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Human Metabolome Database Version 3.5

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Showing metabocard for Guanine (HMDB00132)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:57 -0700
HMDB ID HMDB00132
Secondary Accession Numbers None
Metabolite Identification
Common Name Guanine
Description Guanine is one of the five main nucleobases found in the nucleic acids DNA and RNA. Guanine is a derivative of purine, consisting of a fused pyrimidine-imidazole ring system with conjugated double bonds. Being unsaturated, the bicyclic molecule is planar. The guanine nucleoside is called guanosine. The first isolation of guanine was reported in 1844 from the excreta of sea birds, known as guano, which was used as a source of fertilizer. High affinity binding of guanine nucleotides and the ability to hydrolyze bound GTP to GDP are characteristics of an extended family of intracellular proteins. Guanine nucleotide-binding regulatory proteins may be involved in the activation of phospholipases C and A2 by hormones and other ligands. The binding of hormones to receptors that activate phospholipase C is decreased by guanine nucleotides and these hormones also stimulate a high-affinity GTPase activity in cell membranes. Effects of hormones on phospholipase C activity in cell-free preparations are dependent on the presence of guanine nucleotides. Hypoxanthine-guanine phosphoribosyltransferase (HPRT, EC 2.4.2.8) is a purine salvage enzyme that catalyses the conversion of hypoxanthine and guanine to their respective mononucleotides. Partial deficiency of this enzyme can result in the overproduction of uric acid leading to a severe form of gout, whilst a virtual absence of HPRT activity causes the Lesch-Nyhan syndrome which is characterised by hyperuricaemia, mental retardation, choreoathetosis and compulsive self-mutilation. Peroxynitrite induces DNA base damage predominantly at guanine (G) and 8-oxoguanine (8-oxoG) nucleobases via oxidation reactions. G and 8-oxoG are the most reactive bases toward Peroxynitrite and possibly the major contributors to peroxynitrite-derived genotoxic and mutagenic lesions. The neutral G radical, reacts with NO2 to yield 8-nitroguanine and 5-nitro-4-guanidinohydantoin. (PMID: 16352449 Link_out, 2435586 Link_out, 2838362 Link_out, 1487231 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-Amino-1,7-dihydro-6H-Purin-6-one
  2. 2-Amino-1,9-dihydro-6H-purin-6-one
  3. 2-Amino-1,9-dihydro-purin-6-one
  4. 2-Amino-3,7-dihydro-6H-purin-6-one
  5. 2-Amino-6-hydroxy-1H-purine
  6. 2-Amino-6-hydroxypurine
  7. 2-Amino-6-purinol
  8. 2-Amino-Hypoxanthine
  9. 2-Aminohypoxanthine
  10. 6-Hydroxy-2-aminopurine
  11. C.I. Natural White 1
  12. CI Natural white 1
  13. Dew Pearl
  14. GUA
  15. Guanin
  16. Guanine
  17. Guanine enol
  18. GUN
  19. Mearlmaid
  20. Mearlmaid AA
  21. Natural pearl essence
  22. Natural White 1
  23. Naturon
  24. Pathocidin
  25. Pearl Essence
  26. Stella Polaris
Chemical Formula C5H5N5O
Average Molecular Weight 151.1261
Monoisotopic Molecular Weight 151.049409807
IUPAC Name 2-amino-6,7-dihydro-3H-purin-6-one
Traditional IUPAC Name 2-amino-3,7-dihydropurin-6-one
CAS Registry Number 73-40-5
SMILES NC1=NC(=O)C2=C(N1)N=CN2
InChI Identifier InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChI Key UYTPUPDQBNUYGX-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Imidazopyrimidines
Sub Class Purines and Purine Derivatives
Other Descriptors
  • 2-aminopurines(ChEBI)
  • Aromatic Heteropolycyclic Compounds
  • Hypoxanthines
  • Organic Compounds
  • Purines(KEGG)
  • a purine base(Cyc)
  • a purine(Cyc)
  • oxopurine(ChEBI)
  • purine nucleobase(ChEBI)
Substituents
  • Aminopyrimidine
  • Imidazole
  • Pyrimidine
  • Pyrimidone
Direct Parent Purinones
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Extracellular
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 360 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 2.08 mg/mL at 37 °C Not Available
LogP -0.91 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 2.31 g/L ALOGPS
LogP -0.92 ALOGPS
LogP -0.59 ChemAxon
LogS -1.82 ALOGPS
pKa (strongest acidic) 8.95 ChemAxon
pKa (strongest basic) 2.22 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 96.16 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 38.9 ChemAxon
Polarizability 13.34 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
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)
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
  • Extracellular
Biofluid Locations
  • Cellular Cytoplasm
  • Urine
Tissue Location
  • Muscle
  • Fibroblasts
  • Intestine
  • Neuron
  • Testes
  • Epidermis
  • Myelin
  • Prostate
  • Spleen
Pathways
Name SMPDB Link KEGG Link
Purine Metabolism SMP00050 map00230 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Cellular Cytoplasm Detected and Quantified
Article_icon
97 uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.20 (0.085-0.26) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.37 (0.18-0.57) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
1.92 (0.99-2.86) umol/mmol creatinine Not Specified Both Lesch-Nyhan syndrome Not Available
Associated Disorders and Diseases
Disease References
Lesch-Nyhan syndrome
  • Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005 Link_out
    Associated OMIM IDs
    DrugBank ID DB02377 Link_out
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB004222
    KNApSAcK ID Not Available
    Chemspider ID 744 Link_out
    KEGG Compound ID C00242 Link_out
    BioCyc ID GUANINE Link_out
    BiGG ID 34363 Link_out
    Wikipedia Link Guanine Link_out
    NuGOwiki Link HMDB00132 Link_out
    Metagene Link HMDB00132 Link_out
    METLIN ID 315 Link_out
    PubChem Compound 764 Link_out
    PDB ID GUN Link_out
    ChEBI ID 16235 Link_out
    References
    Synthesis Reference Xiao, Xuhua; Ma, Weiyong. One-pot synthesis of guanine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp.
