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Escherichia coli K-12 substr. MG1655 Compound: cyclic-AMP

Synonyms: cyclic 3',5'-AMP, 3',5'-cyclic AMP, adenosine cyclic-3',5'-monophosphate, adenosine cyclic-monophosphate, adenosine-cyclic-phosphoric-acid, cAMP, adenosine-cyclic-phosphate, adenosine-3',5'-monophosphate, adenosine 3',5'-cyclic phosphate, adenosine-3',5'-cyclic monophosphate, cyclic-3',5'-adenosine monophosphate

Superclasses: a nucleic acid component a nucleotide a cyclic nucleotide a cyclic nucleoside monophosphate a cyclic 3',5'-nucleoside monophosphate
a nucleic acid component

Component of: CRP-cAMP DNA-binding transcriptional dual regulator (extended summary available)

Chemical Formula: C10H11N5O6P

Molecular Weight: 328.2 Daltons

Monoisotopic Molecular Weight: 329.05251965379995 Daltons

SMILES: C1(OP(=O)([O-])OC2(C(O)C(OC12)N4(C=NC3(C(N)=NC=NC=34))))

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)/p-1/t4-,6-,7-,10-/m1/s1

InChIKey: InChIKey=IVOMOUWHDPKRLL-KQYNXXCUSA-M

Unification Links: CAS:60-92-4 , ChEBI:58165 , ChemSpider:5415746 , HMDB:HMDB00058 , IAF1260:1484809 , KEGG:C00575 , MetaboLights:MTBLC58165 , PubChem:7059571

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -151.279

Reactions known to consume the compound:

Not in pathways:
cyclic-AMP + H2O → AMP + H+

Reactions known to produce the compound:

Not in pathways:
ATP → cyclic-AMP + diphosphate

In Reactions of unknown directionality:

Not in pathways:
Crp + cyclic-AMP = CRP-cAMP DNA-binding transcriptional dual regulator

In Transport reactions:
cyclic-AMP[cytosol]cyclic-AMP[periplasmic space]

Enzymes inhibited by cyclic-AMP, sorted by the type of inhibition, are:

Inhibitor (Allosteric) of: malate dehydrogenase [Sanwal69, Sanwal69a]

In Growth Media: PMA phosphorus source test + cyclic-AMP

Transcription Units regulated by related protein CRP-cAMP DNA-binding transcriptional dual regulator (276 total):


References

Sanwal69: Sanwal BD, Smando R (1969). "Malic enzyme of Escherichia coli. Diversity of the effectors controlling enzyme activity." J Biol Chem 1969;244(7);1817-23. PMID: 4388614

Sanwal69a: Sanwal BD, Smando R (1969). "Malic enzyme of Escherichia coli. Possible mechanism for allosteric effects." J Biol Chem 1969;244(7);1824-30. PMID: 4388615


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 18.5 on Sat Nov 22, 2014, BIOCYC14A.