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Showing NP-Card for Paraxanthine (NP0000047)

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Record Information
Version2.0
Created at2006-02-22 11:10:26 UTC
Updated at2021-06-29 00:47:13 UTC
NP-MRD IDNP0000047
Secondary Accession NumbersNone
Natural Product Identification
Common NameParaxanthine
DescriptionParaxanthine, also known as p-xanthine, 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. Paraxanthine exists in all living organisms, ranging from bacteria to humans. Within humans, paraxanthine participates in a number of enzymatic reactions. In particular, paraxanthine and formaldehyde can be biosynthesized from caffeine; which is catalyzed by the enzyme cytochrome P450 1A2. In addition, paraxanthine and acetyl-CoA can be converted into 5-acetylamino-6-formylamino-3-methyluracil through its interaction with the enzyme arylamine N-acetyltransferase 2. In humans, paraxanthine is involved in caffeine metabolism.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000047 (Paraxanthine)


  Mrv1652309042000252D          

 13 14  0  0  0  0            999 V2000
   12.5271  -15.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3441  -16.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7571  -17.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4875  -16.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4875  -17.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7730  -16.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0586  -17.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2721  -17.9676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7730  -18.1252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2721  -16.6327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0586  -16.8877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7730  -15.6502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3441  -18.1252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2 11  1  0  0  0  0
  3 10  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  2  0  0  0  0
  4 10  1  0  0  0  0
  4  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 12  2  0  0  0  0
  6 11  1  0  0  0  0
  7 11  1  0  0  0  0
  7 13  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
Download

3D MOL for NP0000047 (Paraxanthine)

HMDB0001860
     RDKit          3D
Paraxanthine
 21 22  0  0  0  0  0  0  0  0999 V2000
   -2.7364   -1.4248   -0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7022   -0.4165   -0.1122 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0304    0.8641    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2484    1.1780    0.1665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0871    1.8176    0.3293 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2279    1.5556    0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3628    2.2572    0.4588 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4337    1.4543    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9344    0.2298    0.0789 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393   -0.9610   -0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5919    0.2409    0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3891   -0.7131   -0.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0229   -1.9035   -0.3678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2623   -2.3529   -0.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4640   -1.1161   -1.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2673   -1.5475    0.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3725    2.8180    0.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4915    1.7412    0.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8297   -1.4535    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7316   -0.6494   -0.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2401   -1.6185   -0.8798 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  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12  2  1  0
 11  6  2  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  8 18  1  0
 10 19  1  0
 10 20  1  0
 10 21  1  0
M  END
Download

3D SDF for NP0000047 (Paraxanthine)


  Mrv1652309042000252D          

 13 14  0  0  0  0            999 V2000
   12.5271  -15.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3441  -16.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7571  -17.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4875  -16.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4875  -17.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7730  -16.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0586  -17.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2721  -17.9676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7730  -18.1252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2721  -16.6327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0586  -16.8877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7730  -15.6502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3441  -18.1252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2 11  1  0  0  0  0
  3 10  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  2  0  0  0  0
  4 10  1  0  0  0  0
  4  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 12  2  0  0  0  0
  6 11  1  0  0  0  0
  7 11  1  0  0  0  0
  7 13  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000047

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C=NC2=C1C(=O)N(C)C(=O)N2

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

> <INCHI_KEY>
QUNWUDVFRNGTCO-UHFFFAOYSA-N

> <FORMULA>
C7H8N4O2

> <MOLECULAR_WEIGHT>
180.164

> <EXACT_MASS>
180.06472552

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.865495165097393

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
-0.63

> <JCHEM_LOGP>
0.24028833966666654

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.761286686077602

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8667931938763297

> <JCHEM_POLAR_SURFACE_AREA>
67.23

> <JCHEM_REFRACTIVITY>
46.715300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.13e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
paraxanthine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000047 (Paraxanthine)

HMDB0001860
     RDKit          3D
Paraxanthine
 21 22  0  0  0  0  0  0  0  0999 V2000
   -2.7364   -1.4248   -0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7022   -0.4165   -0.1122 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0304    0.8641    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2484    1.1780    0.1665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0871    1.8176    0.3293 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2279    1.5556    0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3628    2.2572    0.4588 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4337    1.4543    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9344    0.2298    0.0789 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393   -0.9610   -0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5919    0.2409    0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3891   -0.7131   -0.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0229   -1.9035   -0.3678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2623   -2.3529   -0.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4640   -1.1161   -1.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2673   -1.5475    0.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3725    2.8180    0.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4915    1.7412    0.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8297   -1.4535    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7316   -0.6494   -0.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2401   -1.6185   -0.8798 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  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12  2  1  0
 11  6  2  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  8 18  1  0
 10 19  1  0
 10 20  1  0
 10 21  1  0
M  END
Download

PDB for NP0000047 (Paraxanthine)

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      23.384 -29.583   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.442 -30.754   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.813 -32.294   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.443 -31.524   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.443 -33.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.110 -30.754   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.776 -33.064   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      22.908 -33.540   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      20.110 -33.834   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      22.908 -31.048   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      18.776 -31.524   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      20.110 -29.214   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      17.442 -33.834   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   10    8                                                       
CONECT    4    5   10    6                                                  
CONECT    5    4    8    9                                                  
CONECT    6    4   12   11                                                  
CONECT    7   11   13    9                                                  
CONECT    8    3    5                                                       
CONECT    9    5    7                                                       
CONECT   10    1    3    4                                                  
CONECT   11    2    6    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 NP0000047 (Paraxanthine)

COMPND    HMDB0001860
HETATM    1  C1  UNL     1      -2.736  -1.425  -0.325  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.702  -0.416  -0.112  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.030   0.864   0.128  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.248   1.178   0.166  1.00  0.00           O  
HETATM    5  N2  UNL     1      -1.087   1.818   0.329  1.00  0.00           N  
HETATM    6  C3  UNL     1       0.228   1.556   0.303  1.00  0.00           C  
HETATM    7  N3  UNL     1       1.363   2.257   0.459  1.00  0.00           N  
HETATM    8  C4  UNL     1       2.434   1.454   0.324  1.00  0.00           C  
HETATM    9  N4  UNL     1       1.934   0.230   0.079  1.00  0.00           N  
HETATM   10  C5  UNL     1       2.739  -0.961  -0.136  1.00  0.00           C  
HETATM   11  C6  UNL     1       0.592   0.241   0.056  1.00  0.00           C  
HETATM   12  C7  UNL     1      -0.389  -0.713  -0.145  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.023  -1.903  -0.368  1.00  0.00           O  
HETATM   14  H1  UNL     1      -2.262  -2.353  -0.671  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.464  -1.116  -1.081  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.267  -1.547   0.640  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.373   2.818   0.517  1.00  0.00           H  
HETATM   18  H5  UNL     1       3.492   1.741   0.398  1.00  0.00           H  
HETATM   19  H6  UNL     1       2.830  -1.454   0.860  1.00  0.00           H  
HETATM   20  H7  UNL     1       3.732  -0.649  -0.542  1.00  0.00           H  
HETATM   21  H8  UNL     1       2.240  -1.619  -0.880  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   12
CONECT    3    4    4    5
CONECT    5    6   17
CONECT    6    7   11   11
CONECT    7    8    8
CONECT    8    9   18
CONECT    9   10   11
CONECT   10   19   20   21
CONECT   11   12
CONECT   12   13   13
END
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SMILES for NP0000047 (Paraxanthine)

CN1C=NC2=C1C(=O)N(C)C(=O)N2
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INCHI for NP0000047 (Paraxanthine)

InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)
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View in JSmol
Synonyms
ValueSource
3,7-Dihydro-1,7-dimethyl-1H-purine-2,6-dioneChEBI
p-XanthineChEBI
1,7-Dimethyl-xanthineHMDB
1,7-DimethylxanthineHMDB
Chemical FormulaC7H8N4O2
Average Mass180.1640 Da
Monoisotopic Mass180.06473 Da
IUPAC Name1,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Nameparaxanthine
CAS Registry Number611-59-6
SMILES
CN1C=NC2=C1C(=O)N(C)C(O)=N2
InChI Identifier
InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)
InChI KeyQUNWUDVFRNGTCO-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apis ceranaLOTUS Database
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
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Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Camellia assamicaKNApSAcK Database
Camellia kissiKNApSAcK Database
Camellia sinensisKNApSAcK Database
Camellia sinensis var. assamicaPlant
Camellia taliensisKNApSAcK Database
Camellia toliensisKNApSAcK Database
Cammellia assamica var.kucha-
Canarium ovatumFooDB
Cannabis sativaCannabisDB
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Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
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Carthamus tinctoriusFooDB
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Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
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Citrus limonKNApSAcK Database
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Citrus paradisiKNApSAcK Database
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabicaKNApSAcK Database
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Coffea canephoraKNApSAcK Database
Coffea dewevreiKNApSAcK Database
Coffea eugeniodesKNApSAcK Database
Coffea kianjavatensisKNApSAcK Database
Coffea libericaKNApSAcK Database
Coffea racemosaKNApSAcK Database
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Cola sp.KNApSAcK Database
Colocasia esculentaFooDB
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Eruca vesicaria subsp. SativaFooDB
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Herreania sp.-
Hibiscus sabbariffaFooDB
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Ilex paraguariensisKNApSAcK Database
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Origanum majoranaFooDB
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Paullinia cupanaKNApSAcK Database
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Photinia melanocarpaFooDB
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PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
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Pimpinella anisumFooDB
PinusFooDB
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Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
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Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
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Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
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Rheum rhabarbarumFooDB
Ribes aureumFooDB
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Rubus occidentalisFooDB
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RumexFooDB
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Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
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
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Theobroma cacaoKNApSAcK Database
Theobroma grandiflorumKNApSAcK Database
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Typha angustifoliaFooDB
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
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Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
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VitisFooDB
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Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
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
  • Hydroxypyrimidine
  • N-substituted imidazole
  • Pyrimidine
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Lactam
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point351 - 352 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.13 g/LALOGPS
logP-0.63ALOGPS
logP0.24ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)10.76ChemAxon
pKa (Strongest Basic)-0.87ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area67.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.72 m³·mol⁻¹ChemAxon
Polarizability16.87 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001860
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022714
KNApSAcK IDC00039930
Chemspider ID4525
KEGG Compound IDC13747
BioCyc ID1-7-DIMETHYLXANTHINE
BiGG IDNot Available
Wikipedia LinkParaxanthine
METLIN ID1457
PubChem Compound4687
PDB IDNot Available
ChEBI ID25858
Good Scents IDNot Available
References
General References
  1. Christensen M, Andersson K, Dalen P, Mirghani RA, Muirhead GJ, Nordmark A, Tybring G, Wahlberg A, Yasar U, Bertilsson L: The Karolinska cocktail for phenotyping of five human cytochrome P450 enzymes. Clin Pharmacol Ther. 2003 Jun;73(6):517-28. [PubMed:12811361 ]
  2. Fuhr U, Rost KL: Simple and reliable CYP1A2 phenotyping by the paraxanthine/caffeine ratio in plasma and in saliva. Pharmacogenetics. 1994 Jun;4(3):109-16. [PubMed:7920690 ]
  3. Tanaka E: Simultaneous determination of caffeine and its primary demethylated metabolites in human plasma by high-performance liquid chromatography. J Chromatogr. 1992 Mar 27;575(2):311-4. [PubMed:1629311 ]
  4. 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 ]
  5. 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 ]
  6. Granfors MT, Backman JT, Laitila J, Neuvonen PJ: Oral contraceptives containing ethinyl estradiol and gestodene markedly increase plasma concentrations and effects of tizanidine by inhibiting cytochrome P450 1A2. Clin Pharmacol Ther. 2005 Oct;78(4):400-11. [PubMed:16198659 ]
  7. Blanchard J, Weber CW, Shearer LE: HPLC analysis of methylxanthines in human breast milk. J Chromatogr Sci. 1990 Dec;28(12):640-2. [PubMed:2292610 ]
  8. Delahunty T, Schoendorfer D: Caffeine demethylation monitoring using a transdermal sweat patch. J Anal Toxicol. 1998 Nov-Dec;22(7):596-600. [PubMed:9847011 ]
  9. Holland DT, Godfredsen KA, Page T, Connor JD: Simple high-performance liquid chromatography method for the simultaneous determination of serum caffeine and paraxanthine following rapid sample preparation. J Chromatogr B Biomed Sci Appl. 1998 Apr 10;707(1-2):105-10. [PubMed:9613939 ]
  10. Fuhr U, Rost KL, Engelhardt R, Sachs M, Liermann D, Belloc C, Beaune P, Janezic S, Grant D, Meyer UA, Staib AH: Evaluation of caffeine as a test drug for CYP1A2, NAT2 and CYP2E1 phenotyping in man by in vivo versus in vitro correlations. Pharmacogenetics. 1996 Apr;6(2):159-76. [PubMed:9156694 ]
  11. Zaigler M, Rietbrock S, Szymanski J, Dericks-Tan JS, Staib AH, Fuhr U: Variation of CYP1A2-dependent caffeine metabolism during menstrual cycle in healthy women. Int J Clin Pharmacol Ther. 2000 May;38(5):235-44. [PubMed:10839467 ]
  12. 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 ]
  13. Wahllander A, Renner E, Karlaganis G: High-performance liquid chromatographic determination of dimethylxanthine metabolites of caffeine in human plasma. J Chromatogr. 1985 Mar 22;338(2):369-75. [PubMed:3998024 ]
  14. Koch JP, ten Tusscher GW, Koppe JG, Guchelaar HJ: Validation of a high-performance liquid chromatography assay for quantification of caffeine and paraxanthine in human serum in the context of CYP1A2 phenotyping. Biomed Chromatogr. 1999 Jun;13(4):309-14. [PubMed:10416066 ]
  15. 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 ]