Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:28 UTC
HMDB IDHMDB01397
Secondary Accession NumbersNone
Metabolite Identification
Common NameGuanosine monophosphate
DescriptionGuanosine 5'-monophosphate. A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature.
Structure
Thumb
Synonyms
  1. 5'-GMP
  2. E 626
  3. GMP
  4. Guanidine monophosphate
  5. Guanosine 5'-monophosphate
  6. Guanosine 5'-phosphate
  7. Guanosine 5'-phosphorate
  8. Guanosine 5'-phosphoric acid
  9. Guanosine monophosphate
  10. Guanosine-5'-monophosphate
  11. Guanosine-5'-phosphate
  12. Guanosine-phosphate
  13. Guanylate
  14. Guanylic acid
Chemical FormulaC10H14N5O8P
Average Molecular Weight363.2206
Monoisotopic Molecular Weight363.057998961
IUPAC Name{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
CAS Registry Number85-32-5
SMILES
NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1
InChI Identifier
InChI=1S/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1
InChI KeyRQFCJASXJCIDSX-UUOKFMHZSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPurine Nucleotides
Sub ClassPurine Ribonucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Glycosyl Compound
  • Hypoxanthine
  • Imidazole
  • Imidazopyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Purinone
  • Pyrimidine
  • Pyrimidone
  • Saccharide
  • Secondary Alcohol
Direct ParentPurine Ribonucleoside Monophosphates
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glutamate metabolism
  • Component of Purine metabolism
  • Component of Pyrimidine metabolism
  • Second messenger
ApplicationNot Available
Cellular locations
  • Extracellular
  • Mitochondria
  • Nucleus
  • Lysosome
  • Golgi apparatus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility369 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility3.56 g/LALOGPS
logP-2ALOGPS
logP-2.9ChemAxon
logS-2ALOGPS
pKa (strongest acidic)1.05ChemAxon
pKa (strongest basic)1.73ChemAxon
physiological charge-2ChemAxon
hydrogen acceptor count10ChemAxon
hydrogen donor count6ChemAxon
polar surface area201.75ChemAxon
rotatable bond count4ChemAxon
refractivity75.49ChemAxon
polarizability30.7ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
  • Nucleus
  • Lysosome
  • Golgi apparatus
Biofluid Locations
  • Blood
Tissue Location
  • Bladder
  • Epidermis
  • Heart
  • Intestine
  • Nerve Cells
  • Neuron
  • Platelet
  • Smooth Muscle
Pathways
NameSMPDB LinkKEGG Link
Glutamate MetabolismSMP00072map00250
Purine MetabolismSMP00050map00230
Transcription/TranslationSMP00019Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.0099 +/- 0.0024 uMAdult (>18 years old)MaleNormal
  • Geigy Scient...
BloodDetected and Quantified0.0095 +/- 0.0021 uMAdult (>18 years old)FemaleNormal
  • Geigy Scient...
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01972
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012390
KNApSAcK IDC00019635
Chemspider ID6545
KEGG Compound IDC00144
BioCyc IDGMP
BiGG ID34024
Wikipedia LinkGMP
NuGOwiki LinkHMDB01397
Metagene LinkHMDB01397
METLIN ID6216
PubChem Compound6804
PDB ID5GP
ChEBI ID17345
References
Synthesis ReferenceSato, Katsuaki; Matsui, Hiroshi; Ei, Hitoshi; Takinami, Koichi. Guanosine-5'-monophosphate. Jpn. Kokai Tokkyo Koho (1979), 3 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Scheen AJ: [Medication of the month. Vardenafil (Levitra)] Rev Med Liege. 2003 Sep;58(9):576-9. Pubmed: 14626653
  2. Begonja AJ, Gambaryan S, Geiger J, Aktas B, Pozgajova M, Nieswandt B, Walter U: Platelet NAD(P)H-oxidase-generated ROS production regulates alphaIIbbeta3-integrin activation independent of the NO/cGMP pathway. Blood. 2005 Oct 15;106(8):2757-60. Epub 2005 Jun 23. Pubmed: 15976180
  3. Zhao L, Gray L, Leonardi-Bee J, Weaver CS, Heptinstall S, Bath PM: Effect of aspirin, clopidogrel and dipyridamole on soluble markers of vascular function in normal volunteers and patients with prior ischaemic stroke. Platelets. 2006 Mar;17(2):100-4. Pubmed: 16421011
