ECMDB: N-Acetyl-D-muramoate (ECMDB20176) (M2MDB001023)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (7)Transporters (6)XML

Proteins (1071)

Record Information

Version

2.0

Creation Date

2012-05-31 14:31:32 -0600

Update Date

2015-06-03 17:19:28 -0600

Secondary Accession Numbers

ECMDB20176

Identification

Name:

N-Acetyl-D-muramoate

Description

N-acetyl-D-muramoate is a member of the chemical class known as Sugar Acids and Derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group. UDP-N-acetylmuramic acid (UDP-MurNAc) is a precursor for peptidoglycan biosynthesis in bacteria. (PMID 14659546) Peptidoglycan is the major constituent of the cell wall, which is comprised of backbone repeats of N-acetylglucosamine (NAG) and N-acetylmuramic acid (NAM). (PMID 18700763) UDP-N-acetylmuramic acid (UDP-MurNAc) is a potent inhibitor of MurA (enolpyruvyl-UDP-GlcNAc synthase). (PMID 15751977) The bacterial cell wall is a polymer consisting of alternating N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc) units, cross-linked via peptides appended to MurNAc. (PMID 12369847). 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

MOL SDF PDB SMILES InChI

Synonyms:

N-Acetyl-D-muramoic acid
N-Acetylmuramate
N-Acetylmuramic acid

Chemical Formula:

C₁₁H₁₉NO₈

Weight:

Average: 293.2705
Monoisotopic: 293.111066589

InChI Key:

MNLRQHMNZILYPY-MKFCKLDKSA-N

InChI:

InChI=1S/C11H19NO8/c1-4(10(16)17)19-9-7(12-5(2)14)11(18)20-6(3-13)8(9)15/h4,6-9,11,13,15,18H,3H2,1-2H3,(H,12,14)(H,16,17)/t4-,6-,7-,8-,9-,11?/m1/s1

CAS number:

61633-75-8

IUPAC Name:

(2R)-2-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid

Traditional IUPAC Name:

(2R)-2-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid

SMILES:

[H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([H])(O)[C@]1([H])N=C(C)O)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

Substituents

Acylaminosugar
Muramic_acid
N-acyl-alpha-hexosamine
Hexose monosaccharide
Sugar acid
Monosaccharide
Oxane
Acetamide
Carboxamide group
Hemiacetal
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Alcohol
Organonitrogen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acetylmuramic acid (CHEBI:21615 )
Amino sugars (C02713 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	53.6 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-1.7	ChemAxon
logS	-0.74	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	1.39	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	149.04 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	62.88 m³·mol⁻¹	ChemAxon
Polarizability	27.39 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	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:

Phosphoenolpyruvic acid + N-Acetyl-D-muramoate > N-Acetylmuramic acid 6-phosphate + Pyruvic acid
N-Acetylmuramoyl-Ala + Water <> N-Acetyl-D-muramoate + L-Alanine
N-Acetyl-D-muramoate + Protein N(pi)-phospho-L-histidine <> N-Acetylmuramic acid 6-phosphate + Protein histidine
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:

Amino sugar and nucleotide sugar metabolism ec00520
Phosphotransferase system (PTS) ec02060

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	splash10-0w3c-9770000000-6ea5f3aa50ac02ceef70	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-000i-2521239000-848f1d85486e26e1ccb1	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-2090000000-c59d76c37f09e9eca3a8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9300000000-c6df138f6c4ab6417c59	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-55e3ebaf861e8b735486	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-5b2b2975a5058255fb08	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-88058a65b8efd6f05e46	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004l-0190000000-66ecbfcb7919cabff2d3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-0910000000-5c3a9f9f979ccddac74d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-1900000000-d14f3f8f84118002dfa5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000j-7900000000-471fe5d4e276658b1949	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000t-9200000000-6adb1379e733b7e32568	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-1810df27f3e35e27f607	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9200000000-e95563bae7228e910e00	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-2900000000-430a64e2453d7fb5e230	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000t-9200000000-de6c564d9edc459bf8a9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-002r-0920000000-22b37e7c518af19310d5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000t-9200000000-c0d7500b262a7d7e8404	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1900000000-71199c968272be0cb202	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-002r-0910000000-a1354bedf1ac9db6c3c6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-052u-9000000000-b9701ee162fa5c198fa7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fbc-0090000000-77705b9680f576293a4f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zor-2190000000-a2225fd0cee643a4a97c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fi3-9570000000-18bd313b1db1b7d803ee	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udv-4190000000-937234965abe7cb8d291	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zmr-7390000000-092457bbe47b41978e3c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-9400000000-f12dba9036850e101fed	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:

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
Mizyed, S., Oddone, A., Byczynski, B., Hughes, D. W., Berti, P. J. (2005). "UDP-N-acetylmuramic acid (UDP-MurNAc) is a potent inhibitor of MurA (enolpyruvyl-UDP-GlcNAc synthase)." Biochemistry 44:4011-4017. Pubmed: 15751977
Raymond, J. B., Price, N. P., Pavelka, M. S. Jr (2003). "A method for the enzymatic synthesis and HPLC purification of the peptidoglycan precursor UDP-N-acetylmuramic acid." FEMS Microbiol Lett 229:83-89. Pubmed: 14659546
Schwartz, B., Markwalder, J. A., Seitz, S. P., Wang, Y., Stein, R. L. (2002). "A kinetic characterization of the glycosyltransferase activity of Eschericia coli PBP1b and development of a continuous fluorescence assay." Biochemistry 41:12552-12561. Pubmed: 12369847
Suvorov, M., Lee, M., Hesek, D., Boggess, B., Mobashery, S. (2008). "Lytic transglycosylase MltB of Escherichia coli and its role in recycling of peptidoglycan strands of bacterial cell wall." J Am Chem Soc 130:11878-11879. Pubmed: 18700763
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

