Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

Record Information
Version	2.0
Creation Date	2012-05-31 14:50:47 -0600
Update Date	2015-06-03 17:20:18 -0600
Secondary Accession Numbers	ECMDB20562
Identification
Name:	GMP-Lysine
Description	GMP-lysine is a member of the chemical class known as Purine Ribonucleoside Monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. GMP-lysine is a nucleotidyl-modified amino acid. The hinT gene product is capable of cleaving lysine from GMP and AMP. Though specific protein targets remain to be identified, it is has been hypothesized that Hint hydrolases may reverse nucleotidylylated protein modifications of lysine. In E. coli, the Hint-homologous hinT gene is required for resistance to elevated levels of certain salts.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xabb25998> Close
Synonyms:	GMP-lysine
Chemical Formula:	C16H27N7O9P
Weight:	Average: 492.4008 Monoisotopic: 492.160787009
InChI Key:	XRYPUFFHVWYVTB-BAYCTPFLSA-P
InChI:	InChI=1S/C16H25N7O9P/c17-4-2-1-3-7(18)15(27)32-33(28,29)30-5-8-10(24)11(25)14(31-8)23-6-20-9-12(23)21-16(19)22-13(9)26/h6-8,10-11,14,24-25H,1-5,17-18H2,(H3-,19,21,22,26,28,29)/p+2/t7-,8-,10-,11-,14-/m1/s1
CAS number:	Not Available
IUPAC Name:	9-[(2R,3R,4S,5R)-5-{[({[(2R)-2,6-diazaniumylhexanoyl]oxy}(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-6-hydroxy-2-imino-3,9-dihydro-2H-7λ⁵-purin-7-ylium-3-id-7-yl
Traditional IUPAC Name:	9-[(2R,3R,4S,5R)-5-[({[(2R)-2,6-diammoniohexanoyl]oxy(hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-6-hydroxy-2-imino-3H-7λ⁵-purin-7-ylium-3-id-7-yl
SMILES:	[H][C@@]([NH3+])(CCCC[NH3+])C(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=[N+]C3=C2[N-]C(=N)N=C3O)[C@]([H])(O)[C@]1([H])O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Purine nucleotides
Sub Class	Purine ribonucleotides
Direct Parent	Purine ribonucleoside monophosphates
Alternative Parents	Pentose phosphates Glycosylamines Monosaccharide phosphates Alpha amino acids and derivatives Purines and purine derivatives Monoalkyl phosphates Hydroxypyrimidines Acyl phosphates N-substituted imidazoles Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Carboxylic acid salts 1,2-diols Oxacyclic compounds Monocarboxylic acids and derivatives Azacyclic compounds Organopnictogen compounds Organic salts Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds Organic cations
Substituents	Purine ribonucleoside monophosphate Pentose-5-phosphate Pentose phosphate N-glycosyl compound Glycosyl compound Pentose monosaccharide Monosaccharide phosphate Alpha-amino acid or derivatives Purine Imidazopyrimidine Hydroxypyrimidine Monoalkyl phosphate Acyl phosphate Alkyl phosphate Pyrimidine Phosphoric acid ester Organic phosphoric acid derivative N-substituted imidazole Monosaccharide Heteroaromatic compound Tetrahydrofuran Imidazole Azole Secondary alcohol Carboxylic acid salt Amino acid or derivatives 1,2-diol Oxacycle Azacycle Organoheterocyclic compound Monocarboxylic acid or derivatives Carboxylic acid derivative Organic nitrogen compound Organic oxygen compound Organopnictogen compound Organic oxide Hydrocarbon derivative Organic salt Primary amine Organooxygen compound Organonitrogen compound Primary aliphatic amine Carbonyl group Amine Alcohol Organic cation Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 1.17 g/L ALOGPS logP -1.5 ALOGPS logP -9.1 ChemAxon logS -2.7 ALOGPS pKa (Strongest Acidic) -0.94 ChemAxon pKa (Strongest Basic) 10.22 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 10 ChemAxon Hydrogen Donor Count 7 ChemAxon Polar Surface Area 261.29 Ų ChemAxon Rotatable Bond Count 11 ChemAxon Refractivity 160.2 m³·mol⁻¹ ChemAxon Polarizability 45.35 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:	GMP-Lysine + Water > Guanosine monophosphate + N-alpha-acetyl lysine methyl ester
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0udl-1900400000-d2adc2bc04ebfedbcf70 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0udr-5900100000-59adb316275c8ea07f5a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0uk9-9400000000-1fe770545d3d92c4dcb8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0006-1121900000-53c73be399485ba765e9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9140100000-f00a21b0fca97d6a1cf1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-003r-9110000000-26ff485d6a8c05953087 View in MoNA 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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID Not Available Pubchem Compound ID 25202936 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID GMP-LYSINE-PHOSPHORAMIDATE EcoCyc ID GMP-LYSINE-PHOSPHORAMIDATE