You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:24:48 UTC
HMDB IDHMDB00133
Secondary Accession NumbersNone
Metabolite Identification
Common NameGuanosine
DescriptionGuanosine is a nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a beta-N9-glycosidic bond. Guanosine can be phosphorylated to become GMP (guanosine monophosphate), cGMP (cyclic guanosine monophosphate), GDP (guanosine diphosphate) and GTP (guanosine triphosphate). (Wikipedia). The nucleoside guanosine exert important neuroprotective and neuromodulator roles in the central nervous system, which may be related to inhibition of the glutamatergic neurotransmission activity. Guanosine is the specific extracellular guanine-based purines effector and indicate that its conversion occurs not only in the central nervous system but also peripherally. (PMID: 16325434 ).
Structure
Thumb
Synonyms
  1. 2-Amino-1,9-dihydro-9-b-D-ribofuranosyl-6H-purin-6-one
  2. 2-Amino-1,9-dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one
  3. 2-Amino-Inosine
  4. 9-b-D-Ribofuranosyl-Guanine
  5. 9-beta-delta-Ribofuranosyl-Guanine
  6. b-D-Ribofuranoside guanine-9
  7. beta-delta-Ribofuranoside guanine-9
  8. Guanosine
  9. Ribonucleoside
  10. Vernine
Chemical FormulaC10H13N5O5
Average Molecular Weight283.2407
Monoisotopic Molecular Weight283.091668551
IUPAC Name2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
Traditional IUPAC Nameguanosine
CAS Registry Number118-00-3
SMILES
NC1=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1
InChI Identifier
InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1
InChI KeyNYHBQMYGNKIUIF-UUOKFMHZSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPurine Nucleosides and Analogues
Sub ClassN/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Ribonucleosides(KEGG)
  • guanosines(ChEBI)
Substituents
  • 1,2 Diol
  • Aminopyrimidine
  • Glycosyl Compound
  • Hypoxanthine
  • Imidazole
  • Imidazopyrimidine
  • N Glycosyl Compound
  • Oxolane
  • Pentose Monosaccharide
  • Primary Alcohol
  • Purine
  • Purinone
  • Pyrimidine
  • Pyrimidone
  • Saccharide
  • Secondary Alcohol
Direct ParentPurine Nucleosides and Analogues
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Extracellular
  • Mitochondria
  • Lysosome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point239 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.7 mg/mL at 18 °CNot Available
LogP-1.90SANGSTER (1993)
Predicted Properties
PropertyValueSource
water solubility15.3 g/LALOGPS
logP-2.1ALOGPS
logP-2.7ChemAxon
logS-1.3ALOGPS
pKa (strongest acidic)10.16ChemAxon
pKa (strongest basic)1.79ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count8ChemAxon
hydrogen donor count5ChemAxon
polar surface area155.22ChemAxon
rotatable bond count2ChemAxon
refractivity64.62ChemAxon
polarizability26.02ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
  • Lysosome
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
  • Urine
Tissue Location
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050map00230
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.8 +/- 0.5 uMAdult (>18 years old)BothNormal details
Cellular CytoplasmDetected and Quantified4.5 +/- 2.9 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.13 (0.022-0.23) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.06 +/- 0.02 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.05 +/- 0.02 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.06 +/- 0.02 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified35.0 - 2588.0 umol/mmol creatinineAdult (>18 years old)BothPurine nucleoside phosphorylase (PNP) deficiency details
UrineDetected and Quantified35-588 umol/mmol creatinineAdult (>18 years old)BothPurine nucleoside phosphorylase (PNP) deficiency details
Associated Disorders and Diseases
Disease References
Purine nucleoside phosphorylase deficiency