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	21615
HMDB ID	HMDB0060493
Pubchem Compound ID	5462244
Kegg ID	C02713
ChemSpider ID	4575341
Wikipedia ID	N-Acetylmuramic_acid
BioCyc ID	Not Available

Enzymes

Protein Details

1. Phosphoenolpyruvate-protein phosphotransferase

General function:: Involved in transferase activity, transferring phosphorus-containing groups
Specific function:: General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. Enzyme I transfers the phosphoryl group from phosphoenolpyruvate (PEP) to the phosphoryl carrier protein (HPr)
Gene Name:: ptsI
Uniprot ID:: P08839
Molecular weight:: 63561

Reactions

Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine.

Protein Details

2. N-acetylmuramoyl-L-alanine amidase AmiB

General function:: Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:: Cell-wall hydrolase probably involved in cell-wall hydrolysis, septation or recycling
Gene Name:: amiB
Uniprot ID:: P26365
Molecular weight:: 47985

Reactions

Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.

Protein Details

3. Probable N-acetylmuramoyl-L-alanine amidase AmiA

General function:: Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:: Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides
Gene Name:: amiA
Uniprot ID:: P36548
Molecular weight:: 31412

Reactions

Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.

Protein Details

4. N-acetylmuramoyl-L-alanine amidase AmiC

General function:: Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:: Cell-wall hydrolase probably involved in cell-wall hydrolysis, septation or recycling
Gene Name:: amiC
Uniprot ID:: P63883
Molecular weight:: 45634

Reactions

Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.

Protein Details

5. Glucose-specific phosphotransferase enzyme IIA component

General function:: Involved in sugar:hydrogen symporter activity
Specific function:: The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucose transport
Gene Name:: crr
Uniprot ID:: P69783
Molecular weight:: 18251

Reactions

Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.

Protein Details

6. PTS system N-acetylmuramic acid-specific EIIBC component

General function:: Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:: The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in N-acetylmuramic acid (MurNAc) transport, yielding cytoplasmic MurNAc-6-P. Is responsible for growth on MurNAc as the sole source of carbon and energy. Is also able to take up anhydro-N-acetylmuramic acid (anhMurNAc), but cannot phosphorylate the carbon 6, probably because of the 1,6- anhydro ring
Gene Name:: murP
Uniprot ID:: P77272
Molecular weight:: 49801

Reactions

Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.

Protein Details

7. Phosphocarrier protein HPr

General function:: Involved in sugar:hydrogen symporter activity
Specific function:: General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. The phosphoryl group from phosphoenolpyruvate (PEP) is transferred to the phosphoryl carrier protein HPr by enzyme I. Phospho-HPr then transfers it to the permease (enzymes II/III)
Gene Name:: ptsH
Uniprot ID:: P0AA04
Molecular weight:: 9119

Reactions

Protein HPr N(pi)-phospho-L-histidine + protein EIIA = protein HPr + protein EIIA N(tau)-phospho-L-histidine.

Transporters

Protein Details

1. PTS system N-acetylmuramic acid-specific EIIBC component

General function:: Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:: The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in N-acetylmuramic acid (MurNAc) transport, yielding cytoplasmic MurNAc-6-P. Is responsible for growth on MurNAc as the sole source of carbon and energy. Is also able to take up anhydro-N-acetylmuramic acid (anhMurNAc), but cannot phosphorylate the carbon 6, probably because of the 1,6- anhydro ring
Gene Name:: murP
Uniprot ID:: P77272
Molecular weight:: 49801

Reactions

Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.

Protein Details

2. Sugar efflux transporter C

General function:: Involved in transmembrane transport
Specific function:: Involved in the efflux of sugars. The physiological role may be the detoxification of non-metabolizable sugar analogs
Gene Name:: setC
Uniprot ID:: P31436
Molecular weight:: 43493

Protein Details

3. Outer membrane protein N

General function:: Involved in transporter activity
Specific function:: Non-specific porin
Gene Name:: ompN
Uniprot ID:: P77747
Molecular weight:: 41220

Protein Details

4. Outer membrane pore protein E

General function:: Involved in transporter activity
Specific function:: Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:: phoE
Uniprot ID:: P02932
Molecular weight:: 38922

Protein Details

5. Outer membrane protein F

General function:: Involved in transporter activity
Specific function:: OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:: ompF
Uniprot ID:: P02931
Molecular weight:: 39333

Protein Details

6. Outer membrane protein C

General function:: Involved in transporter activity
Specific function:: Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:: ompC
Uniprot ID:: P06996
Molecular weight:: 40368

N-Acetyl-D-muramoate (ECMDB20176) (M2MDB001023)

Structure for #<Compound:0xb2d933f4>

Enzymes

Reactions

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Transporters

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