| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:07:49 -0700 |
| HMDB ID |
HMDB00058 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Cyclic AMP |
| Description |
Cyclic AMP is an adenine nucleotide containing one phosphate group which is esterified to both the 3'- and 5'-positions of the sugar moiety. It is a second messenger and a key intracellular regulator, functioning as a mediator of activity for a number of hormones, including epinephrine, glucagon, and ACTH. cAMP is synthesized from ATP by adenylate cyclase. Adenylate cyclase is located at the cell membranes. Adenylate cyclase is activated by the hormones glucagon and adrenaline and by G protein. Liver adenylate cyclase responds more strongly to glucagon, and muscle adenylate cyclase responds more strongly to adrenaline. cAMP decomposition into AMP is catalyzed by the enzyme phosphodiesterase. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 3'5'-Cyclic AMP
- 6-(6-Amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-D][1,3,2]dioxaphosphinine-2,7-diol 2-oxide
- Acrasin
- Adenosine 3',5'-cyclic monophosphate
- Adenosine 3',5'-cyclic phosphate
- Adenosine 3',5'-cyclophosphate
- Adenosine 3',5'-monophosphate
- Adenosine 3,5'-cyclic monophosphorate
- Adenosine 3,5'-cyclic monophosphoric acid
- Adenosine cyclic monophosphate
- Adenosine cyclic-monophosphate
- Adenosine-cyclic-phosphate
- Adenosine-cyclic-phosphoric-acid
- cAMP
- Cyclic 3',5'-adenylate
- Cyclic 3',5'-adenylic acid
- Cyclic 3',5'-AMP
- Cyclic adenosine 3',5'-phosphate
- Cyclic AMP
|
| Chemical Formula |
C10H12N5O6P |
| Average Molecular Weight |
329.2059 |
| Monoisotopic Molecular Weight |
329.052519653 |
| IUPAC Name |
(4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-1,3,5,2$l^{5}-furo[3,2-d][1,3,2$l^{5}]dioxaphosphinin-2-one |
| Traditional IUPAC Name |
3',5'-cyclic amp |
| CAS Registry Number |
60-92-4 |
| SMILES |
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(O)(=O)O[C@H]2[C@H]1O |
| InChI Identifier |
InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1 |
| InChI Key |
IVOMOUWHDPKRLL-KQYNXXCUSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Nucleosides, Nucleotides, and Analogues |
| Class |
Purine Nucleotides |
| Sub Class |
Cyclic Purine Nucleotides |
| Other Descriptors |
- 3',5'-Cyclic nuclcleotides(KEGG)
- 3',5'-cyclic purine nucleotide(ChEBI)
- Aromatic Heteropolycyclic Compounds
|
| Substituents |
- 1 Phosphoribosyl Imidazole
- Aminopyrimidine
- Imidazole
- Imidazopyrimidine
- Organic Hypophosphite
- Organic Phosphite
- Oxolane
- Phosphoric Acid Ester
- Purine
- Pyrimidine
- Secondary Alcohol
|
| Direct Parent |
3',5'-cyclic Purine Nucleotides |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Component of Purine metabolism
- Second messenger
|
| Application |
Not Available |
| Cellular locations |
- Cytoplasm
- Extracellular
- Golgi apparatus
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
219 - 220 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
4 mg/mL |
Not Available |
| LogP |
-2.96 |
HANSCH,C ET AL. (1995) |
|
| Predicted Properties |
|
| Spectra |
|---|
|
| Gas-MS Spectrum |
| 1H 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 |
- Cytoplasm
- Extracellular
- Golgi apparatus
|
| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
- Urine
|
| Tissue Location |
|
| Pathways |
|
| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
0.0085 +/- 0.0005 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.020 +/- 0.004 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.020+/- 0.004 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.024 (0.022-0.026) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.021 +/- 0.008 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.020 (0.016-0.024) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.38 +/- 0.14 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.22 +/- 0.055 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
0.0077 +/- 0.0003 uM |
Adult (>18 years old) |
Male |
Sildenafil-induced headache |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.0110 +/- 0.0028 uM |
Adult (>18 years old) |
Both |
Idiopathic polyneuritis |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.033 +/- 0.012 uM |
Adult (>18 years old) |
Not Specified |
Meningitis |
Serious case.
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.00860 (0.00620-0.0110) uM |
Adult (>18 years old) |
Both |
Hypoxic-ischemic encephalopathy |
Moderate to severe Hypoxic-ischemic...
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.014 (0.012-0.017) uM |
Adult (>18 years old) |
Both |
Hypoxic-ischemic encephalopathy |
Mild Hypoxic-ischemic encephalopathy
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.0202 +/- 0.004 uM |
Adult (>18 years old) |
Not Specified |
Initial slight suspicion of meningitis with normal CSF |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.034 (0.021-0.046) uM |
Adult (>18 years old) |
Both |
Meningitis |
serious meningitis
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.011 (0.0082-0.014) uM |
Adult (>18 years old) |
Both |
Idiopathic polyneuritis |
Not Available |
| Urine |
Detected and Quantified |
|
0.24 +/- 0.028 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Chronic renal failure |
Not Available |
|
| Associated Disorders and Diseases |
|---|
| Disease References |
| Idiopathic polyneuritis |
|---|
- Lerche A, Svenson M, Wiik A: Cerebrospinal fluid levels of cyclic nucleotides in meningitis and idiopathic polyneuritis. Acta Neurol Scand. 1984 Mar;69(3):168-75.
Pubmed: 6326460
|
| Hypoxic-ischemic encephalopathy |
|---|
- Liu H, Chang L, Chen Y, Xia S, Zhang X: Clinical implication of the changes of cAMP, TXA2 and PGI2 in CSF of asphyxiated newborns. J Huazhong Univ Sci Technolog Med Sci. 2003;23(2):195-7, 200.
Pubmed: 12973949
|
| Meningitis |
|---|
- Lerche A, Svenson M, Wiik A: Cerebrospinal fluid levels of cyclic nucleotides in meningitis and idiopathic polyneuritis. Acta Neurol Scand. 1984 Mar;69(3):168-75.
Pubmed: 6326460
|
| Headache |
|---|
- Kruuse C, Frandsen E, Schifter S, Thomsen LL, Birk S, Olesen J: Plasma levels of cAMP, cGMP and CGRP in sildenafil-induced headache. Cephalalgia. 2004 Jul;24(7):547-53.
Pubmed: 15196297
|
| Chronic renal failure |
|---|
- Dimitrakov D, Kumchev E, Lyutakova E, Ledzhev I, Nikolov D, Tsekov V: Cyclic adenosine monophosphate (cAMP) levels in predialysis patients with chronic renal failure. Folia Med (Plovdiv). 1997;39(1):29-33.
Pubmed: 9141788
|
|
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
DB02527 |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB001497 |
| KNApSAcK ID |
C00001497 |
| Chemspider ID |
5851 |
| KEGG Compound ID |
C00575 |
| BioCyc ID |
CAMP |
| BiGG ID |
1484809 |
| Wikipedia Link |
Cyclic AMP |
| NuGOwiki Link |
HMDB00058 |
| Metagene Link |
HMDB00058 |
| METLIN ID |
5120 |
| PubChem Compound |
6076 |
| PDB ID |
CMP |
| ChEBI ID |
17489 |
| References |
|---|
| Synthesis Reference |
Genieser, H. G.; Butt, E.; Bottin, U.; Dostmann, W.; Jastorff, B. Synthesis of the 3',5'-cyclic phosphates from unprotected nucleosides. Synthesis (1989), (1), 53-4. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Imashuku S, Todo S, Nakajima F: [Intra-aortic prostaglandin E1 infusion in the treatment of advanced neuroblastoma] Gan To Kagaku Ryoho. 1983 Sep;10(9):1936-43.
Pubmed: 6311112
- Wine JJ, Joo NS: Submucosal glands and airway defense. Proc Am Thorac Soc. 2004;1(1):47-53.
Pubmed: 16113412
- Onali P, Strada SJ, Chang L, Epstein PM, Hersh EM, Thompson WJ: Purification and characterization of high-affinity cyclic adenosine 5'-monophosphate phosphodiesterases from human acute myelogenous leukemic cells. Cancer Res. 1985 Mar;45(3):1384-91.
Pubmed: 2982489
- Rademaker MT, Charles CJ, Lewis LK, Yandle TG, Cooper GJ, Coy DH, Richards AM, Nicholls MG: Beneficial hemodynamic and renal effects of adrenomedullin in an ovine model of heart failure. Circulation. 1997 Sep 16;96(6):1983-90.
Pubmed: 9323090
- Mashayekhi F, Aghahoseini F, Rezaie A, Zamani MJ, Khorasani R, Abdollahi M: Alteration of cyclic nucleotides levels and oxidative stress in saliva of human subjects with periodontitis. J Contemp Dent Pract. 2005 Nov 15;6(4):46-53.
Pubmed: 16299606
- Sugo T, Tachimoto H, Chikatsu T, Murakami Y, Kikukawa Y, Sato S, Kikuchi K, Nagi T, Harada M, Ogi K, Ebisawa M, Mori M: Identification of a lysophosphatidylserine receptor on mast cells. Biochem Biophys Res Commun. 2006 Mar 24;341(4):1078-87. Epub 2006 Jan 25.
Pubmed: 16460680
- Watanabe K, Beinborn M, Nagamatsu S, Ishida H, Takahashi S: Menetrier's disease in a patient with Helicobacter pylori infection is linked to elevated glucagon-like peptide-2 activity. Scand J Gastroenterol. 2005 Apr;40(4):477-81.
Pubmed: 16028444
- Naef A, Keller HU: A short transient increase in cyclic adenosine 3', 5'-monophosphate levels of neutrophil granulocytes following exposure to chemotactic factors. Adv Exp Med Biol. 1982;141:39-48.
Pubmed: 6283833
- Kukreja SC, Shevrin DH, Wimbiscus SA, Ebeling PR, Danks JA, Rodda CP, Wood WI, Martin TJ: Antibodies to parathyroid hormone-related protein lower serum calcium in athymic mouse models of malignancy-associated hypercalcemia due to human tumors. J Clin Invest. 1988 Nov;82(5):1798-802.
Pubmed: 2846659
- Wickenheisser JK, Nelson-DeGrave VL, McAllister JM: Human ovarian theca cells in culture. Trends Endocrinol Metab. 2006 Mar;17(2):65-71. Epub 2006 Feb 7.
Pubmed: 16460956
- Fouassier L, Chinet T, Robert B, Carayon A, Balladur P, Mergey M, Paul A, Poupon R, Capeau J, Barbu V, Housset C: Endothelin-1 is synthesized and inhibits cyclic adenosine monophosphate- dependent anion secretion by an autocrine/paracrine mechanism in gallbladder epithelial cells. J Clin Invest. 1998 Jun 15;101(12):2881-8.
Pubmed: 9637723
- Carceles MD, Ribo AR, Davalos R, Martinez T, Hernandez J: Effect of diazepam on adenosine 3',5'-cyclic monophosphate (cAMP) plasma levels in anesthetized patients. Clin Ther. 2004 May;26(5):737-43.
Pubmed: 15220017
- Chu MS, Chang CF, Yang CC, Bau YC, Ho LL, Hung SC: Signalling pathway in the induction of neurite outgrowth in human mesenchymal stem cells. Cell Signal. 2006 Apr;18(4):519-30. Epub 2005 Aug 11.
Pubmed: 16098715
- Rudman D, O'Brien MS, McKinney AS, Hoffman JC Jr, Patterson JH: Observations on the cyclic nucleotide concentrations in human cerebrospinal fluid. J Clin Endocrinol Metab. 1976 Jun;42(6):1088-97.
Pubmed: 180045
- Machen TE: Innate immune response in CF airway epithelia: hyperinflammatory? Am J Physiol Cell Physiol. 2006 Aug;291(2):C218-30.
Pubmed: 16825601
- Lerche A, Svenson M, Wiik A: Cerebrospinal fluid levels of cyclic nucleotides in meningitis and idiopathic polyneuritis. Acta Neurol Scand. 1984 Mar;69(3):168-75.
Pubmed: 6326460
- Ruppert D, Weithmann KU: HL 725, an extremely potent inhibitor of platelet phosphodiesterase and induced platelet aggregation in vitro. Life Sci. 1982 Nov 8;31(19):2037-43.
Pubmed: 6294426
- Tanaka Y, Horinouchi T, Koike K: New insights into beta-adrenoceptors in smooth muscle: distribution of receptor subtypes and molecular mechanisms triggering muscle relaxation. Clin Exp Pharmacol Physiol. 2005 Jul;32(7):503-14.
Pubmed: 16026507
- Fischer JA, Bourne HR, Dambacher MA, Tschopp F, De Meyer R, Devogelaer JP, Werder EA, Nagant De Deuxchaisnes C: Pseudohypoparathyroidism: inheritance and expression of deficient receptor-cyclase coupling protein activity. Clin Endocrinol (Oxf). 1983 Dec;19(6):747-54.
Pubmed: 6317236
- Liu H, Chang L, Chen Y, Xia S, Zhang X: Clinical implication of the changes of cAMP, TXA2 and PGI2 in CSF of asphyxiated newborns. J Huazhong Univ Sci Technolog Med Sci. 2003;23(2):195-7, 200.
Pubmed: 12973949
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| Enzymes |
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| Name: |
Hormone-sensitive lipase
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| Reactions: |
- (1) diacylglycerol + H2O = monoacylglycerol + a carboxylate [RN:R05209]
- (2) triacylglycerol + H2O = diacylglycerol + a carboxylate [RN:R01369]
- (3) monoacylglycerol + H2O = glycerol + a carboxylate [RN:R07293]
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| Gene Name: |
LIPE |
| Uniprot ID: |
Q05469 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
ADM2
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| Reactions: |
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| Gene Name: |
ADM2 |
| Uniprot ID: |
Q7Z4H4 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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