Showing Compound Card for Xanthine (CDB005230)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (4) Show 6 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:22:22 UTC
Updated at2020-12-07 19:11:48 UTC
CannabisDB IDCDB005230
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameXanthine
DescriptionXanthine, also known as Xan or 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. An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated. Xanthine is an extremely weak basic (essentially neutral) compound (based on its pKa). Xanthine exists in all living species, ranging from bacteria to humans. 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, xanthine is involved in azathioprine action pathway. Xanthine is a potentially toxic compound. Xanthine, with regard to humans, has been found to be associated with several diseases such as hydrocephalus, adenosine kinase deficiency, xanthinuria type II, and eosinophilic esophagitis; xanthine has also been linked to the inborn metabolic disorder lesch-nyhan syndrome. Xanthine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Molecular Weight152.11
Monoisotopic Molecular Weight152.0334
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
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

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)MERCK INDEX (1996); Human Metabolome Project (salt)
logP-0.73HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0udi-7900000000-2d5ab5d5db8ff49814672014-09-20View Spectrum
GC-MSXanthine, non-derivatized, GC-MS Spectrumsplash10-0f6t-0924000000-9b80e0a2a60c73ca0180Spectrum
GC-MSXanthine, non-derivatized, GC-MS Spectrumsplash10-0f6t-0924000000-9b80e0a2a60c73ca0180Spectrum
GC-MSXanthine, non-derivatized, GC-MS Spectrumsplash10-0f6t-0924000000-30dc5892eecde860846aSpectrum
Predicted GC-MSXanthine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0kai-7900000000-2dc30b0fc4cff2239dbeSpectrum
Predicted GC-MSXanthine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-a70539989d121bfacee02012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-6900000000-b047b06406308dbaeda82012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9300000000-ed480ed920c3e9b576ec2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0zfr-0900000000-efb049914c9bce5962672012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfr-0900000000-efb049914c9bce5962672017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0900000000-5fee91293851bb02193e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-0900000000-4568a814903ff411923a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-e078a358156f5a04d4c12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3900000000-250f7dc30d6fd96a4ef62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-0900000000-3a6dad2473c1654789f62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-a4e9443b51c3ac2fc58b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-d23801a49488b1a5f0a22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-4900000000-b177a2a36043e5e87efc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0udi-0900000000-cb3b35c3117b7f36bf5c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0900000000-8d2a19e7c37d2cb7658f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-05mo-9300000000-33d00ab2288aaa0555172021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-1900000000-3a6dad2473c1654789f62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-37e76df2401a85967caa2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0udi-0900000000-4132da06dda895afc3ab2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-2e9e069e2df414aed0372015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w29-0900000000-fa52193346bc456d89e82015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5i-9400000000-bbf70998e8b7515cb4402015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-566d663553ce4f0ec2072015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-1900000000-d0a5d2c0f89f8d42d9032015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-351d9f8ee3470f9118292015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100.7 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Xanthine dehydrogenase/oxidaseXDH2p23.1P47989 details
Hypoxanthine-guanine phosphoribosyltransferaseHPRT1Xq26.1P00492 details
Guanine deaminaseGDA9q21.13Q9Y2T3 details
Purine nucleoside phosphorylasePNP14q13.1P00491 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Xanthine dehydrogenase/oxidaseXDH2p23.1P47989 details
Guanine deaminaseGDA9q21.13Q9Y2T3 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
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
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Xanthine dehydrogenase/oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular weight:
146422.99
Enzyme Details
2. Hypoxanthine-guanine phosphoribosyltransferase
General function:
Involved in hypoxanthine phosphoribosyltransferase activity
Specific function:
Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
Gene Name:
HPRT1
Uniprot ID:
P00492
Molecular weight:
24579.155
Enzyme Details
3. Guanine deaminase
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolytic deamination of guanine, producing xanthine and ammonia (By similarity).
Gene Name:
GDA
Uniprot ID:
Q9Y2T3
Molecular weight:
52836.65
Enzyme Details
4. Purine nucleoside phosphorylase
General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:
PNP
Uniprot ID:
P00491
Molecular weight:
32117.69