  4. Matata BM, Galinanes M: Effect of diabetes on nitric oxide metabolism during cardiac surgery. Diabetes. 2001 Nov;50(11):2603-10. Pubmed: 11679441
  5. Sales ME, Espanol AJ, Sterin-Borda L, Borda E, de Bracco MM: Protein kinase C regulates NO-cGMP pathway in muscarinic receptor activation by HIV+-IgA. Int J Mol Med. 1999 Jun;3(6):633-7. Pubmed: 10341295
  6. Boehning D, Moon C, Sharma S, Hurt KJ, Hester LD, Ronnett GV, Shugar D, Snyder SH: Carbon monoxide neurotransmission activated by CK2 phosphorylation of heme oxygenase-2. Neuron. 2003 Sep 25;40(1):129-37. Pubmed: 14527438
  7. Favory R, Lancel S, Tissier S, Mathieu D, Decoster B, Neviere R: Myocardial dysfunction and potential cardiac hypoxia in rats induced by carbon monoxide inhalation. Am J Respir Crit Care Med. 2006 Aug 1;174(3):320-5. Epub 2006 May 11. Pubmed: 16690979
  8. Yildiz O, Gul H, Ozgok Y, Onguru O, Kilciler M, Aydin A, Isimer A, Harmankaya AC: Increased vasoconstrictor reactivity and decreased endothelial function in high grade varicocele; functional and morphological study. Urol Res. 2003 Oct;31(5):323-8. Epub 2003 Jul 11. Pubmed: 14574537
  9. Seftel AD: Phosphodiesterase type 5 inhibitor differentiation based on selectivity, pharmacokinetic, and efficacy profiles. Clin Cardiol. 2004 Apr;27(4 Suppl 1):I14-19. Pubmed: 15115191
  10. Salomon P, Przewlocka-Kosmala M, Orda A: [Plasma levels of brain natriuretic peptide, cyclic 3'5'-guanosine monophosphate, endothelin 1, and noradrenaline in patients with chronic congestive heart failure] Pol Arch Med Wewn. 2003 Jan;109(1):43-8. Pubmed: 12879765
  11. Khush KK, De Marco T, Vakharia KT, Harmon C, Fineman JR, Chatterjee K, Michaels AD: Nesiritide acutely increases pulmonary and systemic levels of nitric oxide in patients with pulmonary hypertension. J Card Fail. 2006 Sep;12(7):507-13. Pubmed: 16952783
  12. Yoshimura N, Seki S, Chancellor MB, de Groat WC, Ueda T: Targeting afferent hyperexcitability for therapy of the painful bladder syndrome. Urology. 2002 May;59(5 Suppl 1):61-7. Pubmed: 12007524
  13. Ralph DJ: Normal erectile function. Clin Cornerstone. 2005;7(1):13-8. Pubmed: 16156419
  14. Rosen RC, McKenna KE: PDE-5 inhibition and sexual response: pharmacological mechanisms and clinical outcomes. Annu Rev Sex Res. 2002;13:36-88. Pubmed: 12836729
  15. Zusman RM, Morales A, Glasser DB, Osterloh IH: Overall cardiovascular profile of sildenafil citrate. Am J Cardiol. 1999 Mar 4;83(5A):35C-44C. Pubmed: 10078541
  16. Hamed EA, Meki AR, Gaafar AA, Hamed SA: Role of some vasoactive mediators in patients with erectile dysfunction: their relationship with angiotensin-converting enzyme and growth hormone. Int J Impot Res. 2003 Dec;15(6):418-25. Pubmed: 14671660
  17. Ehsan A, Sommer F, Schmidt A, Klotz T, Koslowski J, Niggemann S, Jacobs G, Engelmann U, Addicks K, Bloch W: Nitric oxide pathways in human bladder carcinoma. The distribution of nitric oxide synthases, soluble guanylyl cyclase, cyclic guanosine monophosphate, and nitrotyrosine. Cancer. 2002 Dec 1;95(11):2293-301. Pubmed: 12436434
  18. Lepore JJ, Maroo A, Bigatello LM, Dec GW, Zapol WM, Bloch KD, Semigran MJ: Hemodynamic effects of sildenafil in patients with congestive heart failure and pulmonary hypertension: combined administration with inhaled nitric oxide. Chest. 2005 May;127(5):1647-53. Pubmed: 15888841
  19. Kekilli M, Beyazit Y, Purnak T, Dogan S, Atalar E: Acute myocardial infarction after sildenafil citrate ingestion. Ann Pharmacother. 2005 Jul-Aug;39(7-8):1362-4. Epub 2005 May 24. Pubmed: 15914518
  20. Ivanovic Z, Duchez P, Dazey B, Hermitte F, Lamrissi-Garcia I, Mazurier F, Praloran V, Reiffers J, Vezon G, Boiron JM: A clinical-scale expansion of mobilized CD 34+ hematopoietic stem and progenitor cells by use of a new serum-free medium. Transfusion. 2006 Jan;46(1):126-31. Pubmed: 16398741

Only showing the first 50 proteins. There are 198 proteins in total.

Enzymes

Gene Name:
NT5E
Uniprot ID:
P21589
Reactions
Guanosine monophosphate + Water unknown Guanosine + Phosphoric aciddetails
Gene Name:
NT5C1B
Uniprot ID:
Q96P26
Reactions
Guanosine monophosphate + Water unknown Guanosine + Phosphoric aciddetails
Gene Name:
NT5C1A
Uniprot ID:
Q9BXI3
Reactions
Guanosine monophosphate + Water unknown Guanosine + Phosphoric aciddetails
Gene Name:
NT5C
Uniprot ID:
Q8TCD5
Reactions
Guanosine monophosphate + Water unknown Guanosine + Phosphoric aciddetails
Gene Name:
NT5M
Uniprot ID:
Q9NPB1
Reactions
Guanosine monophosphate + Water unknown Guanosine + Phosphoric aciddetails
Gene Name:
ENTPD1
Uniprot ID:
P49961
Reactions
Guanosine diphosphate + Water unknown Guanosine monophosphate + Phosphoric aciddetails
Gene Name:
CANT1
Uniprot ID:
Q8WVQ1
Reactions
Guanosine diphosphate + Water unknown Guanosine monophosphate + Phosphoric aciddetails
Gene Name:
ENTPD3
Uniprot ID:
O75355
Reactions
Guanosine diphosphate + Water unknown Guanosine monophosphate + Phosphoric aciddetails
Gene Name:
ITPA
Uniprot ID:
Q9BY32
Reactions
Guanosine triphosphate + Water unknown Guanosine monophosphate + Pyrophosphatedetails
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:
PDE6H
Uniprot ID:
Q13956
Reactions
Guanosine 3',5'-cyclic phosphate + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE1A
Uniprot ID:
P54750
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE8A
Uniprot ID:
O60658
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE1B
Uniprot ID:
Q01064
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE3B
Uniprot ID:
Q13370
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE6C
Uniprot ID:
P51160
Reactions
Guanosine 3',5'-cyclic phosphate + Water unknown Guanosine monophosphatedetails
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE7A
Uniprot ID:
Q13946
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
GMPS
Uniprot ID:
P49915
Reactions
Adenosine triphosphate + Xanthylic acid + L-Glutamine + Water unknown Adenosine monophosphate + Pyrophosphate + Guanosine monophosphate + L-Glutamic aciddetails
Adenosine triphosphate + Xanthylic acid + Ammonia unknown Adenosine monophosphate + Pyrophosphate + Guanosine monophosphatedetails
Gene Name:
PDE3A
Uniprot ID:
Q14432
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE10A
Uniprot ID:
Q9Y233
Reactions
Guanosine 3',5'-cyclic phosphate + Water unknown Guanosine monophosphatedetails
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE1C
Uniprot ID:
Q14123
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE4B
Uniprot ID:
Q07343
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE7B
Uniprot ID:
Q9NP56
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE9A
Uniprot ID:
O76083
Reactions
Guanosine 3',5'-cyclic phosphate + Water unknown Guanosine monophosphatedetails
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE2A
Uniprot ID:
O00408
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
NUDT2
Uniprot ID:
P50583
Reactions
P(1),P(4)-bis(5'-guanosyl) tetraphosphate + Water unknown Guanosine triphosphate + Guanosine monophosphatedetails
Diguanosine tetraphosphate + Water unknown Guanosine triphosphate + Guanosine monophosphatedetails
Gene Name:
PDE6A
Uniprot ID:
P16499
Reactions
Guanosine 3',5'-cyclic phosphate + Water unknown Guanosine monophosphatedetails
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE8B
Uniprot ID:
O95263
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE4C
Uniprot ID:
Q08493
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE6B
Uniprot ID:
P35913
Reactions
Guanosine 3',5'-cyclic phosphate + Water unknown Guanosine monophosphatedetails
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE4D
Uniprot ID:
Q08499
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE6G
Uniprot ID:
P18545
Reactions
Guanosine 3',5'-cyclic phosphate + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE4A
Uniprot ID:
P27815
Reactions
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
PDE5A
Uniprot ID:
O76074
Reactions
Guanosine 3',5'-cyclic phosphate + Water unknown Guanosine monophosphatedetails
Cyclic GMP + Water unknown Guanosine monophosphatedetails
Gene Name:
GMPR2
Uniprot ID:
Q9P2T1
Reactions
Inosinic acid + Ammonia + NADP unknown Guanosine monophosphate + NADPHdetails
Inosinic acid + Ammonia + NADP unknown Guanosine monophosphate + NADPH + Hydrogen Iondetails
Gene Name:
GMPR
Uniprot ID:
P36959
Reactions
Inosinic acid + Ammonia + NADP unknown Guanosine monophosphate + NADPHdetails
Inosinic acid + Ammonia + NADP unknown Guanosine monophosphate + NADPH + Hydrogen Iondetails
Gene Name:
ENTPD4
Uniprot ID:
Q9Y227
Reactions
Guanosine diphosphate + Water unknown Guanosine monophosphate + Phosphoric aciddetails
Gene Name:
ENTPD6
Uniprot ID:
O75354
Reactions
Guanosine diphosphate + Water unknown Guanosine monophosphate + Phosphoric aciddetails
Gene Name:
ENTPD5
Uniprot ID:
O75356
Reactions
Guanosine diphosphate + Water unknown Guanosine monophosphate + Phosphoric aciddetails
Gene Name:
GUK1
Uniprot ID:
Q16774
Reactions
Adenosine triphosphate + Guanosine monophosphate unknown ADP + Guanosine diphosphatedetails
Gene Name:
GUCY2C
Uniprot ID:
P25092
Gene Name:
RAPGEF2
Uniprot ID:
Q9Y4G8
Gene Name:
DLG4
Uniprot ID:
P78352

Only showing the first 50 proteins. There are 198 proteins in total.