  1. Wevers RA, Engelke UF, Moolenaar SH, Brautigam C, de Jong JG, Duran R, de Abreu RA, van Gennip AH: 1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. Clin Chem. 1999 Apr;45(4):539-48. Pubmed: 10102915
Associated OMIM IDs
  • 164050 (Purine nucleoside phosphorylase deficiency )
DrugBank IDDB02857
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003632
KNApSAcK IDNot Available
Chemspider ID6544
KEGG Compound IDC00387
BioCyc IDGUANOSINE
BiGG ID51567
Wikipedia LinkGuanosine
NuGOwiki LinkHMDB00133
Metagene LinkHMDB00133
METLIN ID87
PubChem Compound6802
PDB IDGMP
ChEBI ID16750
References
Synthesis ReferenceTang, Shengrong; Huang, Weihong; Hou, Zuorong. Process of guanosine production by fermentation. Gongye Weishengwu (1998), 28(4), 11-16.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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
  2. Lee SH, Jung BH, Kim SY, Chung BC: A rapid and sensitive method for quantitation of nucleosides in human urine using liquid chromatography/mass spectrometry with direct urine injection. Rapid Commun Mass Spectrom. 2004;18(9):973-7. Pubmed: 15116424
  3. Traut TW: Physiological concentrations of purines and pyrimidines. Mol Cell Biochem. 1994 Nov 9;140(1):1-22. Pubmed: 7877593
  4. Wevers RA, Engelke UF, Moolenaar SH, Brautigam C, de Jong JG, Duran R, de Abreu RA, van Gennip AH: 1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. Clin Chem. 1999 Apr;45(4):539-48. Pubmed: 10102915
  5. Hartwick RA, Krstulovic AM, Brown PR: Identification and quantitation of nucleosides, bases and other UV-absorbing compounds in serum, using reversed-phase high-performance liquid chromatography. II. Evaluation of human sera. J Chromatogr. 1979 Dec 30;186:659-76. Pubmed: 546939
  6. Saute JA, da Silveira LE, Soares FA, Martini LH, Souza DO, Ganzella M: Amnesic effect of GMP depends on its conversion to guanosine. Neurobiol Learn Mem. 2006 May;85(3):206-12. Epub 2005 Dec 1. Pubmed: 16325434

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:
NT5E
Uniprot ID:
P21589
Molecular weight:
57948.125
Reactions
Guanosine monophosphate + Water → Guanosine + Phosphoric aciddetails
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides. Helps to regulate adenosine levels (By similarity).
Gene Name:
NT5C1B
Uniprot ID:
Q96P26
Molecular weight:
68803.055
Reactions
Guanosine monophosphate + Water → Guanosine + Phosphoric aciddetails
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides and has a broad substrate specificity. Helps to regulate adenosine levels in heart during ischemia and hypoxia.
Gene Name:
NT5C1A
Uniprot ID:
Q9BXI3
Molecular weight:
41020.145
Reactions
Guanosine monophosphate + Water → Guanosine + Phosphoric aciddetails
General function:
Involved in metal ion binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:
NT5C
Uniprot ID:
Q8TCD5
Molecular weight:
Not Available
Reactions
Guanosine monophosphate + Water → Guanosine + Phosphoric aciddetails
General function:
Involved in phosphatase activity
Specific function:
Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:
NT5M
Uniprot ID:
Q9NPB1
Molecular weight:
Not Available
Reactions
Guanosine monophosphate + Water → Guanosine + Phosphoric aciddetails
General function:
Involved in magnesium ion binding
Specific function:
Can act both as nucleotidase and as phosphotransferase.
Gene Name:
NT5C3
Uniprot ID:
Q9H0P0
Molecular weight:
33914.91
Reactions
Guanosine monophosphate + Water → Guanosine + Phosphoric aciddetails
General function:
Involved in 5'-nucleotidase activity
Specific function:
May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:
NT5C2
Uniprot ID:
P49902
Molecular weight:
64969.2
Reactions
Guanosine monophosphate + Water → Guanosine + Phosphoric aciddetails
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
Reactions
Guanosine + Phosphoric acid → Guanine + Ribose 1-phosphatedetails
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423