Record Information
Version1.0
Creation date2010-04-08 22:05:11 UTC
Update date2019-11-26 02:56:50 UTC
Primary IDFDB001977
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameXanthine
DescriptionXanthine 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Xanthine is found, on average, in the highest concentration within milk (cow). Xanthine has also been detected, but not quantified in, several different foods, such as fenugreeks, ucuhuba, roselles, allspices, and garland chrysanthemums. This could make xanthine a potential biomarker for the consumption of these foods.
CAS Number69-89-6
Structure
Thumb
Synonyms
SynonymSource
1H-Purine-2,6-diolHMDB
1H-Purine-2,6-dione, 3,7-dihydro-biospider
1H-Purine-2,6-dione, 3,9-dihydro-biospider
2-Oxohypoxanthinebiospider
2,6-Dihydroxypurinedb_source
2,6-Dioxo-1,2,3, 6-tetrahydropurinebiospider
2,6-Dioxo-1,2,3,6-tetrahydropurinebiospider
2,6-Dioxopurinebiospider
2,6-Purinedioldb_source
2,6(1,3)-PurinedionHMDB
3,7-dihydro-1H-Purine-2,6-dioneHMDB
3,7-Dihydro-1H-purine-2,6-dione, 9CIdb_source
3,7-Dihydropurine-2,6-dionebiospider
3,9-Dihydro-1H-purine-2,6-dionebiospider
3,9-Dihydro-purine-2,6-dionebiospider
7H-xanthinebiospider
9H-Purine-2,6-(1H,3H)-dionebiospider
9H-Purine-2,6-diolbiospider
9H-Purine-2,6(1H,3H)-dioneHMDB
9H-Xanthinebiospider
Dioxopurinebiospider
IsoxanthineHMDB
PseudoxanthineHMDB
Purine-2,6-(1H,3H)-dionebiospider
Purine-2,6-diolHMDB
Purine-2,6(1H,3H)-dionebiospider
Purine-2(3H),6(1H)-dionebiospider
XanChEBI
Xanthic oxideHMDB
XanthinHMDB
Predicted Properties
PropertyValueSource
Water Solubility9.54 g/LALOGPS
logP-0.29ALOGPS
logP0.37ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)8.77ChemAxon
pKa (Strongest Basic)0.57ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.92 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.81 m³·mol⁻¹ChemAxon
Polarizability12.94 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H12N12O6
IUPAC nametris(9H-purine-2,6-diol)
InChI IdentifierInChI=1S/3C5H4N4O2/c3*10-4-2-3(7-1-6-2)8-5(11)9-4/h3*1H,(H3,6,7,8,9,10,11)
InChI KeyKPILEYHQAXBFOG-UHFFFAOYSA-N
Isomeric SMILESOC1=NC(=O)NC2=C1N=CN2.O=C1NC2=C(N=CN2)C(=O)N1.O=C1NC2=C(NC=N2)C(=O)N1
Average Molecular Weight456.3326
Monoisotopic Molecular Weight456.100276176
Classification
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 FrameworkNot Available
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 39.48%; H 2.65%; N 36.83%; O 21.04%DFC
Melting PointMp 350°DFC
Boiling PointNot Available
Experimental Water Solubility0.069 mg/mL at 16 oCMERCK INDEX (1996)
Experimental logP-0.73HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID1151
ChEMBL IDCHEMBL1424
KEGG Compound IDC00385
Pubchem Compound ID1188
Pubchem Substance IDNot Available
ChEBI ID17712
Phenol-Explorer IDNot Available
DrugBank IDDB02134
HMDB IDHMDB00292
CRC / DFC (Dictionary of Food Compounds) IDCBV75-B:CBV75-B
EAFUS IDNot Available
Dr. Duke IDXANTHINE
BIGG ID34825
KNApSAcK IDC00019660
HET IDXAN
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDXanthine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
Enzymes
NameGene NameUniProt ID
Purine nucleoside phosphorylasePNPP00491
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050 map00230
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).