Np mrd loader

Showing NP-Card for Xanthine (NP0000734)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-02-09 15:59:40 UTC
NP-MRD IDNP0000734
Secondary Accession NumbersNone
Natural Product Identification
Common NameXanthine
DescriptionXanthine, also known as 2,6-dioxopurine, 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. Xanthine is also classified as an oxopurine. An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated. Xanthine exists in all living species, ranging from bacteria to plants to humans. In plants, several stimulants can be derived from xanthine, including caffeine, theophylline, and theobromine. Derivatives of xanthine (known collectively as xanthines) are a group of alkaloids commonly used for their effects as mild stimulants and as bronchodilators, notably in the treatment of asthma or influenza symptoms. Within humans, xanthine participates in a number of enzymatic reactions. In particular, xanthine can be biosynthesized from guanine; which is mediated by the enzyme guanine deaminase. In addition, xanthine and ribose 1-phosphate can be biosynthesized from xanthosine through the action of the enzyme purine nucleoside phosphorylase. In humans and other primates, xanthine can be converted to uric acid by the action of the xanthine oxidase enzyme. People with rare genetic disorders, specifically xanthinuria and Lesch–Nyhan syndrome, lack sufficient xanthine oxidase and cannot convert xanthine to uric acid. Individuals with xanthinuria have unusually high concentrations of xanthine in their blood and urine, which can lead to health problems such as renal failure and xanthine kidney stones. Individuals with Lesch-Nyhan syndrome have a deficiency of the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRT). The HGPRT deficiency causes a build-up of uric acid in all body fluids. This results in both high levels of uric acid in the blood and urine, associated with severe gout and kidney problems. Neurological signs include poor muscle control and moderate intellectual disability.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000734 (Xanthine)

 
  Mrv1652309042000002D          

 11 12  0  0  0  0            999 V2000
   14.2313   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2313  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9738   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4888   -9.2400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9738  -10.7250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4888  -10.5600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6750   -9.4875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9738   -8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9938   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6750  -10.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4175  -10.6837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6  9  2  0  0  0  0
  7 10  1  0  0  0  0
M  END
Download

3D MOL for NP0000734 (Xanthine)

HMDB0000292
     RDKit          3D
Xanthine
 15 16  0  0  0  0  0  0  0  0999 V2000
   -3.2608   -0.6489    0.1356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0318   -0.3213    0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7301    0.9667    0.2053 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4297    1.3458    0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1665    2.5720    0.2719 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5787    0.4163    0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9079    0.4767   -0.0695 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4253   -0.7714   -0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845   -1.6464   -0.2530 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2515   -0.9221   -0.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598   -1.2255   -0.0591 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4980    1.6651    0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4796    1.3539   -0.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4697   -1.0301   -0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3205   -2.2309   -0.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
 10  6  2  0
  3 12  1  0
  7 13  1  0
  8 14  1  0
 11 15  1  0
M  END
Download

3D SDF for NP0000734 (Xanthine)

 
  Mrv1652309042000002D          

 11 12  0  0  0  0            999 V2000
   14.2313   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2313  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9738   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4888   -9.2400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9738  -10.7250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4888  -10.5600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6750   -9.4875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9738   -8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9938   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6750  -10.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4175  -10.6837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6  9  2  0  0  0  0
  7 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000734

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1NC2=C(NC=N2)C(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)

> <INCHI_KEY>
LRFVTYWOQMYALW-UHFFFAOYSA-N

> <FORMULA>
C5H4N4O2

> <MOLECULAR_WEIGHT>
152.1109

> <EXACT_MASS>
152.033425392

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
12.702109770186718

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.65

> <JCHEM_LOGP>
-0.20706379166666647

> <ALOGPS_LOGS>
-1.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.765949537699065

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.954237880526347

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7029128013721097

> <JCHEM_POLAR_SURFACE_AREA>
86.88

> <JCHEM_REFRACTIVITY>
36.9219

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.91e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xanthine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000734 (Xanthine)

HMDB0000292
     RDKit          3D
Xanthine
 15 16  0  0  0  0  0  0  0  0999 V2000
   -3.2608   -0.6489    0.1356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0318   -0.3213    0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7301    0.9667    0.2053 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4297    1.3458    0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1665    2.5720    0.2719 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5787    0.4163    0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9079    0.4767   -0.0695 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4253   -0.7714   -0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845   -1.6464   -0.2530 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2515   -0.9221   -0.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598   -1.2255   -0.0591 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4980    1.6651    0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4796    1.3539   -0.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4697   -1.0301   -0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3205   -2.2309   -0.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
 10  6  2  0
  3 12  1  0
  7 13  1  0
  8 14  1  0
 11 15  1  0
M  END
Download

