Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:24:48 UTC
HMDB IDHMDB00132
Secondary Accession NumbersNone
Metabolite Identification
Common NameGuanine
DescriptionGuanine 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 , 2435586 , 2838362 , 1487231 ).
Structure
Thumb
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 FormulaC5H5N5O
Average Molecular Weight151.1261
Monoisotopic Molecular Weight151.049409807
IUPAC Name2-amino-6,7-dihydro-3H-purin-6-one
Traditional IUPAC Name2-amino-3,7-dihydropurin-6-one
CAS Registry Number73-40-5
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 KeyUYTPUPDQBNUYGX-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassImidazopyrimidines
Sub ClassPurines 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 ParentPurinones
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point360 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.08 mg/mL at 37 °CNot Available
LogP-0.91HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility2.31 g/LALOGPS
logP-0.92ALOGPS
logP-0.59ChemAxon
logS-1.8ALOGPS
pKa (strongest acidic)8.95ChemAxon
pKa (strongest basic)2.22ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count3ChemAxon
polar surface area96.16ChemAxon
rotatable bond count0ChemAxon
refractivity38.9ChemAxon
polarizability13.34ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Cellular Cytoplasm
  • Urine
Tissue Location
  • Epidermis
  • Fibroblasts
  • Intestine
  • Muscle
  • Myelin
  • Neuron
  • Prostate
  • Spleen
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050map00230
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
Cellular CytoplasmDetected and Quantified97 uMAdult (>18 years old)BothNormal
UrineDetected and Quantified0.20 (0.085-0.26) umol/mmol creatinineAdult (>18 years old)BothNormal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
UrineDetected and Quantified0.37 (0.18-0.57) umol/mmol creatinineAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
UrineDetected and Quantified1.92 (0.99-2.86) umol/mmol creatinineNot SpecifiedBothLesch-Nyhan syndrome
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
Associated OMIM IDs
DrugBank IDDB02377
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB004222
KNApSAcK IDNot Available
Chemspider ID744
KEGG Compound IDC00242
BioCyc IDGUANINE
BiGG ID34363
Wikipedia LinkGuanine
NuGOwiki LinkHMDB00132
Metagene LinkHMDB00132
METLIN ID315
PubChem Compound764
PDB IDGUN
ChEBI ID16235
References
Synthesis ReferenceXiao, Xuhua; Ma, Weiyong. One-pot synthesis of guanine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sculley DG, Dawson PA, Emmerson BT, Gordon RB: A review of the molecular basis of hypoxanthine-guanine phosphoribosyltransferase (HPRT) deficiency. Hum Genet. 1992 Nov;90(3):195-207. Pubmed: 1487231
  2. 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
  3. 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
  4. 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
  5. Harkness RA: Hypoxanthine, xanthine and uridine in body fluids, indicators of ATP depletion. J Chromatogr. 1988 Jul 29;429:255-78. Pubmed: 3062020
  6. 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
  7. 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
  8. 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
  9. 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
  10. 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
  11. 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
  12. 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
  13. 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
  14. 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
  15. 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
  16. Schei MA, Hessen JO, Lund E: House-dust mites and mattresses. Allergy. 2002 Jun;57(6):538-42. Pubmed: 12028120
  17. 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
  18. Niles JC, Wishnok JS, Tannenbaum SR: Peroxynitrite-induced oxidation and nitration products of guanine and 8-oxoguanine: structures and mechanisms of product formation. Nitric Oxide. 2006 Mar;14(2):109-21. Epub 2005 Dec 13. Pubmed: 16352449
  19. Spiegel AM: Signal transduction by guanine nucleotide binding proteins. Mol Cell Endocrinol. 1987 Jan;49(1):1-16. Pubmed: 2435586
  20. Fain JN, Wallace MA, Wojcikiewicz RJ: Evidence for involvement of guanine nucleotide-binding regulatory proteins in the activation of phospholipases by hormones. FASEB J. 1988 Jul;2(10):2569-74. Pubmed: 2838362

Enzymes

Gene Name:
APRT
Uniprot ID:
P07741
Reactions
Guanosine monophosphate + Pyrophosphate unknown Guanine + Phosphoribosyl pyrophosphatedetails
Gene Name:
HPRT1
Uniprot ID:
P00492
Reactions
Guanosine monophosphate + Pyrophosphate unknown Guanine + Phosphoribosyl pyrophosphatedetails
Gene Name:
GDA
Uniprot ID:
Q9Y2T3
Reactions
Guanine + Water unknown Xanthine + Ammoniadetails
Gene Name:
QTRT1
Uniprot ID:
Q9BXR0
Reactions
Guanine(34) in tRNA + Queuine unknown queuosine(34) in tRNA + Guaninedetails
tRNA guanine + Queuine unknown tRNA queuine + Guaninedetails
tRNA guanine + 7-Aminomethyl-7-carbaguanine unknown tRNA 7-aminomethyl-7-carbaguanine + Guaninedetails
Gene Name:
GCH1
Uniprot ID:
P30793
Gene Name:
PNP
Uniprot ID:
P00491
Reactions
Deoxyguanosine + Phosphoric acid unknown Guanine + Deoxyribose 1-phosphatedetails
Guanosine + Phosphoric acid unknown Guanine + Ribose 1-phosphatedetails
Gene Name:
QTRTD1
Uniprot ID:
Q9H974
Reactions
Guanine(34) in tRNA + Queuine unknown queuosine(34) in tRNA + Guaninedetails
tRNA guanine + Queuine unknown tRNA queuine + Guaninedetails
tRNA guanine + 7-Aminomethyl-7-carbaguanine unknown tRNA 7-aminomethyl-7-carbaguanine + Guaninedetails