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Escherichia coli K-12 substr. MG1655 Compound: AMP

Synonyms: 5'-AMP, adenosine-monophosphate, adenylic acid, adenosine 5'-phosphate, adenosine 5'-monophosphate, adenylate, 5'-adenylic acid, 5'-adenosine monophosphate

Superclasses: a nucleic acid component
a nucleic acid componenta nucleotidea nucleoside 5'-monophosphatea ribonucleoside 5'-monophosphatea purine ribonucleoside 5'-monophosphate
a nucleic acid componenta nucleotidea purine nucleotidea purine ribonucleotidea purine ribonucleoside 5'-monophosphate
a nucleic acid componenta nucleotidea ribonucleotidea purine ribonucleotidea purine ribonucleoside 5'-monophosphate
a nucleic acid componenta nucleotidea ribonucleotidea ribonucleoside 5'-monophosphatea purine ribonucleoside 5'-monophosphate
an organic heterocyclic compoundan organic heterobicyclic compounda purinea purine nucleotidea purine ribonucleotidea purine ribonucleoside 5'-monophosphate
an organic heterocyclic compoundan organonitrogen heterocyclic compounda purinea purine nucleotidea purine ribonucleotidea purine ribonucleoside 5'-monophosphate

Chemical Formula: C10H12N5O7P

Molecular Weight: 345.21 Daltons

Monoisotopic Molecular Weight: 347.0630843401 Daltons

AMP compound structure

SMILES: C(C3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))OP([O-])([O-])=O

InChI: InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/p-2/t4-,6-,7-,10-/m1/s1


Unification Links: CAS:61-19-8, ChEBI:456215, ChemSpider:10239183, HMDB:HMDB00045, IAF1260:33534, KEGG:C00020, MetaboLights:MTBLC456215, NCI:20264, PubChem:15938965

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -257.9

Reactions known to consume the compound:

adenosine nucleotides degradation II :
AMP + H2O → adenosine + phosphate

adenosine nucleotides degradation III :
AMP + H2O → D-ribofuranose 5-phosphate + adenine

adenosine ribonucleotides de novo biosynthesis :

Not in pathways:

Not in pathways:
a ribonucleoside 5'-monophosphate + H2O → a ribonucleoside + phosphate

Not in pathways:
a nucleoside 5'-monophosphate[periplasm] + H2O[periplasm] → a nucleoside[periplasm] + phosphate[periplasm]

Reactions known to produce the compound:

1,4-dihydroxy-2-naphthoate biosynthesis :
ATP + 2-succinylbenzoate + coenzyme A → AMP + 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA + diphosphate

2-methylcitrate cycle I :
propanoate + ATP + coenzyme A → propanoyl-CoA + AMP + diphosphate

6-hydroxymethyl-dihydropterin diphosphate biosynthesis I :
6-hydroxymethyl-7,8-dihydropterin + ATP → 6-hydroxymethyl-7,8-dihydropterin diphosphate + AMP + H+

acetate conversion to acetyl-CoA :
acetate + ATP + coenzyme A → acetyl-CoA + AMP + diphosphate

adenine and adenosine salvage II :
AMP + diphosphate ← 5-phospho-α-D-ribose 1-diphosphate + adenine

adenosine ribonucleotides de novo biosynthesis :
adenylo-succinate → fumarate + AMP

biotin-carboxyl carrier protein assembly :
a [biotin-carboxyl-carrier protein monomer] + biotin + ATP → AMP + a biotinylated [BCCP monomer] + diphosphate + H+

citrate lyase activation :
[a holo citrate lyase acyl-carrier protein] + acetate + ATP → an acetyl-[holo citrate lyase acyl-carrier protein] + AMP + diphosphate

enterobactin biosynthesis :
a holo-[EntF peptidyl-carrier protein] + L-seryl-adenylate → a seryl-[EntF peptidyl-carrier protein] + AMP + H+
2,3-dihydroxybenzoyl adenylate + a holo-[EntB isochorismatase/aryl-carrier protein] → a 2,3-dihydroxybenzoyl-[EntB isochorismatase/aryl-carrier protein] + AMP + H+

fatty acid β-oxidation I :
a 2,3,4-saturated fatty acid + ATP + coenzyme A → a 2,3,4-saturated fatty acyl CoA + AMP + diphosphate

gluconeogenesis I , glycolysis I (from glucose 6-phosphate) , glycolysis II (from fructose 6-phosphate) :
pyruvate + ATP + H2O → phosphoenolpyruvate + AMP + phosphate + 2 H+

guanosine ribonucleotides de novo biosynthesis :
L-glutamine + XMP + ATP + H2O → L-glutamate + GMP + AMP + diphosphate + 2 H+

L-arginine biosynthesis I (via L-ornithine) :
L-aspartate + L-citrulline + ATP → L-arginino-succinate + AMP + diphosphate + H+

L-asparagine biosynthesis I :
L-glutamine + L-aspartate + ATP + H2O → L-glutamate + L-asparagine + AMP + diphosphate + H+

L-asparagine biosynthesis II :
L-aspartate + ammonium + ATP → L-asparagine + AMP + diphosphate + H+

L-carnitine degradation I :
L-carnitine + ATP + coenzyme A → L-carnitinyl-CoA + AMP + diphosphate

