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Human Metabolome Database Version 3.5

Showing metabocard for Guanosine (HMDB00133)

• Identification
• Taxonomy
• Ontology
• Physical properties
• Spectra
• Biological properties
• Concentrations
• Links
• References

enzymes (8)

• Blood
• Urine

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 ).
Structure	Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure
Synonyms	2-Amino-1,9-dihydro-9-b-D-ribofuranosyl-6H-purin-6-one 2-Amino-1,9-dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one 2-Amino-Inosine 9-b-D-Ribofuranosyl-Guanine 9-beta-delta-Ribofuranosyl-Guanine b-D-Ribofuranoside guanine-9 beta-delta-Ribofuranoside guanine-9 Guanosine Ribonucleoside 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
Normal Concentrations
	Biofluid Status Value Age Sex Condition Reference Blood Detected and Quantified 0.8 +/- 0.5 uM Adult (>18 years old) Both Normal 546939 Cellular Cytoplasm Detected and Quantified 4.5 +/- 2.9 uM Adult (>18 years old) Both Normal 7877593 Urine Detected and Quantified 0.13 (0.022-0.23) umol/mmol creatinine Adult (>18 years old) Both Normal 15116424 Urine Detected and Quantified 0.06 +/- 0.02 umol/mmol creatinine Adult (>18 years old) Female Normal 9129323 Urine Detected and Quantified 0.05 +/- 0.02 umol/mmol creatinine Adult (>18 years old) Both Normal 9129323 Urine Detected and Quantified 0.06 +/- 0.02 umol/mmol creatinine Adult (>18 years old) Both Normal 9129323
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. 10102915 Urine Detected and Quantified 35-588 umol/mmol creatinine Adult (>18 years old) Both Purine-nucleoside phosphorylase deficiency 10102915
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
Associated OMIM IDs	164050 (Purine nucleoside phosphorylase deficiency )
External Links
DrugBank ID	DB02857
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
KEGG Compound ID	C00387
BioCyc ID	GUANOSINE
BiGG ID	51567
Wikipedia Link	Guanosine
NuGOwiki Link	HMDB00133
Metagene Link	HMDB00133
METLIN ID	87
PubChem Compound	6802
PDB ID	GMP
ChEBI ID	16750
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	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 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 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 Traut TW: Physiological concentrations of purines and pyrimidines. Mol Cell Biochem. 1994 Nov 9;140(1):1-22. Pubmed: 7877593 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 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

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Enzymes
Name: 5'-nucleotidase Reactions: Guanosine monophosphate + Water unknown Guanosine + Phosphoric acid details Gene Name: NT5E Uniprot ID: P21589 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 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 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 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 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 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 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 Protein Sequence: FASTA Gene Sequence: FASTA

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