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Record Information
Version	2.0
Creation Date	2012-05-31 14:31:38 -0600
Update Date	2015-06-03 17:19:28 -0600
Secondary Accession Numbers	ECMDB20178
Identification
Name:	N-Acetylmuramoyl-Ala
Description	N-acetylmuramoyl-Ala is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. 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.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa948f860> Close
Synonyms:	N-Acetyl-D-muramoyl-L-alanine
Chemical Formula:	C14H24N2O9
Weight:	Average: 364.3484 Monoisotopic: 364.148180376
InChI Key:	ICMUIFDBEVJCQA-GQQBCVOHSA-N
InChI:	InChI=1S/C14H24N2O9/c1-5(13(21)22)15-12(20)6(2)24-11-9(16-7(3)18)14(23)25-8(4-17)10(11)19/h5-6,8-11,14,17,19,23H,4H2,1-3H3,(H,15,20)(H,16,18)(H,21,22)/t5-,6-,8-,9-,10-,11-,14+/m1/s1
CAS number:	Not Available
IUPAC Name:	(2R)-2-{[(2R)-2-{[(2S,3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene]amino}propanoic acid
Traditional IUPAC Name:	N-acetylmuramoyl-ala
SMILES:	[H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([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 acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Acylaminosugars
Alternative Parents	N-acyl-alpha-hexosamines N-acyl-alpha amino acids Hexoses Alanine and derivatives Oxanes Acetamides Secondary carboxylic acid amides Secondary alcohols Hemiacetals Oxacyclic compounds Carboxylic acids Dialkyl ethers Monocarboxylic acids and derivatives Organopnictogen compounds Carbonyl compounds Organonitrogen compounds Hydrocarbon derivatives Primary alcohols Organic oxides
Substituents	Acylaminosugar N-acyl-alpha-hexosamine N-acyl-alpha-amino acid N-acyl-alpha amino acid or derivatives Hexose monosaccharide Alanine or derivatives Alpha-amino acid or derivatives Monosaccharide Oxane Acetamide Carboxamide group Hemiacetal Secondary carboxylic acid amide Secondary alcohol Carboxylic acid derivative Carboxylic acid Dialkyl ether Ether Oxacycle Monocarboxylic acid or derivatives Organoheterocyclic compound Alcohol Organopnictogen compound Hydrocarbon derivative Carbonyl group Organic oxide Organic nitrogen compound Primary alcohol Organonitrogen compound Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 3.6 g/L ALOGPS logP -1.3 ALOGPS logP -1.4 ChemAxon logS -2 ALOGPS pKa (Strongest Acidic) 3.45 ChemAxon pKa (Strongest Basic) 1.46 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 11 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 181.63 Ų ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 80.7 m³·mol⁻¹ ChemAxon Polarizability 34.93 ų ChemAxon Number of Rings 1 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:	N-Acetylmuramoyl-Ala + Water <> N-Acetyl-D-muramoate + L-Alanine N-Acetylmuramoyl-Ala + Water <> N-Acetyl-D-muramoate + L-Alanine N-Acetylmuramoyl-Ala + Water <> N-Acetyl-D-muramoate + L-Alanine
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 (Non-derivatized) - 70eV, Positive splash10-02hi-7694000000-e0bf5fe9b2d2e048bb40 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive splash10-000i-4311329000-0c1ade6ce259b701107a View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00kr-9017000000-49af146042561dd04d61 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000f-9134000000-7c4b46985351f5e9e6dc View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000f-9010000000-5935588444947cb43c2a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-029j-6259000000-6ddc444f06283771e5c0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0r71-9356000000-c39ea16c30cb37b25925 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0pbi-9400000000-03d5770d0afc2689d6e4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00kb-0059000000-d9ae8951c5f88ada4a96 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0udj-2191000000-d2139808551a4a8e51f7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0006-9220000000-ebbb1f935552487c02cd View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0ita-1369000000-e1eba374c3c7cc93f250 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0il1-5592000000-c09ca504da13e57364b3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9440000000-56c6db47c0e309352b38 View in MoNA 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 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer
References
References:	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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID HMDB0060494 Pubchem Compound ID 5462248 Kegg ID C02999 ChemSpider ID 4575343 Wikipedia ID Not Available BioCyc ID Not Available

Enzymes