L-selenocysteine biosynthesis I (bacteria) :
selenide + ATP + H2O → selenophosphate + AMP + phosphate
a tRNAsec + L-serine + ATP + H+ → an L-seryl-[tRNAsec] + AMP + diphosphate

lipoate biosynthesis and incorporation II :
a [lipoyl-carrier protein]-L-lysine + octanoate + ATP → a [lipoyl-carrier protein] N6-octanoyl-L-lysine + AMP + diphosphate + H+

lipoate salvage I :
lipoyl-adenylate + a [lipoyl-carrier protein]-L-lysine → a [lipoyl-carrier protein]-N6-lipoyl-L-lysine + AMP + 2 H+

molybdenum cofactor biosynthesis :
molybdopterin adenine dinucleotide + molybdate + H+AMP + MoO2-molybdopterin cofactor + H2O
a carboxy-adenylated small subunit of molybdopterin synthase + an [L-cysteine desulfurase] L-cysteine persulfide + an reduced unknown electron acceptor → a thiocarboxylated small subunit of molybdopterin synthase + an [L-cysteine desulfurase]-L-cysteine + AMP + an oxidized unknown electron acceptor + H+

N6-L-threonylcarbamoyladenosine37-modified tRNA biosynthesis :
L-threonylcarbamoyladenylate + an adenine37 in tRNA → N6-L-threonylcarbamoyladenine37 in tRNA + AMP + H+

NAD biosynthesis I (from aspartate) :
ATP + nicotinate adenine dinucleotide + L-glutamine + H2O → AMP + L-glutamate + NAD+ + diphosphate + H+

In Reactions of unknown directionality:

Not in pathways:
ThiS-COAMP + L-cysteine = ThiS-COSH + L-alanine + AMP
protein chain elongation factor EF-P + (R)-β-lysine + ATP = protein chain elongation factor EF-P, β-lysyl-Lys34 + AMP + diphosphate
lipoyl-adenylate + [glycine cleavage system lipoyl-carrier protein]-L-lysine = a [glycine-cleavage complex H protein] N6-lipoyl-L-lysine + AMP + 2 H+
O-carbamoyladenylate + HypE = a HypE hydrogenase maturation protein-S-carboxamide + AMP
a [lipoyl-carrier protein]-L-lysine + ATP + (R)-lipoate = a [lipoyl-carrier protein]-N6-lipoyl-L-lysine + AMP + diphosphate + H+

Enzymes activated by AMP, sorted by the type of activation, are:

Activator (Allosteric) of: threonine dehydratase [Shizuta69], serine deaminase [Shizuta69], pyruvate kinase [Kotlarz75, Somani77] Activator (Mechanism unknown) of: glutaminase B [Prusiner76], glycogen phosphorylase [Yu88, Chen68a, Chen68], isocitrate dehydrogenase phosphatase [Nimmo84, Miller00], CTP:2,3,4-saturated L-phosphatidate cytidylyltransferase [Langley78, Comment 1]

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

Inhibitor (Competitive) of: malate:quinone oxidoreductase [Narindrasorasak79], ATP phosphoribosyltransferase [Tebar76], acetaldehyde dehydrogenase [Shone81, Comment 2], FMN reductase [Fieschi95, Comment 3], adenine phosphoribosyltransferase [HochstadtOzer71, Comment 4], amidophosphoribosyl transferase [Messenger79, Comment 5], selenide, water dikinase [Veres94, Comment 6], asparagine synthetase [Cedar69a, Comment 7] Inhibitor (Uncompetitive) of: ribose-phosphate diphosphokinase [Bower89, Willemoes97] Inhibitor (Noncompetitive) of: arginyl-tRNA synthetase [Charlier79], fructose-1,6-bisphosphatase [Babul83], FMN reductase [Fieschi95, Comment 8], thiamine monophosphate kinase Inhibitor (Allosteric) of: glucose-1-phosphate adenylyltransferase [Hill91, Gardiol90] Inhibitor (Mechanism unknown) of: riboflavin reductase [Fieschi95, Niviere99], acetyl-CoA synthetase (AMP-forming) [Barak04], NAD+ synthetase, NH3-dependent [Spencer67, Comment 9], glutamine synthetase [Woolfolk67, Bender77, Comment 10], phosphoenolpyruvate synthetase [Cooper69a, Chulavatnatol73], guanylate kinase [Oeschger66], acetaldehyde dehydrogenase [Shone81, Comment 11], isocitrate dehydrogenase kinase [Nimmo84, Miller00], ribose-5-phosphate isomerase A [Essenberg75]

This compound has been characterized as an alternative substrate of the following enzymes: 5'-nucleotidase, alkaline phosphatase

In Growth Media: PMA phosphorus source test + AMP


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Miller00: Miller SP, Chen R, Karschnia EJ, Romfo C, Dean A, LaPorte DC (2000). "Locations of the regulatory sites for isocitrate dehydrogenase kinase/phosphatase." J Biol Chem 275(2);833-9. PMID: 10625615

Narindrasorasak79: Narindrasorasak S, Goldie AH, Sanwal BD (1979). "Characteristics and regulation of a phospholipid-activated malate oxidase from Escherichia coli." J Biol Chem 1979;254(5);1540-5. PMID: 368072

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Yu88: Yu F, Jen Y, Takeuchi E, Inouye M, Nakayama H, Tagaya M, Fukui T (1988). "Alpha-glucan phosphorylase from Escherichia coli. Cloning of the gene, and purification and characterization of the protein." J Biol Chem 1988;263(27);13706-11. PMID: 3047129

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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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