Human Metabolome Database Version 3.5

Showing metabocard for Guanosine (HMDB00133)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:24:48 -0600
HMDB ID HMDB00133
Secondary Accession Numbers None
Metabolite Identification
Common Name Guanosine
Description Guanosine 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 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C10H13N5O5
Average Molecular Weight 283.2407
Monoisotopic Molecular Weight 283.091668551
IUPAC Name 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
Traditional IUPAC Name guanosine
CAS Registry Number 118-00-3
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 Key NYHBQMYGNKIUIF-UUOKFMHZSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Purine Nucleosides and Analogues
Sub Class N/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 Parent Purine Nucleosides and Analogues
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Extracellular
  • Mitochondria
  • Lysosome
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 239 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.7 mg/mL at 18 °C Not Available
LogP -1.90 SANGSTER (1993)
Predicted Properties
Property Value Source
Water Solubility 15.3 g/L ALOGPS
LogP -2.06 ALOGPS
LogP -2.7 ChemAxon
LogS -1.27 ALOGPS
pKa (strongest acidic) 10.16 ChemAxon
pKa (strongest basic) 1.79 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 155.22 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 64.62 ChemAxon
Polarizability 26.02 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
13C NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
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)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
  • Lysosome
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
  • Urine
Tissue Location
  • Prostate
Pathways
Name SMPDB Link KEGG Link
Purine Metabolism SMP00050 map00230 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.8 +/- 0.5 uM Adult (>18 years old) Both Normal
Cellular Cytoplasm Detected and Quantified
4.5 +/- 2.9 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.13 (0.022-0.23) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.06 +/- 0.02 umol/mmol creatinine Adult (>18 years old) Female Normal
Urine Detected and Quantified
0.05 +/- 0.02 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.06 +/- 0.02 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected and Quantified 35.0 - 2588.0 umol/mmol creatinine Adult (>18 years old) Both Purine-nucleoside phosphorylase (PNP; EC 2.4.2.1) deficiency.
Urine Detected and Quantified 35-588 umol/mmol creatinine Adult (>18 years old) Both Purine-nucleoside phosphorylase deficiency
Associated Disorders and Diseases
Disease References
Purine nucleoside phosphorylase deficiency
  • 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 Link_out
      Associated OMIM IDs
      • 164050 Link_out (Purine nucleoside phosphorylase deficiency )
      DrugBank ID DB02857 Link_out
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB003632
      KNApSAcK ID Not Available
      Chemspider ID 6544 Link_out
      KEGG Compound ID C00387 Link_out
      BioCyc ID GUANOSINE Link_out
      BiGG ID 51567 Link_out
      Wikipedia Link Guanosine Link_out
      NuGOwiki Link HMDB00133 Link_out
      Metagene Link HMDB00133 Link_out
      METLIN ID 87 Link_out
      PubChem Compound 6802 Link_out
      PDB ID GMP Link_out
      ChEBI ID 16750 Link_out
      References
      Synthesis Reference Tang, 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. 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 Link_out
      2. 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 Link_out
      3. 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 Link_out
      4. Traut TW: Physiological concentrations of purines and pyrimidines. Mol Cell Biochem. 1994 Nov 9;140(1):1-22. Pubmed: 7877593 Link_out
      5. 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
      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 Link_out

      Enzymes
      Name: 5'-nucleotidase
      Reactions:
      Guanosine monophosphate + Water unknown Guanosine + Phosphoric acid details
      Gene Name: NT5E
      Uniprot ID: P21589 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cytosolic 5'-nucleotidase 1B
      Reactions:
      Guanosine monophosphate + Water unknown Guanosine + Phosphoric acid details
      Gene Name: NT5C1B
      Uniprot ID: Q96P26 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cytosolic 5'-nucleotidase 1A
      Reactions:
      Guanosine monophosphate + Water unknown Guanosine + Phosphoric acid details
      Gene Name: NT5C1A
      Uniprot ID: Q9BXI3 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 5'(3')-deoxyribonucleotidase, cytosolic type
      Reactions:
      Guanosine monophosphate + Water unknown Guanosine + Phosphoric acid details
      Gene Name: NT5C
      Uniprot ID: Q8TCD5 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 5'(3')-deoxyribonucleotidase, mitochondrial
      Reactions:
      Guanosine monophosphate + Water unknown Guanosine + Phosphoric acid details
      Gene Name: NT5M
      Uniprot ID: Q9NPB1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cytosolic 5'-nucleotidase 3
      Reactions:
      Guanosine monophosphate + Water unknown Guanosine + Phosphoric acid details
      Gene Name: NT5C3
      Uniprot ID: Q9H0P0 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cytosolic purine 5'-nucleotidase
      Reactions:
      Guanosine monophosphate + Water unknown Guanosine + Phosphoric acid details
      Gene Name: NT5C2
      Uniprot ID: P49902 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Purine nucleoside phosphorylase
      Reactions:
      Guanosine + Phosphoric acid unknown Guanine + Ribose 1-phosphate details
      Gene Name: PNP
      Uniprot ID: P00491 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA