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Record Information
Version	2.0
Creation Date	2012-05-31 14:53:09 -0600
Update Date	2015-06-03 17:20:22 -0600
Secondary Accession Numbers	ECMDB20608
Identification
Name:	L-Seryl-AMP
Description	L-Seryl-AMP is an enzyme-bound intermediate found in the protein EntF. EntF is the enzyme responsible for serine activation during the biosynthesis of enterobactin (a cyclic trimer of N-dihydroxybenzoyl serine) in Escherichia coli. Serine adenylate is also an intermediate in the charging of Seryl-tRNA-synthetase. In particular, Mg.ATP and serine react to form seryl-adenylate on the protein. The serine is subsequently transferred to the 3'-end of the tRNA. Seryl-tRNA synthetase is also capable of synthesizing diadenosine tetraphosphate (Ap4A) from the enzyme-bound seryl-adenylate intermediate and a second molecule of ATP.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xadf27058> Close
Synonyms:	(L-Seryl)adenylate (L-Seryl)adenylic acid L-Serine adenylate L-Serine adenylic acid L-Serine AMP L-Seryl-adenylate L-Seryl-adenylic acid Serine adenylate Serine adenylic acid Serine AMP Seryl adenylate Seryl adenylic acid Seryl-AMP SRP
Chemical Formula:	C13H19N6O9P
Weight:	Average: 434.2985 Monoisotopic: 434.095112748
InChI Key:	UVSYURUCZPPUQD-MACXSXHHSA-N
InChI:	InChI=1S/C13H19N6O9P/c14-5(1-20)13(23)28-29(24,25)26-2-6-8(21)9(22)12(27-6)19-4-18-7-10(15)16-3-17-11(7)19/h3-6,8-9,12,20-22H,1-2,14H2,(H,24,25)(H2,15,16,17)/t5-,6+,8+,9+,12+/m0/s1
CAS number:	52435-67-3
IUPAC Name:	{[(2S)-2-amino-3-hydroxypropanoyl]oxy}({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid
Traditional IUPAC Name:	L-seryl-AMP
SMILES:	[H][C@](N)(CO)C(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as 5'-acylphosphoadenosines. These are ribonucleoside derivatives containing an adenoside moiety, where the phosphate group is acylated.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Purine nucleotides
Sub Class	Purine ribonucleotides
Direct Parent	5'-acylphosphoadenosines
Alternative Parents	Pentose phosphates Serine and derivatives Glycosylamines 6-aminopurines Monosaccharide phosphates Phosphoethanolamines Acyl phosphates Aminopyrimidines and derivatives Beta hydroxy acids and derivatives Monoalkyl phosphates N-substituted imidazoles Imidolactams Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Carboxylic acid salts Oxacyclic compounds Azacyclic compounds Monocarboxylic acids and derivatives Organic oxides Carbonyl compounds Organic salts Primary alcohols Organopnictogen compounds Monoalkylamines Hydrocarbon derivatives
Substituents	5'-acylphosphoadenosine Pentose phosphate Pentose-5-phosphate Serine or derivatives Glycosyl compound N-glycosyl compound 6-aminopurine Alpha-amino acid or derivatives Monosaccharide phosphate Imidazopyrimidine Purine Phosphoethanolamine Acyl phosphate Aminopyrimidine Beta-hydroxy acid Monoalkyl phosphate Pyrimidine Imidolactam Monosaccharide Phosphoric acid ester N-substituted imidazole Alkyl phosphate Organic phosphoric acid derivative Hydroxy acid Imidazole Heteroaromatic compound Azole Tetrahydrofuran Amino acid or derivatives Carboxylic acid salt Secondary alcohol Monocarboxylic acid or derivatives Oxacycle Carboxylic acid derivative Azacycle Organoheterocyclic compound Organonitrogen compound Organic salt Alcohol Organic oxygen compound Primary amine Carbonyl group Primary aliphatic amine Hydrocarbon derivative Organic oxide Organic nitrogen compound Amine Organopnictogen compound Primary alcohol Organooxygen compound Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	L-serine derivative (CHEBI:61645 ) purine ribonucleoside 5'-monophosphate (CHEBI:61645 )
Physical Properties
State:	Not Available
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 3.07 g/L ALOGPS logP -2.3 ALOGPS logP -4.6 ChemAxon logS -2.1 ALOGPS pKa (Strongest Acidic) 0.77 ChemAxon pKa (Strongest Basic) 6.83 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 12 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 238.39 Ų ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 92.62 m³·mol⁻¹ ChemAxon Polarizability 38.14 ų ChemAxon Number of Rings 3 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	3 (2,3-Dihydroxybenzoyl)adenylic acid + 3 L-Seryl-AMP >6 Adenosine monophosphate + Enterochelin +9 Hydrogen ion Adenosine triphosphate + Hydrogen ion + L-Serine <> Pyrophosphate + L-Seryl-AMP Adenosine triphosphate + L-Serine <> Pyrophosphate + L-Seryl-AMP (2,3-Dihydroxybenzoyl)adenylic acid + L-Seryl-AMP <> Hydrogen ion + Enterochelin + Adenosine monophosphate Adenosine triphosphate + L-Serine > Pyrophosphate + L-Seryl-AMP
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_15) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-9710300000-3cfe079a874c6fbca08b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-7900000000-8013312117d41dfcc35b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-5900000000-8d25b0d18e7dfa7c855b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00o0-3904400000-12b9aeba0543a4b758ff View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001i-4900000000-996f0b24784859aa0857 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-003r-9500000000-e072b2c35ed00139f040 View in MoNA MS Mass Spectrum (Electron Ionization) Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Keseler, 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. Pubmed: 21097882 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 61645 HMDB ID Not Available Pubchem Compound ID 5289403 Kegg ID Not Available ChemSpider ID 4451381 Wikipedia ID Not Available BioCyc ID SERYL-AMP EcoCyc ID SERYL-AMP Ligand Expo SRP

Enzymes