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Human Metabolome Database Version 3.5

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Showing metabocard for Xanthine (HMDB00292)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:15 -0700
HMDB ID HMDB00292
Secondary Accession Numbers None
Metabolite Identification
Common Name Xanthine
Description Xanthine is a purine base found in most body tissues and fluids, certain plants, and some urinary calculi. It is an intermediate in the degradation of adenosine monophosphate to uric acid, being formed by oxidation of hypoxanthine. The methylated xanthine compounds caffeine, theobromine, and theophylline and their derivatives are used in medicine for their bronchodilator effects. (Dorland, 28th ed.).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1H-Purine-2,6-diol
  2. 2,6(1,3)-Purinedion
  3. 2,6-Dihydroxypurine
  4. 2,6-Dioxopurine
  5. 3,7-Dihydro-1H-purine-2,6-dione
  6. 3,7-Dihydropurine-2,6-dione
  7. 9H-Purine-2,6(1H,3H)-dione
  8. 9H-Purine-2,6-diol
  9. Dioxopurine
  10. Isoxanthine
  11. Pseudoxanthine
  12. Purine-2,6(1H,3H)-dione
  13. Purine-2,6-diol
  14. Xanthic oxide
  15. Xanthin
  16. Xanthine
Chemical Formula C5H4N4O2
Average Molecular Weight 152.1109
Monoisotopic Molecular Weight 152.033425392
IUPAC Name 2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional IUPAC Name xanthine
CAS Registry Number 69-89-6
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 Key LRFVTYWOQMYALW-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Imidazopyrimidines
Sub Class Purines and Purine Derivatives
Other Descriptors
  • Organic Compounds
  • Purine alkaloids(KEGG)
  • Purinones
  • a small molecule(Cyc)
  • xanthine(ChEBI)
Substituents
  • Imidazole
  • Pyrimidine
  • Pyrimidone
Direct Parent Xanthines
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Purine metabolism
Application Not Available
Cellular locations
  • Cytoplasm
  • Peroxisome
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point > 300 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.069 mg/mL at 16 °C; 9.5 mg/mL (sodium salt) MERCK INDEX (1996); Human Metabolome Project (salt)
LogP -0.73 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 4.91 g/L ALOGPS
LogP -0.65 ALOGPS
LogP -0.21 ChemAxon
LogS -1.49 ALOGPS
pKa (strongest acidic) 7.95 ChemAxon
pKa (strongest basic) -0.7 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 86.88 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 36.92 ChemAxon
Polarizability 12.7 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Peroxisome
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Skeletal Muscle
  • Bladder
  • Fibroblasts
  • Intestine
  • Testes
  • Kidney
  • Epidermis
  • Prostate
Pathways
Name SMPDB Link KEGG Link
Purine Metabolism SMP00050 map00230 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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5.00 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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1.27 +/- 0.78 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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0.35 +/- 0.19 uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
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0.91 +/- 0.45 uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
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1.07 +/- 0.21 uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
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0.45 (2.7-8.0) uM Adult (>18 years old) Female Normal Not Available
Blood Detected and Quantified
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0.99 +/- 0.48 uM Adult (>18 years old) Male Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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5.20 (4.33-6.07) uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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13 +/- 7 uM Not Specified Both Normal Not Available
Urine Detected and Quantified
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2.6 (2.2-3.75) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Male Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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2.2 +/- 0.3 uM Adult (>18 years old) Both Lesch-Nyhan syndrome Not Available
Blood Detected and Quantified
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51.2 uM Adult (>18 years old) Not Specified Heart Transplant Not Available
Blood Detected and Quantified
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25.00 (10.00-40.00) uM Adult (>18 years old) Both Xanthinuria Type I Not Available
Blood Detected and Quantified
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6.37 +/- 1.95 uM Adult (>18 years old) Both Canavan disease Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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5.17 (3.64-6.70) uM Adult (>18 years old) Both Hydrocephalus Self-compensated hydrocephalics
Cerebrospinal Fluid (CSF) Detected and Quantified
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9.90 (7.46-12.3) uM Children (1-13 year old) Both Hydrocephalus Non-compensated hydrocephalic infants and...
Cerebrospinal Fluid (CSF) Detected and Quantified
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2.30 (2.10-2.50) uM Adult (>18 years old) Both Degenerative disc disease Not Available
Urine Detected and Quantified
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2.9 (1.3-4.6) umol/mmol creatinine Adult (>18 years old) Both Xanthinuria type I Not Available
Urine Detected and Quantified
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131.5 (65.7-197.00) umol/mmol creatinine Adult (>18 years old) Both Xanthinuria Type I Not Available
Associated Disorders and Diseases
Disease References
Degenerative disc disease
  • 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 Link_out
    Hydrocephalus
    • 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 Link_out
      Lesch-Nyhan syndrome
      • Harkness RA, McCreanor GM, Watts RW: Lesch-Nyhan syndrome and its pathogenesis: purine concentrations in plasma and urine with metabolite profiles in CSF. J Inherit Metab Dis. 1988;11(3):239-52. Pubmed: 3148065 Link_out
        Canavan disease
        • Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1. Pubmed: 16139832 Link_out
          Xanthinuria type 1
            • http://www.metagene.de/program/d.prg?mp=XANTHINURIA%20TYPE%20I
            Associated OMIM IDs
            DrugBank ID DB02134 Link_out
            Phenol Explorer Compound ID Not Available
            Phenol Explorer Metabolite ID Not Available
            FoodDB ID FDB001977
            KNApSAcK ID C00019660 Link_out
            Chemspider ID 1151 Link_out
            KEGG Compound ID C00385 Link_out
            BioCyc ID XANTHINE Link_out
            BiGG ID 34825 Link_out
            Wikipedia Link Xanthine Link_out
            NuGOwiki Link HMDB00292 Link_out
            Metagene Link HMDB00292 Link_out
            METLIN ID 82 Link_out
            PubChem Compound 1188 Link_out
            PDB ID XAN Link_out
            ChEBI ID 17712 Link_out
            References
            Synthesis Reference Procedure for the production of xanthine and xanthine-like materials. Fr. (1967), 4 pp.
            Material Safety Data Sheet (MSDS) Download (PDF)
            General References
            1. 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 Link_out
            2. 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 Link_out
            3. 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 Link_out
            4. 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 Link_out
            5. 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 Link_out
            6. 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 Link_out
            7. 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 Link_out
            8. 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 Link_out
            9. 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 Link_out
            10. 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 Link_out
            11. 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 Link_out
            12. 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 Link_out
            13. 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 Link_out
            14. 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 Link_out
            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 Link_out
            16. 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. Pubmed: 19212411 Link_out
            Enzymes
            Name: Xanthine dehydrogenase/oxidase
            Reactions:
            • xanthine + H2O + O2 = urate + H2O2 [RN:R02107]
            Gene Name: XDH
            Uniprot ID: P47989 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Hypoxanthine-guanine phosphoribosyltransferase
            Reactions:
            • IMP + diphosphate = hypoxanthine + 5-phospho-alpha-D-ribose 1-diphosphate [RN:R01132]
            Gene Name: HPRT1
            Uniprot ID: P00492 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Guanine deaminase
            Reactions:
            • guanine + H2O = xanthine + NH3 [RN:R01676]
            Gene Name: GDA
            Uniprot ID: Q9Y2T3 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA