| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:10:28 -0700 |
| HMDB ID |
HMDB01397 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
Guanosine monophosphate |
| Description |
Guanosine 5'-monophosphate. A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 5'-GMP
- E 626
- GMP
- Guanidine monophosphate
- Guanosine 5'-monophosphate
- Guanosine 5'-phosphate
- Guanosine 5'-phosphorate
- Guanosine 5'-phosphoric acid
- Guanosine monophosphate
- Guanosine-5'-monophosphate
- Guanosine-5'-phosphate
- Guanosine-phosphate
- Guanylate
- Guanylic acid
|
| Chemical Formula |
C10H14N5O8P |
| Average Molecular Weight |
363.2206 |
| Monoisotopic Molecular Weight |
363.057998961 |
| 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 Number |
85-32-5 |
| 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 Key |
RQFCJASXJCIDSX-UUOKFMHZSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Nucleosides, Nucleotides, and Analogues |
| Class |
Purine Nucleotides |
| Sub Class |
Purine 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 Parent |
Purine Ribonucleoside Monophosphates |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Component of Glutamate metabolism
- Component of Purine metabolism
- Component of Pyrimidine metabolism
- Second messenger
|
| Application |
Not Available |
| Cellular locations |
- Extracellular
- Mitochondria
- Nucleus
- Lysosome
- Golgi apparatus
|
| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
369 mg/mL |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|
|
| Biological Properties |
| Cellular Locations |
- Extracellular
- Mitochondria
- Nucleus
- Lysosome
- Golgi apparatus
|
| Biofluid Locations |
|
| Tissue Location |
- Bladder
- Intestine
- Neuron
- Epidermis
- Nerve Cells
- Platelet
- Heart
- Smooth Muscle
|
| Pathways |
|
| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
0.0099 +/- 0.0024 uM |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
0.0095 +/- 0.0021 uM |
Adult (>18 years old) |
Female |
Normal |
Not Available |
|
| Abnormal Concentrations |
|
Not Available |
| Associated Disorders and Diseases |
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
| DrugBank ID |
DB01972  |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB012390 |
| KNApSAcK ID |
C00019635  |
| Chemspider ID |
6545  |
| KEGG Compound ID |
C00144  |
| BioCyc ID |
GMP  |
| BiGG ID |
34024  |
| Wikipedia Link |
GMP  |
| NuGOwiki Link |
HMDB01397  |
| Metagene Link |
HMDB01397  |
| METLIN ID |
6216  |
| PubChem Compound |
6804  |
| PDB ID |
5GP  |
| ChEBI ID |
17345  |
| References |
| Synthesis Reference |
Sato, 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 |
- Matata BM, Galinanes M: Effect of diabetes on nitric oxide metabolism during cardiac surgery. Diabetes. 2001 Nov;50(11):2603-10.
Pubmed: 11679441
- 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
- Scheen AJ: [Medication of the month. Vardenafil (Levitra)] Rev Med Liege. 2003 Sep;58(9):576-9.
Pubmed: 14626653
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Ralph DJ: Normal erectile function. Clin Cornerstone. 2005;7(1):13-8.
Pubmed: 16156419
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
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| Name: |
GMP reductase 2
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| Reactions: |
- inosine 5'-phosphate + NH3 + NADP+ = guanosine 5'-phosphate + NADPH + H+ [RN:R01134]
|
| Gene Name: |
GMPR2 |
| Uniprot ID: |
Q9P2T1  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
GMP reductase 1
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| Reactions: |
- inosine 5'-phosphate + NH3 + NADP+ = guanosine 5'-phosphate + NADPH + H+ [RN:R01134]
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| Gene Name: |
GMPR |
| Uniprot ID: |
P36959  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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