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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-01-11 19:15:56 UTC
HMDB IDHMDB0001397
Secondary Accession Numbers
  • HMDB01397
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
Data?1547234156
Synonyms
ValueSource
5'-GMPChEBI
GMPChEBI
Guanosine 5'-phosphateChEBI
Guanosine-5'-monophosphateChEBI
Guanylic acidChEBI
pGChEBI
Guanosine 5'-monophosphateKegg
Guanosine 5'-phosphoric acidGenerator
Guanosine-5'-monophosphoric acidGenerator
GuanylateGenerator
Guanosine 5'-monophosphoric acidGenerator
Guanosine monophosphoric acidGenerator
e 626HMDB
Guanidine monophosphateHMDB
Guanosine 5'-phosphorateHMDB
Guanosine-5'-phosphateHMDB
Guanosine-phosphateHMDB
5' Guanylic acidHMDB
Acid, 5'-guanylicHMDB
Acid, guanylicHMDB
Guanosine 5' monophosphateHMDB
5'-monoPhosphate, guanosineHMDB
monoPhosphate, guanosineHMDB
5'-Guanylic acidMeSH
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 Nameguanylate
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
Description belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Cyclopentanol
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Area201.75 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity75.49 m³·mol⁻¹ChemAxon
Polarizability30.7 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-014i-1942000000-27fc2e135f86071ba4d7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1942000000-27fc2e135f86071ba4d7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0941000000-245c5258141d8d2a9fa5JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9722000000-9155df338c7516c297b6JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ot-9522200000-3e2591b21841c753ec13JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0901000000-fbce35f7dfa73ab5fc11JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0900000000-764722cc1b8cc2aaa480JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-0900000000-c268cdce8dfd6c39fa3cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03di-0409000000-309e438ad8b6162df850JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0udi-0904000000-cf72d0459316801b014eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-abc7bfe7620db1c34775JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-01t9-9114000000-9a1071a2e17ea3ca268cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-01t9-9113000000-05a8989070e3b89138f1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01t9-9114000000-9a1071a2e17ea3ca268cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01t9-9113000000-05a8989070e3b89138f1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0409000000-309e438ad8b6162df850JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0904000000-cf72d0459316801b014eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-abc7bfe7620db1c34775JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0913000000-05cd931f142e4b624c8bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-318d089a94a5bcfd20f2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-e616291ba80c4abf405cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0imi-7709000000-6c811759b6f078f642a2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-9800000000-59c4ae8bf5bfa0d23da1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-73f60c52b80206170819JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
  • Nucleus
  • Lysosome
  • Golgi apparatus
Biospecimen Locations
  • Blood
  • Saliva
Tissue Locations
  • Bladder
  • Epidermis
  • Heart
  • Intestine
  • Nerve Cells
  • Neuron
  • Platelet
  • Smooth Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0099 +/- 0.0024 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.0095 +/- 0.0021 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
SalivaDetected and Quantified0.0898 +/- 0.212 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.199 +/- 0.245 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.262 +/- 0.501 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.312 +/- 0.229 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01972
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012390
KNApSAcK IDC00019635
Chemspider ID6545
KEGG Compound IDC00144
BioCyc IDGMP
BiGG ID34024
Wikipedia LinkGuanosine_monophosphate
METLIN ID6216
PubChem Compound6804
PDB IDNot Available
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)Download (PDF)
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 10 proteins. There are 198 proteins in total.

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 hydrolase activity
Specific function:
In the nervous system, could hydrolyze ATP and other nucleotides to regulate purinergic neurotransmission. Could also be implicated in the prevention of platelet aggregation by hydrolyzing platelet-activating ADP to AMP. Hydrolyzes ATP and ADP equally well.
Gene Name:
ENTPD1
Uniprot ID:
P49961
Molecular weight:
58706.0
Reactions
Guanosine diphosphate + Water → Guanosine monophosphate + Phosphoric aciddetails
General function:
Involved in calcium ion binding
Specific function:
Calcium-dependent nucleotidase with a preference for UDP. The order of activity with different substrates is UDP > GDP > UTP > GTP. Has very low activity towards ADP and even lower activity towards ATP. Does not hydrolyze AMP and GMP. Involved in proteoglycan synthesis.
Gene Name:
CANT1
Uniprot ID:
Q8WVQ1
Molecular weight:
44839.24
Reactions
Guanosine diphosphate + Water → Guanosine monophosphate + Phosphoric aciddetails
General function:
Involved in hydrolase activity
Specific function:
Has a threefold preference for the hydrolysis of ATP over ADP.
Gene Name:
ENTPD3
Uniprot ID:
O75355
Molecular weight:
59104.76
Reactions
Guanosine diphosphate + Water → Guanosine monophosphate + Phosphoric aciddetails
General function:
Involved in hydrolase activity
Specific function:
Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) and xanthosine 5'-triphosphate (XTP) to their respective monophosphate derivatives. The enzyme does not distinguish between the deoxy- and ribose forms. Probably excludes non-canonical purines from RNA and DNA precursor pools, thus preventing their incorporation into RNA and DNA and avoiding chromosomal lesions.
Gene Name:
ITPA
Uniprot ID:
Q9BY32
Molecular weight:
16833.23
Reactions
Guanosine triphosphate + Water → Guanosine monophosphate + Pyrophosphatedetails
General function:
Involved in adenine phosphoribosyltransferase activity
Specific function:
Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis.
Gene Name:
APRT
Uniprot ID:
P07741
Molecular weight:
19607.535
Reactions
Guanosine monophosphate + Pyrophosphate → Guanine + Phosphoribosyl pyrophosphatedetails

Only showing the first 10 proteins. There are 198 proteins in total.