    Material Safety Data Sheet (MSDS) Download (PDF)
    General References
    1. Boulias C, Moscarello MA: Guanine nucleotides stimulate hydrolysis of phosphatidyl inositol bis phosphate in human myelin membranes. Biochem Biophys Res Commun. 1989 Jul 14;162(1):282-7. Pubmed: 2546548 Link_out
    2. Harkness RA: Hypoxanthine, xanthine and uridine in body fluids, indicators of ATP depletion. J Chromatogr. 1988 Jul 29;429:255-78. Pubmed: 3062020 Link_out
    3. Castro-Gago M, Cid E, Trabazo S, Pavon P, Camina F, Rodriguez-Segade S, Einis Punal J, Rodriguez-Nunez A: Cerebrospinal fluid purine metabolites and pyrimidine bases after brief febrile convulsions. Epilepsia. 1995 May;36(5):471-4. Pubmed: 7614924 Link_out
    4. Steyn LM, Harley EH: Intracellular activity of HPRT Cape Town: purine uptake and growth of cultured cells in selective media. J Inherit Metab Dis. 1985;8(4):198-203. Pubmed: 3939543 Link_out
    5. Yafe A, Etzioni S, Weisman-Shomer P, Fry M: Formation and properties of hairpin and tetraplex structures of guanine-rich regulatory sequences of muscle-specific genes. Nucleic Acids Res. 2005 May 20;33(9):2887-900. Print 2005. Pubmed: 15908587 Link_out
    6. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005 Link_out
    7. Russo TA, Jodush ST, Brown JJ, Johnson JR: Identification of two previously unrecognized genes (guaA and argC) important for uropathogenesis. Mol Microbiol. 1996 Oct;22(2):217-29. Pubmed: 8930907 Link_out
    8. 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
    9. Parkinson SJ, Waldman SA: An intracellular adenine nucleotide binding site inhibits guanyly cyclase C by a guanine nucleotide-dependent mechanism. Biochemistry. 1996 Mar 12;35(10):3213-21. Pubmed: 8605156 Link_out
    10. Rodriguez-Nunez A, Camina F, Lojo S, Rodriguez-Segade S, Castro-Gago M: Concentrations of nucleotides, nucleosides, purine bases and urate in cerebrospinal fluid of children with meningitis. Acta Paediatr. 1993 Oct;82(10):849-52. Pubmed: 8241644 Link_out
    11. Groopman JD, Zhu JQ, Donahue PR, Pikul A, Zhang LS, Chen JS, Wogan GN: Molecular dosimetry of urinary aflatoxin-DNA adducts in people living in Guangxi Autonomous Region, People's Republic of China. Cancer Res. 1992 Jan 1;52(1):45-52. Pubmed: 1727385 Link_out
    12. Shioya M, Wakabayashi K, Yamashita K, Nagao M, Sugimura T: Formation of 8-hydroxydeoxyguanosine in DNA treated with fecapentaene-12 and -14. Mutat Res. 1989 Mar;225(3):91-4. Pubmed: 2927433 Link_out
    13. Allgayer H, Kolb M, Stuber V, Kruis W: Effects of bile acids on base hydroxylation in a model of human colonic mucosal DNA. Cancer Detect Prev. 2002;26(1):85-9. Pubmed: 12088208 Link_out
    14. Schei MA, Hessen JO, Lund E: House-dust mites and mattresses. Allergy. 2002 Jun;57(6):538-42. Pubmed: 12028120 Link_out
    15. Weimann A, Belling D, Poulsen HE: Quantification of 8-oxo-guanine and guanine as the nucleobase, nucleoside and deoxynucleoside forms in human urine by high-performance liquid chromatography-electrospray tandem mass spectrometry. Nucleic Acids Res. 2002 Jan 15;30(2):E7. Pubmed: 11788733 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: Adenine phosphoribosyltransferase
    Reactions:
    • AMP + diphosphate = adenine + 5-phospho-alpha-D-ribose 1-diphosphate [RN:R00190]
    Gene Name: APRT
    Uniprot ID: P07741 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
    Name: Queuine tRNA-ribosyltransferase
    Reactions:
    • (1) [tRNA]-guanine + queuine = [tRNA]-queuine + guanine [RN:R03789]
    • (2) [tRNA]-guanine + 7-aminomethyl-7-carbaguanine = [tRNA]-7-aminomethyl-7-carbaguanine + guanine
    Gene Name: QTRT1
    Uniprot ID: Q9BXR0 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: GTP cyclohydrolase 1
    Reactions:
    • GTP + H2O = formate + 7,8-dihydroneopterin 3'-triphosphate [RN:R00424]
    Gene Name: GCH1
    Uniprot ID: P30793 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Guanine nucleotide-binding protein G(s) subunit alpha isoforms short
    Reactions:
      Gene Name: GNAS
      Uniprot ID: P63092 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Guanine nucleotide-binding protein G(q) subunit alpha
      Reactions:
        Gene Name: GNAQ
        Uniprot ID: P50148 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Purine nucleoside phosphorylase
        Reactions:
        • purine nucleoside + phosphate = purine + alpha-D-ribose 1-phosphate [RN:R08368]
        Gene Name: PNP
        Uniprot ID: P00491 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Guanine nucleotide-binding protein G(i) subunit alpha-1
        Reactions:
          Gene Name: GNAI1
          Uniprot ID: P63096 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA