2.0 2012-05-31 09:56:20 -0600 2015-09-13 12:56:05 -0600 ECMDB00058 M2MDB000020 Cyclic AMP 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. 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 AMP 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 monophosphoric acid Adenosine 3',5'-cyclic phosphate Adenosine 3',5'-cyclic phosphoric acid Adenosine 3',5'-cyclophosphate Adenosine 3',5'-cyclophosphoric acid Adenosine 3',5'-monophosphate Adenosine 3',5'-monophosphoric acid Adenosine 3,5'-cyclic monophosphate Adenosine 3,5'-cyclic monophosphorate Adenosine 3,5'-cyclic monophosphoric acid Adenosine cyclic monophosphate Adenosine cyclic monophosphoric acid Adenosine cyclic-3',5'-monophosphate Adenosine cyclic-3',5'-monophosphoric acid Adenosine cyclic-monophosphate Adenosine cyclic-monophosphoric acid Adenosine-3',5'-cyclic monophosphate Adenosine-3',5'-cyclic monophosphoric acid Adenosine-3',5'-monophosphate Adenosine-3',5'-monophosphoric acid Adenosine-cyclic-phosphate Adenosine-cyclic-phosphoric acid Adenosine-cyclic-phosphoric-acid CAMP Cyclic 3',5'-adenylate Cyclic 3',5'-adenylic acid Cyclic 3',5'-AMP Cyclic adenosine 3',5'-phosphate Cyclic adenosine 3',5'-phosphoric acid Cyclic AMP C10H12N5O6P 329.2059 329.052519653 (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-one 60-92-4 NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(O)(=O)O[C@H]2[C@H]1O 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 IVOMOUWHDPKRLL-KQYNXXCUSA-N Solid Cytosol logp -2.29 ALOGPS logs -1.96 ALOGPS solubility 3.58e+00 g/l ALOGPS melting_point 219-220 oC logp -3.4 ChemAxon pka_strongest_acidic 1.83 ChemAxon pka_strongest_basic 3.92 ChemAxon iupac (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 ChemAxon average_mass 329.2059 ChemAxon mono_mass 329.052519653 ChemAxon smiles NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(O)(=O)O[C@H]2[C@H]1O ChemAxon formula C10H12N5O6P ChemAxon inchi 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 ChemAxon inchikey IVOMOUWHDPKRLL-KQYNXXCUSA-N ChemAxon polar_surface_area 154.84 ChemAxon refractivity 70.29 ChemAxon polarizability 28.42 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 8 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 Lac Operon When 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. PW000955 Signaling Lac Operon Inactivation 2 When 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 operon PW000956 Signaling Specdb::CMs 306 Specdb::CMs 2241 Specdb::CMs 25821 Specdb::CMs 30850 Specdb::CMs 30976 Specdb::CMs 37271 Specdb::CMs 168998 Specdb::CMs 1049382 Specdb::CMs 1049384 Specdb::CMs 1049386 Specdb::CMs 1049388 Specdb::CMs 1049390 Specdb::NmrOneD 1059 Specdb::NmrOneD 4730 Specdb::NmrOneD 4731 Specdb::NmrOneD 141990 Specdb::NmrOneD 141991 Specdb::NmrOneD 141992 Specdb::NmrOneD 141993 Specdb::NmrOneD 141994 Specdb::NmrOneD 141995 Specdb::NmrOneD 141996 Specdb::NmrOneD 141997 Specdb::NmrOneD 141998 Specdb::NmrOneD 141999 Specdb::NmrOneD 142000 Specdb::NmrOneD 142001 Specdb::NmrOneD 142002 Specdb::NmrOneD 142003 Specdb::NmrOneD 142004 Specdb::NmrOneD 142005 Specdb::NmrOneD 142006 Specdb::NmrOneD 142007 Specdb::NmrOneD 142008 Specdb::NmrOneD 142009 Specdb::MsMs 93 Specdb::MsMs 94 Specdb::MsMs 95 Specdb::MsMs 2693 Specdb::MsMs 2694 Specdb::MsMs 2695 Specdb::MsMs 2696 Specdb::MsMs 2697 Specdb::MsMs 2698 Specdb::MsMs 2699 Specdb::MsMs 2700 Specdb::MsMs 2701 Specdb::MsMs 2702 Specdb::MsMs 2703 Specdb::MsMs 2704 Specdb::MsMs 2705 Specdb::MsMs 2706 Specdb::MsMs 2707 Specdb::MsMs 2708 Specdb::MsMs 2710 Specdb::MsMs 2711 Specdb::MsMs 2712 Specdb::MsMs 179133 Specdb::MsMs 179134 Specdb::MsMs 179135 Specdb::NmrTwoD 946 Specdb::NmrTwoD 1117 HMDB00058 6076 5851 C00575 17489 CAMP CMP Cyclic AMP Keseler, I. 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Synthesis (1989), (1), 53-4. http://hmdb.ca/system/metabolites/msds/000/000/042/original/HMDB00058.pdf?1358462082 Adenylate cyclase P00936 CYAA_ECOLI cyaA http://ecmdb.ca/proteins/P00936.xml Oxygen sensor protein DosP P76129 DOSP_ECOLI dosP http://ecmdb.ca/proteins/P76129.xml Cyclic AMP + Water > Adenosine monophosphate + Hydrogen ion RXN0-5038 Adenosine triphosphate <> Cyclic AMP + Pyrophosphate R00089 ADENYLATECYC-RXN Adenosine triphosphate > Cyclic AMP + Pyrophosphate ADENYLATECYC-RXN Cyclic AMP + Water > Adenosine monophosphate Adenosine triphosphate <> Cyclic AMP + Pyrophosphate Adenosine triphosphate <> Cyclic AMP + Pyrophosphate Gutnick 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 glucose Shake flask and filter culture 35.2 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 140800 0 Bennett, 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 Gutnick 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 glycerol Shake flask and filter culture 83.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 332000 0 Bennett, 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 Gutnick 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 acetate Shake flask and filter culture 146.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 584000 0 Bennett, 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