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Record Information
Version	2.0
Creation Date	2012-05-31 14:33:04 -0600
Update Date	2015-06-03 17:19:32 -0600
Secondary Accession Numbers	ECMDB20205
Identification
Name:	UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
Description	UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine is a member of the chemical class known as Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. UDP-MurNAc-pentapeptide is a peptidoglycan precursor. It is a key component of peptidoglycan synthesis. The peptidoglycan synthesis pathway starts at the cytoplasm, where in six steps the peptidoglycan precursor a UDP-N-acetylmuramoyl-pentapeptide is synthesized. This precursor is then attached to the memberane acceptor all-trans-undecaprenyl phosphate, generating a N-acetylmuramoyl-pentapeptide-diphosphoundecaprenol, also known as lipid I. Another transferase then adds UDP-N-acetyl-alpha-D-glucosamine, yielding the complete monomeric unit a lipid , also known as lipid . This final lipid intermediate is transferred through the membrane. The peptidoglycan monomers are then polymerized on the outside surface by glycosyltransferases, which form the linear glycan chains, and transpeptidases, which catalyze the formation of peptide crosslinks. UDP-MurNAc-pentapeptide is a feedback inhibitor of UDP-MurNAc-peptide synthesis. (PMID 357424)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa6d0e278> Close
Synonyms:	UDP-Mur2Ac(oyl-L-Ala-g-D-Glu-L-Lys-D-Ala-D-Ala) UDP-MurNAc-pentapeptide UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine UDP-N-Acetylmuramoyl-L-alanyl-g-D-glutamyl-L-lysyl-D-alanyl-D-alanine UDP-N-Acetylmuramoyl-L-alanyl-gamma-D-glutamyl-L-lysyl-D-alanyl-D-alanine UDP-N-Acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine Udpmurac(oyl-L-ala-D-g-glu-L-lys-D-ala-D-ala) Udpmurac(oyl-L-ala-D-gamma-glu-L-LYS-D-ala-D-ala) Udpmurac(oyl-L-ala-D-γ-glu-L-lys-D-ala-D-ala)
Chemical Formula:	C40H65N9O26P2
Weight:	Average: 1149.9363 Monoisotopic: 1149.351596321
InChI Key:	PFMVORMCVGOQKR-FQSOPKRZSA-N
InChI:	InChI=1S/C40H65N9O26P2/c1-16(32(57)44-18(3)37(61)62)43-35(60)21(8-6-7-12-41)46-25(52)10-9-22(38(63)64)47-33(58)17(2)42-34(59)19(4)71-31-27(45-20(5)51)39(73-23(14-50)29(31)55)74-77(68,69)75-76(66,67)70-15-24-28(54)30(56)36(72-24)49-13-11-26(53)48-40(49)65/h11,13,16-19,21-24,27-31,36,39,50,54-56H,6-10,12,14-15,41H2,1-5H3,(H,42,59)(H,43,60)(H,44,57)(H,45,51)(H,46,52)(H,47,58)(H,61,62)(H,63,64)(H,66,67)(H,68,69)(H,48,53,65)/t16-,17+,18-,19?,21+,22?,23-,24-,27-,28-,29-,30-,31-,36-,39?/m1/s1
CAS number:	Not Available
IUPAC Name:	4-{[(1S)-5-amino-1-{[(1R)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}pentyl]-C-hydroxycarbonimidoyl}-2-{[(2S)-2-[(2-{[(3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene]amino}butanoic acid
Traditional IUPAC Name:	4-{[(1S)-5-amino-1-{[(1R)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}pentyl]-C-hydroxycarbonimidoyl}-2-{[(2S)-2-[(2-{[(3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene]amino}butanoic acid
SMILES:	[H]C(C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC(O)=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(C)O)C(O)=N[C@@]([H])(C)C(O)=NC([H])(CCC(O)=N[C@@]([H])(CCCCN)C(O)=N[C@]([H])(C)C(O)=N[C@]([H])(C)C(O)=O)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Prenol lipids
Sub Class	Polyprenols
Direct Parent	Polyprenyl phospho carbohydrates
Alternative Parents	Polyterpenoids Bactoprenol diphosphates Polyprenyl monophosphates Oligopeptides Saccharolipids N-acyl-alpha-hexosamines Glutamine and derivatives Disaccharide phosphates N-acyl-alpha amino acids Alpha amino acid amides O-glycosyl compounds Alanine and derivatives Organic pyrophosphates L-alpha-amino acids Isoprenoid phosphates Medium-chain fatty acids Monoalkyl phosphates Hydroxy fatty acids Oxanes N-acyl amines Dicarboxylic acids and derivatives Acetamides Secondary carboxylic acid amides Secondary alcohols Primary carboxylic acid amides Amino acids Oxacyclic compounds Dialkyl ethers Carboxylic acids Acetals Primary alcohols Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
Substituents	Polyterpenoid Bactoprenol diphosphate Polyprenyl phospho carbohydrate Alpha-oligopeptide Polyprenyl monophosphate Polyprenyl phosphate skeleton Alpha peptide Saccharolipid Glutamine or derivatives N-acyl-alpha-hexosamine Disaccharide phosphate N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid Alpha-amino acid amide Alanine or derivatives O-glycosyl compound Glycosyl compound Disaccharide L-alpha-amino acid Organic pyrophosphate Isoprenoid phosphate Alpha-amino acid or derivatives N-substituted-alpha-amino acid Alpha-amino acid Medium-chain fatty acid Monoalkyl phosphate Hydroxy fatty acid Fatty acyl Alkyl phosphate Phosphoric acid ester Oxane Organic phosphoric acid derivative N-acyl-amine Fatty amide Dicarboxylic acid or derivatives Acetamide Amino acid Secondary carboxylic acid amide Secondary alcohol Primary carboxylic acid amide Carboxamide group Amino acid or derivatives Oxacycle Organoheterocyclic compound Ether Dialkyl ether Carboxylic acid Carboxylic acid derivative Acetal Organic nitrogen compound Organic oxygen compound Organopnictogen compound Organic oxide Hydrocarbon derivative Primary amine Primary alcohol Organooxygen compound Organonitrogen compound Primary aliphatic amine Carbonyl group Amine Alcohol Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.2 g/L ALOGPS logP -0.38 ALOGPS logP -3.7 ChemAxon logS -3.8 ALOGPS pKa (Strongest Acidic) 1.71 ChemAxon pKa (Strongest Basic) 10.21 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 31 ChemAxon Hydrogen Donor Count 16 ChemAxon Polar Surface Area 559.96 Ų ChemAxon Rotatable Bond Count 30 ChemAxon Refractivity 250.93 m³·mol⁻¹ ChemAxon Polarizability 106.12 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:	Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-gamma-D-glutamyl-L-lysine + D-Alanyl-D-alanine <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine + Di-trans,poly-cis-undecaprenyl phosphate + UDP-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala) <> Uridine 5'-monophosphate + MurAc(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala)-diphospho-undecaprenol + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-gamma-D-glutamyl-L-lysine + D-Alanyl-D-alanine > ADP + Inorganic phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
SMPDB Pathways:	Lysine biosynthesis PW000771
KEGG Pathways:	Lysine biosynthesis ec00300 Metabolic pathways eco01100 Peptidoglycan biosynthesis ec00550
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 splash10-03di-1900100000-ca60f48eab121e478fd8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03di-3900000100-5f1cabf69b348c6629aa View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03di-6921100001-9b4fc4ff9dae58b61f10 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03e9-5901100100-e2f2c32dccc7d77d95a4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001l-4903100002-39705f2f3e29d8e03294 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0bvl-4913011000-3d8817522bb28cc942c2 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:	Ishiguro, E. E., Ramey, W. D. (1978). "Involvement of the relA gene product and feedback inhibition in the regulation of DUP-N-acetylmuramyl-peptide synthesis in Escherichia coli." J Bacteriol 135:766-774. Pubmed: 357424 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 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 17277 HMDB ID Not Available Pubchem Compound ID 440448 Kegg ID C04702 ChemSpider ID 389383 Wikipedia ID Not Available BioCyc ID C3 EcoCyc ID C3

Enzymes