  17. Smit HJ, Gaffan EA, Rogers PJ: Methylxanthines are the psycho-pharmacologically active constituents of chocolate. Psychopharmacology (Berl). 2004 Nov;176(3-4):412-9. Epub 2004 May 5. [PubMed:15549276 ]
  18. Haskell CF, Kennedy DO, Wesnes KA, Milne AL, Scholey AB: A double-blind, placebo-controlled, multi-dose evaluation of the acute behavioural effects of guarana in humans. J Psychopharmacol. 2007 Jan;21(1):65-70. Epub 2006 Mar 13. [PubMed:16533867 ]
  19. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  20. Ferreira TT, da Silva JVF, Bueno NB: Effects of caffeine supplementation on muscle endurance, maximum strength, and perceived exertion in adults submitted to strength training: a systematic review and meta-analyses. Crit Rev Food Sci Nutr. 2021;61(15):2587-2600. doi: 10.1080/10408398.2020.1781051. Epub 2020 Jun 18. [PubMed:32551869 ]

Only showing the first 10 proteins. There are 31 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details
1. 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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Daly JW: Caffeine analogs: biomedical impact. Cell Mol Life Sci. 2007 Aug;64(16):2153-69. [PubMed:17514358 ]
Enzyme Details
2. Cytochrome P450 3A4
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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. 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
3. Cytochrome P450 2C9
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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. 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 2C19
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
Enzyme Details
5. 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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. 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
6. Cytochrome P450 3A43
General function:
Involved in monooxygenase activity
Specific function:
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:
CYP3A43
Uniprot ID:
Q9HB55
Molecular weight:
57756.285
Enzyme Details
7. Cytochrome P450 1B1
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. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular weight:
60845.33
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
8. Cytochrome P450 2D6
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
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
9. Cytochrome P450 2C18
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.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular weight:
55710.075
Enzyme Details
10. Cytochrome P450 2F1
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
May be involved in the metabolism of various pneumotoxicants including naphthalene. Is able to dealkylate ethoxycoumarin, propoxycoumarin, and pentoxyresorufin but possesses no activity toward ethoxyresorufin and only trace dearylation activity toward benzyloxyresorufin. Bioactivates 3-methylindole (3MI) by dehydrogenation to the putative electrophile 3-methylene-indolenine.
Gene Name:
CYP2F1
Uniprot ID:
P24903
Molecular weight:
55500.64

Transporters

Enzyme Details
1. Multidrug resistance protein 1
General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Kim RB, Wandel C, Leake B, Cvetkovic M, Fromm MF, Dempsey PJ, Roden MM, Belas F, Chaudhary AK, Roden DM, Wood AJ, Wilkinson GR: Interrelationship between substrates and inhibitors of human CYP3A and P-glycoprotein. Pharm Res. 1999 Mar;16(3):408-14. [PubMed:10213372 ]
  2. Faassen F, Vogel G, Spanings H, Vromans H: Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. [PubMed:12954186 ]

Only showing the first 10 proteins. There are 31 proteins in total.

Show all enzymes and transporters