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Record Information
Version	2.0
Creation Date	2015-09-08 17:50:21 -0600
Update Date	2015-09-14 16:46:43 -0600
Secondary Accession Numbers	ECMDB24238
Identification
Name:	UDP-N-acetyl-α-D-muramate
Description	UDP-N-acetyl-alpha-D-muramate is an intermediate in UDP-N-acetylmuramoyl-pentapeptide biosynthesis I (meso-diaminopimelate containing) pathway in E.coli. It is a substrate for the enzyme UDP-N-acetylmuramate-alanine ligase which catalyzes the reaction L-alanine + UDP-N-acetyl-alpha-D-muramate + ATP → UDP-N-acetyl-alpha-D-muramoyl-L-alanine + ADP + phosphate + H+. It is also a product for enzyme UDP-N-acetylenolpyruvoylglucosamine reductase which catalyzes reaction UDP-N-acetyl-alpha-D-glucosamine-enolpyruvate + NADPH + H+ -> UDP-N-acetyl-alpha-D-muramate + NADP+ (BioCyc compound: UDP-N-ACETYLMURAMATE).
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaab89688> Close
Synonyms:	UDP-N-Acetyl-α-D-muramic acid
Chemical Formula:	C20H28N3O19P2
Weight:	Average: 676.395 Monoisotopic: 676.080870429
InChI Key:	NQBRVZNDBBMBLJ-UHFFFAOYSA-K
InChI:	InChI=1S/C20H31N3O19P2/c1-7(18(30)31)38-16-12(21-8(2)25)19(40-9(5-24)14(16)28)41-44(35,36)42-43(33,34)37-6-10-13(27)15(29)17(39-10)23-4-3-11(26)22-20(23)32/h3-4,7,9-10,12-17,19,24,27-29H,5-6H2,1-2H3,(H,21,25)(H,30,31)(H,33,34)(H,35,36)(H,22,26,32)/p-3
CAS number:	Not Available
IUPAC Name:	2-[(2-{[({[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl)oxy]propanoate
Traditional IUPAC Name:	2-({2-[({[5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxyphosphinato)oxy]-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl}oxy)propanoate
SMILES:	CC(OC1C(O)C(CO)OC(OP([O-])(=O)OP([O-])(=O)OCC2OC(C(O)C2O)N2C=CC(=O)NC2=O)C1NC(C)=O)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 Glycosylamines Monosaccharide phosphates Organic pyrophosphates Sugar acids and derivatives Pyrimidones Hydropyrimidines Oxanes Alkyl phosphates Vinylogous amides Heteroaromatic compounds Tetrahydrofurans Acetamides Ureas Secondary carboxylic acid amides Secondary alcohols Lactams Monocarboxylic acids and derivatives Oxacyclic compounds Azacyclic compounds Dialkyl ethers Carboxylic acids Primary alcohols Hydrocarbon derivatives Organic oxides Carbonyl compounds Organonitrogen compounds Organopnictogen compounds Organic anions
Substituents	Pyrimidine nucleotide sugar Pyrimidine ribonucleoside diphosphate Muramic_acid Pentose phosphate Pentose-5-phosphate N-acyl-alpha-hexosamine N-glycosyl compound Glycosyl compound Monosaccharide phosphate Organic pyrophosphate Pyrimidone Sugar acid Alkyl phosphate Phosphoric acid ester Oxane Hydropyrimidine Organic phosphoric acid derivative Pyrimidine Monosaccharide Heteroaromatic compound Acetamide Vinylogous amide Tetrahydrofuran Carboxamide group Lactam Urea Secondary carboxylic acid amide Secondary alcohol Carboxylic acid derivative Organoheterocyclic compound Azacycle Oxacycle Monocarboxylic acid or derivatives Ether Dialkyl ether Carboxylic acid Alcohol Carbonyl group Organonitrogen compound Organooxygen compound Primary alcohol Hydrocarbon derivative Organic oxide Organopnictogen compound Organic oxygen compound Organic nitrogen compound Organic anion Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	a UDP-sugar (UDP-N-ACETYLMURAMATE )
Physical Properties
State:	Not Available
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 26.7 g/L ALOGPS logP -1.2 ALOGPS logP -4.6 ChemAxon logS -1.4 ALOGPS pKa (Strongest Acidic) 1.73 ChemAxon pKa (Strongest Basic) -3.6 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 16 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 335.2 Ų ChemAxon Rotatable Bond Count 13 ChemAxon Refractivity 141.48 m³·mol⁻¹ ChemAxon Polarizability 56.3 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:	UDP-N-acetyl-α-D-glucosamine-enolpyruvate + NADPH + Hydrogen ion + NADPH > NADP + UDP-N-acetyl-α-D-muramate UDP-N-acetyl-α-D-muramate + L-Alanine + Adenosine triphosphate + L-Alanine > Adenosine diphosphate + Phosphate + Hydrogen ion + UDP-N-Acetylmuramoyl-L-alanine + ADP UDP-N-acetyl-α-D-muramate + Adenosine triphosphate + L-Alanine > UDP-N-Acetylmuramyl-L-Ala + ADP + Phosphate + Hydrogen ion
SMPDB Pathways:	Amino sugar and nucleotide sugar metabolism I PW000886 peptidoglycan biosynthesis I PW000906 peptidoglycan biosynthesis I 2 PW002062
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 splash10-004i-0000009000-71055a92a36ec27390b2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0a6r-1001009000-833b340020c68c7d6556 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-074l-9440003000-511197c5404c0dd64958 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-8000009000-a9e600e8a5f8ee1256cb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0006-9200002000-920abe2754e298f139ef View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-000f-9200000000-6f36050197589ac6e610 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:	Not Available
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 Not Available Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available

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