PDB for NP0000734 (Xanthine)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      26.565 -17.710   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.565 -19.250   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      27.951 -16.940   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      25.179 -17.248   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      27.951 -20.020   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      25.179 -19.712   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      29.260 -17.710   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0      27.951 -15.400   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      24.255 -18.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.260 -19.173   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      30.646 -19.943   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10                                                       
CONECT    6    2    9                                                       
CONECT    7    3   10                                                       
CONECT    8    3                                                            
CONECT    9    4    6                                                       
CONECT   10    5   11    7                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END
Download

3D PDB for NP0000734 (Xanthine)

COMPND    HMDB0000292
HETATM    1  O1  UNL     1      -3.261  -0.649   0.136  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.032  -0.321   0.093  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.730   0.967   0.205  1.00  0.00           N  
HETATM    4  C2  UNL     1      -0.430   1.346   0.163  1.00  0.00           C  
HETATM    5  O2  UNL     1      -0.167   2.572   0.272  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.579   0.416   0.007  1.00  0.00           C  
HETATM    7  N2  UNL     1       1.908   0.477  -0.069  1.00  0.00           N  
HETATM    8  C4  UNL     1       2.425  -0.771  -0.228  1.00  0.00           C  
HETATM    9  N3  UNL     1       1.385  -1.646  -0.253  1.00  0.00           N  
HETATM   10  C5  UNL     1       0.252  -0.922  -0.109  1.00  0.00           C  
HETATM   11  N4  UNL     1      -1.060  -1.225  -0.059  1.00  0.00           N  
HETATM   12  H1  UNL     1      -2.498   1.665   0.324  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.480   1.354  -0.016  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.470  -1.030  -0.319  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.321  -2.231  -0.145  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4   12
CONECT    4    5    5    6
CONECT    6    7   10   10
CONECT    7    8   13
CONECT    8    9    9   14
CONECT    9   10
CONECT   10   11
CONECT   11   15
END
Download

SMILES for NP0000734 (Xanthine)

O=C1NC2=C(NC=N2)C(=O)N1
Download

INCHI for NP0000734 (Xanthine)

InChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)
Download
View in JSmol
Synonyms
ValueSource
2,6-DihydroxypurineChEBI
2,6-Dioxo-1,2,3,6-tetrahydropurineChEBI
9H-Purine-2,6-(1H,3H)-dioneChEBI
Purine-2(3H),6(1H)-dioneChEBI
XanChEBI
1H-Purine-2,6-diolHMDB
2,6(1,3)-PurinedionHMDB
2,6-DioxopurineHMDB
3,7-Dihydro-1H-purine-2,6-dioneHMDB
3,7-Dihydropurine-2,6-dioneHMDB
9H-Purine-2,6(1H,3H)-dioneHMDB
9H-Purine-2,6-diolHMDB
DioxopurineHMDB
IsoxanthineHMDB
PseudoxanthineHMDB
Purine-2,6(1H,3H)-dioneHMDB
Purine-2,6-diolHMDB
Xanthic oxideHMDB
XanthinHMDB
Chemical FormulaC5H4N4O2
Average Mass152.1109 Da
Monoisotopic Mass152.03343 Da
IUPAC Name2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Namexanthine
CAS Registry Number69-89-6
SMILES
O=C1NC2=C(NC=N2)C(=O)N1
InChI Identifier
InChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)
InChI KeyLRFVTYWOQMYALW-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-02-09View Spectrum
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, 100%_DMSO, 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
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
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Camellia sinensisKNApSAcK Database
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
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
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephoraFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Eleutherococcus giraldiiLOTUS Database
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Helix pomatiaLOTUS Database
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Homo sapiensLOTUS Database
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Pherethima aspergillum-
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salmonella entericaLOTUS Database
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
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
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
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Trypanosoma bruceiLOTUS Database
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
Velella velellaLOTUS Database
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthium strumariumKNApSAcK Database
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus jujubaLOTUS Database
Ziziphus zizyphusFooDB
Species Where Detected
Species NameSourceReference
Bos taurus domesticusKNApSAcK Database
Escherichia coli K12KNApSAcK Database
Homo sapiens (Serum)KNApSAcK Database
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
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.069 mg/mL at 16 °C; 9.5 mg/mL (sodium salt)Maynard, R. L. (1997). The Merck Index: 1996. Occupational and Environmental Medicine, 54(4), 288.
LogP-0.73Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility4.91 g/LALOGPS
logP-0.65ALOGPS
logP-0.21ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)7.95ChemAxon
pKa (Strongest Basic)-0.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.88 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity36.92 m³·mol⁻¹ChemAxon
Polarizability12.7 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000292
DrugBank IDDB02134
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001977
KNApSAcK IDC00019660
Chemspider ID1151
KEGG Compound IDC00385
BioCyc IDXANTHINE
BiGG ID34825
Wikipedia LinkXanthine
METLIN ID82
PubChem Compound1188
PDB IDNot Available
ChEBI ID17712
Good Scents IDrw1297041
References
General References
  1. Eells JT, Spector R: Purine and pyrimidine base and nucleoside concentrations in human cerebrospinal fluid and plasma. Neurochem Res. 1983 Nov;8(11):1451-7. [PubMed:6656991 ]
  2. Liu Z, Li T, Wang E: Simultaneous determination of guanine, uric acid, hypoxanthine and xanthine in human plasma by reversed-phase high-performance liquid chromatography with amperometric detection. Analyst. 1995 Aug;120(8):2181-4. [PubMed:7677251 ]
  3. Ihara H, Shino Y, Morita Y, Kawaguchi E, Hashizume N, Yoshida M: Is skeletal muscle damaged by the oxidative stress following anaerobic exercise? J Clin Lab Anal. 2001;15(5):239-43. [PubMed:11574951 ]
  4. Niklasson F: Simultaneous liquid-chromatographic determination of hypoxanthine, xanthine, urate, and creatinine in cerebrospinal fluid, with direct injection. Clin Chem. 1983 Aug;29(8):1543-6. [PubMed:6872216 ]
  5. Castro-Gago M, Rodriguez IN, Rodriguez-Nunez A, Guitian JP, Rocamonde SL, Rodriguez-Segade S: Therapeutic criteria in hydrocephalic children. Childs Nerv Syst. 1989 Dec;5(6):361-3. [PubMed:2611770 ]
  6. Kaya M, Moriwaki Y, Ka T, Inokuchi T, Yamamoto A, Takahashi S, Tsutsumi Z, Tsuzita J, Oku Y, Yamamoto T: Plasma concentrations and urinary excretion of purine bases (uric acid, hypoxanthine, and xanthine) and oxypurinol after rigorous exercise. Metabolism. 2006 Jan;55(1):103-7. [PubMed:16324927 ]
  7. Gudbjornsson B, Zak A, Niklasson F, Hallgren R: Hypoxanthine, xanthine, and urate in synovial fluid from patients with inflammatory arthritides. Ann Rheum Dis. 1991 Oct;50(10):669-72. [PubMed:1958086 ]
  8. Teeuwen HW, Elbers EL, van Rossum JM: Rapid and sensitive gas-chromatographic determination of caffeine in blood plasma, saliva, and xanthine beverages. Mol Biol Rep. 1991 Feb;15(1):1-7. [PubMed:1875916 ]
  9. Becker MA, Kisicki J, Khosravan R, Wu J, Mulford D, Hunt B, MacDonald P, Joseph-Ridge N: Febuxostat (TMX-67), a novel, non-purine, selective inhibitor of xanthine oxidase, is safe and decreases serum urate in healthy volunteers. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1111-6. [PubMed:15571211 ]
  10. Kawasaki N, Tanimoto T, Tanaka A, Hayakawa T, Miyasaka N: Determination of non-protein-bound iron in human synovial fluid by high-performance liquid chromatography with electrochemical detection. J Chromatogr B Biomed Appl. 1994 Jun 17;656(2):436-40. [PubMed:7987499 ]
  11. Cooper N, Khosravan R, Erdmann C, Fiene J, Lee JW: Quantification of uric acid, xanthine and hypoxanthine in human serum by HPLC for pharmacodynamic studies. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Jun 6;837(1-2):1-10. Epub 2006 May 2. [PubMed:16631418 ]
  12. Kiss A, Barenyi M, Csontai A: Xanthine stone in the urinary bladder of a male child. Urol Int. 1999;63(4):242-4. [PubMed:10743702 ]
  13. Kjaergaard N, Moller-Petersen JF, Kristiansen FV, Petersen PL, Ekelund S, Skovbo P: Xanthine and hypoxanthine in amniotic fluid during pregnancy. Dan Med Bull. 1990 Dec;37(6):559-60. [PubMed:2127397 ]
  14. Wiley DM, Szabo I, Maguire MH, Finley BE, Bennett TL: Measurement of hypoxanthine and xanthine in late-gestation human amniotic fluid by reversed-phase high-performance liquid chromatography with photodiode-array detection. J Chromatogr. 1990 Nov 30;533:73-86. [PubMed:2081781 ]
  15. Ginsburg I: Could synergistic interactions among reactive oxygen species, proteinases, membrane-perforating enzymes, hydrolases, microbial hemolysins and cytokines be the main cause of tissue damage in infectious and inflammatory conditions? Med Hypotheses. 1998 Oct;51(4):337-46. [PubMed:9824842 ]
  16. Sun Y, Fei J, Wu K, Hu S: Simultaneous electrochemical determination of xanthine and uric acid at a nanoparticle film electrode. Anal Bioanal Chem. 2003 Feb;375(4):544-9. doi: 10.1007/s00216-002-1743-7. Epub 2003 Feb 12. [PubMed:12610708 ]