2.02012-05-31 09:56:20 -06002015-09-13 12:56:05 -0600ECMDB00058M2MDB000020Cyclic AMPCyclic 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. cAMP is synthesized from ATP by adenylate cyclase. Adenylate cyclase is located at the cell membranes. cAMP decomposition into AMP is catalyzed by the enzyme phosphodiesterase.3',5'-Cyclic AMP3'5'-Cyclic AMP6-(6-Amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-D][1,3,2]dioxaphosphinine-2,7-diol 2-oxideAcrasinAdenosine 3',5'-cyclic monophosphateAdenosine 3',5'-cyclic monophosphoric acidAdenosine 3',5'-cyclic phosphateAdenosine 3',5'-cyclic phosphoric acidAdenosine 3',5'-cyclophosphateAdenosine 3',5'-cyclophosphoric acidAdenosine 3',5'-monophosphateAdenosine 3',5'-monophosphoric acidAdenosine 3,5'-cyclic monophosphateAdenosine 3,5'-cyclic monophosphorateAdenosine 3,5'-cyclic monophosphoric acidAdenosine cyclic monophosphateAdenosine cyclic monophosphoric acidAdenosine cyclic-3',5'-monophosphateAdenosine cyclic-3',5'-monophosphoric acidAdenosine cyclic-monophosphateAdenosine cyclic-monophosphoric acidAdenosine-3',5'-cyclic monophosphateAdenosine-3',5'-cyclic monophosphoric acidAdenosine-3',5'-monophosphateAdenosine-3',5'-monophosphoric acidAdenosine-cyclic-phosphateAdenosine-cyclic-phosphoric acidAdenosine-cyclic-phosphoric-acidCAMPCyclic 3',5'-adenylateCyclic 3',5'-adenylic acidCyclic 3',5'-AMPCyclic adenosine 3',5'-phosphateCyclic adenosine 3',5'-phosphoric acidCyclic AMPC10H12N5O6P329.2059329.052519653(4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2,7-dihydroxy-tetrahydro-4H-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one60-92-4NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(O)(=O)O[C@H]2[C@H]1OInChI=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/s1IVOMOUWHDPKRLL-KQYNXXCUSA-NSolidCytosollogp-2.29logs-1.96solubility3.58e+00 g/lmelting_point219-220 oClogp-3.4pka_strongest_acidic1.83pka_strongest_basic3.92iupac(4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-oneaverage_mass329.2059mono_mass329.052519653smilesNC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(O)(=O)O[C@H]2[C@H]1OformulaC10H12N5O6PinchiInChI=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/s1inchikeyIVOMOUWHDPKRLL-KQYNXXCUSA-Npolar_surface_area154.84refractivity70.29polarizability28.42rotatable_bond_count1acceptor_count8donor_count3physiological_charge-1formal_charge0Purine metabolismec00230Lac OperonWhen glucose is absent and lactose is present in the environment, cyclic AMP is present and binds to the catabolite activator protein (CAP) which in turn binds to the activator binding site and facilitates transcription.
Lactose binds to the repressor and prevents it from binding to the operator site.
RNA polymerase can now bind to the promoter and carry out transcription of the lac operon.
PW000955SignalingLac Operon Inactivation 2When neither glucose nor lactose is present in the media cell, the concentration of cyclic AMP is high and the catabolite activator protein is bound to the activator binding site, But even though RNA polymerase can bind to the promoter, it is blocked by the repressor on the operator site. Hence there is no transcription of the lac operonPW000956SignalingSpecdb::CMs306Specdb::CMs2241Specdb::CMs25821Specdb::CMs30850Specdb::CMs30976Specdb::CMs37271Specdb::CMs168998Specdb::CMs1049382Specdb::CMs1049384Specdb::CMs1049386Specdb::CMs1049388Specdb::CMs1049390Specdb::NmrOneD1059Specdb::NmrOneD4730Specdb::NmrOneD4731Specdb::NmrOneD141990Specdb::NmrOneD141991Specdb::NmrOneD141992Specdb::NmrOneD141993Specdb::NmrOneD141994Specdb::NmrOneD141995Specdb::NmrOneD141996Specdb::NmrOneD141997Specdb::NmrOneD141998Specdb::NmrOneD141999Specdb::NmrOneD142000Specdb::NmrOneD142001Specdb::NmrOneD142002Specdb::NmrOneD142003Specdb::NmrOneD142004Specdb::NmrOneD142005Specdb::NmrOneD142006Specdb::NmrOneD142007Specdb::NmrOneD142008Specdb::NmrOneD142009Specdb::MsMs93Specdb::MsMs94Specdb::MsMs95Specdb::MsMs2693Specdb::MsMs2694Specdb::MsMs2695Specdb::MsMs2696Specdb::MsMs2697Specdb::MsMs2698Specdb::MsMs2699Specdb::MsMs2700Specdb::MsMs2701Specdb::MsMs2702Specdb::MsMs2703Specdb::MsMs2704Specdb::MsMs2705Specdb::MsMs2706Specdb::MsMs2707Specdb::MsMs2708Specdb::MsMs2710Specdb::MsMs2711Specdb::MsMs2712Specdb::MsMs179133Specdb::MsMs179134Specdb::MsMs179135Specdb::NmrTwoD946Specdb::NmrTwoD1117HMDB0005860765851C0057517489CAMPCMPCyclic AMPKeseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.19561621Imashuku S, Todo S, Nakajima F: [Intra-aortic prostaglandin E1 infusion in the treatment of advanced neuroblastoma] Gan To Kagaku Ryoho. 1983 Sep;10(9):1936-43.6311112Wine JJ, Joo NS: Submucosal glands and airway defense. Proc Am Thorac Soc. 2004;1(1):47-53.16113412Onali 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):1384-91.2982489Rademaker 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):1983-90.9323090Mashayekhi 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):46-53.16299606Sugo 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 25.16460680Watanabe 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):477-81.16028444Naef 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;141:39-48.6283833Kukreja 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):1798-802.2846659Wickenheisser JK, Nelson-DeGrave VL, McAllister JM: Human ovarian theca cells in culture. Trends Endocrinol Metab. 2006 Mar;17(2):65-71. Epub 2006 Feb 7.16460956Fouassier 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):2881-8.9637723Carceles 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):737-43.15220017Chu 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 11.16098715Rudman 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):1088-97.180045Machen TE: Innate immune response in CF airway epithelia: hyperinflammatory? Am J Physiol Cell Physiol. 2006 Aug;291(2):C218-30.16825601Lerche A, Svenson M, Wiik A: Cerebrospinal fluid levels of cyclic nucleotides in meningitis and idiopathic polyneuritis. Acta Neurol Scand. 1984 Mar;69(3):168-75.6326460Ruppert 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):2037-43.6294426Tanaka 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):503-14.16026507Fischer 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):747-54.6317236Liu 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, 200.12973949Genieser, 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.http://hmdb.ca/system/metabolites/msds/000/000/042/original/HMDB00058.pdf?1358462082Adenylate cyclaseP00936CYAA_ECOLIcyaAhttp://ecmdb.ca/proteins/P00936.xmlOxygen sensor protein DosPP76129DOSP_ECOLIdosPhttp://ecmdb.ca/proteins/P76129.xmlCyclic AMP + Water > Adenosine monophosphate + Hydrogen ionRXN0-5038Adenosine triphosphate <> Cyclic AMP + PyrophosphateR00089ADENYLATECYC-RXNAdenosine triphosphate > Cyclic AMP + PyrophosphateADENYLATECYC-RXNCyclic AMP + Water > Adenosine monophosphateAdenosine triphosphate <> Cyclic AMP + PyrophosphateAdenosine triphosphate <> Cyclic AMP + PyrophosphateGutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseShake flask and filter culture35.2uM0.037 oCK12 NCM3722Mid-Log Phase1408000Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.19561621Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolShake flask and filter culture83.0uM0.037 oCK12 NCM3722Mid-Log Phase3320000Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.19561621Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateShake flask and filter culture146.0uM0.037 oCK12 NCM3722Mid-Log Phase5840000Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.19561621