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Record Information
Version	2.0
Creation Date	2012-05-31 14:07:09 -0600
Update Date	2015-06-03 15:54:49 -0600
Secondary Accession Numbers	ECMDB04168
Identification
Name:	UDP-N-Acetylmuramoyl-L-alanine
Description	Udp-n-acetylmuramoyl-l-alanine belongs to the class of Pyrimidine Nucleotide Sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. (inferred from compound structure)UDP-N-acetylmuramoyl-L-alanine (UDP-MurNAc-L-Ala), which is the nucleotide substrate of the D-glutamic-acid-adding enzyme (the murD gene product) catalyzing the subsequent step in the pathway for peptidoglycan synthesis, appears to be an effector of the racemase activity. (PMID 8098327) MurD (UDP-N-acetylmuramoyl-L-alanine:D-glutamate ligase) is the second enzyme in the series of Mur ligases, and it catalyzes the addition of D-glutamic acid (D-Glu) to the cytoplasmic intermediate UDP-N-acetylmuramoyl-L-alanine (UMA). (PMID 19007109)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xab8c9c58> Close
Synonyms:	UDP-N-acetylmuramoyl-L-alanine UDP-MurNAcAla
Chemical Formula:	C23H36N4O20P2
Weight:	Average: 750.4943 Monoisotopic: 750.139812636
InChI Key:	NTMMCWJNQNKACG-CPDMUANVSA-N
InChI:	InChI=1S/C23H36N4O20P2/c1-8(21(35)36)24-19(34)9(2)43-18-14(25-10(3)29)22(45-11(6-28)16(18)32)46-49(40,41)47-48(38,39)42-7-12-15(31)17(33)20(44-12)27-5-4-13(30)26-23(27)37/h4-5,8-9,11-12,14-18,20,22,28,31-33H,6-7H2,1-3H3,(H,24,34)(H,25,29)(H,35,36)(H,38,39)(H,40,41)(H,26,30,37)/t8-,9+,11+,12+,14+,15+,16+,17+,18+,20+,22?/m0/s1
CAS number:	78738-65-5
IUPAC Name:	(2S)-2-{[(2R)-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}propanoic acid
Traditional IUPAC Name:	(2S)-2-{[(2R)-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}propanoic 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)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Pyrimidine nucleotides
Sub Class	Pyrimidine nucleotide sugars
Direct Parent	Pyrimidine nucleotide sugars
Alternative Parents	Pyrimidine ribonucleoside diphosphates Pentose phosphates N-acyl-alpha-hexosamines N-acyl-L-alpha-amino acids Alanine and derivatives Glycosylamines Monosaccharide phosphates Organic pyrophosphates Pyrimidones Monoalkyl phosphates Hydropyrimidines Oxanes Heteroaromatic compounds Acetamides Vinylogous amides Tetrahydrofurans Secondary alcohols Secondary carboxylic acid amides Lactams Ureas Oxacyclic compounds Azacyclic compounds Carboxylic acids Dialkyl ethers Monocarboxylic acids and derivatives Carbonyl compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Primary alcohols Organopnictogen compounds
Substituents	Pyrimidine nucleotide sugar Pyrimidine ribonucleoside diphosphate Pentose phosphate Pentose-5-phosphate N-acyl-alpha-hexosamine N-acyl-alpha-amino acid N-acyl-l-alpha-amino acid N-acyl-alpha amino acid or derivatives Glycosyl compound N-glycosyl compound Alanine or derivatives Alpha-amino acid or derivatives Monosaccharide phosphate Organic pyrophosphate Monoalkyl phosphate Pyrimidone Alkyl phosphate Pyrimidine Phosphoric acid ester Hydropyrimidine Oxane Monosaccharide Organic phosphoric acid derivative Tetrahydrofuran Vinylogous amide Acetamide Heteroaromatic compound Secondary carboxylic acid amide Secondary alcohol Urea Carboxamide group Lactam Carboxylic acid derivative Carboxylic acid Dialkyl ether Ether Organoheterocyclic compound Monocarboxylic acid or derivatives Azacycle Oxacycle Organopnictogen compound Organic oxygen compound Carbonyl group Primary alcohol Organooxygen compound Organic nitrogen compound Organic oxide Organonitrogen compound Hydrocarbon derivative Alcohol Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	glyco-amino acid (CHEBI:16932 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source LogP: -6.528 PhysProp
Predicted Properties	Property Value Source Water Solubility 17.3 g/L ALOGPS logP -1.3 ALOGPS logP -3.1 ChemAxon logS -1.6 ALOGPS pKa (Strongest Acidic) 1.73 ChemAxon pKa (Strongest Basic) -3.7 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 20 ChemAxon Hydrogen Donor Count 10 ChemAxon Polar Surface Area 366.28 Ų ChemAxon Rotatable Bond Count 15 ChemAxon Refractivity 151.55 m³·mol⁻¹ ChemAxon Polarizability 64.63 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 + D-Glutamic acid + UDP-N-Acetylmuramoyl-L-alanine <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate L-Alanine + Adenosine triphosphate + UDP-N-Acetylmuraminate <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanine Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanine + D-Glutamic acid <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate Adenosine triphosphate + UDP-N-Acetylmuraminate + L-Alanine <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanine D-Glutamic acid + UDP-N-Acetylmuramoyl-L-alanine + Adenosine triphosphate > Hydrogen ion + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate + Phosphate + ADP Adenosine triphosphate + UDP-N-Acetylmuraminate + L-Alanine > ADP + Inorganic phosphate + UDP-N-Acetylmuramoyl-L-alanine Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanine + DL-Glutamic acid > ADP + Inorganic phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate UDP-N-acetylmuraminate + Adenosine triphosphate + L-Alanine + UDP-N-Acetylmuraminate + L-Alanine > UDP-N-Acetylmuramoyl-L-alanine + Adenosine diphosphate + Phosphate + ADP UDP-N-Acetylmuramoyl-L-alanine + Adenosine triphosphate + D-Glutamic acid > Adenosine diphosphate + Phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + ADP + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate UDP-N-acetyl-α-D-muramate + L-Alanine + Adenosine triphosphate + L-Alanine > Adenosine diphosphate + Phosphate + Hydrogen ion + UDP-N-Acetylmuramoyl-L-alanine + ADP L-Alanine + Adenosine triphosphate + UDP-N-Acetylmuraminate <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanine Adenosine triphosphate + D-Glutamic acid + UDP-N-Acetylmuramoyl-L-alanine <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate L-Alanine + Adenosine triphosphate + UDP-N-Acetylmuraminate <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanine Adenosine triphosphate + D-Glutamic acid + UDP-N-Acetylmuramoyl-L-alanine <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate
SMPDB Pathways:	D-Glutamine and D-glutamate metabolism PW000769 peptidoglycan biosynthesis I PW000906
KEGG Pathways:	D-Glutamine and D-glutamate metabolism ec00471 Metabolic pathways eco01100 Peptidoglycan biosynthesis ec00550
EcoCyc Pathways:	UDP-N-acetylmuramoyl-pentapeptide biosynthesis III (meso-DAP-containing) PWY-6387
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-03di-5900000200-10c08e7fa5be20ae1807 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03di-5900000000-c709a71b4651bce45ce7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03du-9400000000-c0d9160051e7f7f2b7a0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-8914303600-11b64513dcd6d6c45ba1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-08gl-9713130300-9485d5c1d45c8be86f5b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-06tf-5912000000-6bffb4709eadd4c8f246 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:	Humljan, J., Kotnik, M., Contreras-Martel, C., Blanot, D., Urleb, U., Dessen, A., Solmajer, T., Gobec, S. (2008). "Novel naphthalene-N-sulfonyl-D-glutamic acid derivatives as inhibitors of MurD, a key peptidoglycan biosynthesis enzyme." J Med Chem 51:7486-7494. Pubmed: 19007109 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 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 16932 HMDB ID Not Available Pubchem Compound ID 23724467 Kegg ID C01212 ChemSpider ID 388547 Wikipedia ID Not Available BioCyc ID CPD0-1456 EcoCyc ID CPD0-1456

Enzymes