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Record Information

Version

2.0

Creation Date

2012-07-30 14:55:06 -0600

Update Date

2015-06-03 17:21:00 -0600

Secondary Accession Numbers

ECMDB21248

Identification

Name:

N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramic acid

Description

N-acetyl-d-glucosamine(anhydrous)n-acetylmuramic acid belongs to the class of Hexoses. These are monosaccharides in which the sugar unit is a hexose. (inferred from compound structure)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramate

Chemical Formula:

C₁₉H₃₀N₂O₁₂

Weight:

Average: 478.4477
Monoisotopic: 478.179874434

InChI Key:

MWWQKONGFKUAEK-AJSMYUJSSA-N

InChI:

InChI=1S/C19H30N2O12/c1-6(17(27)28)30-16-12(21-8(3)24)18-29-5-10(32-18)15(16)33-19-11(20-7(2)23)14(26)13(25)9(4-22)31-19/h6,9-16,18-19,22,25-26H,4-5H2,1-3H3,(H,20,23)(H,21,24)(H,27,28)/t6?,9-,10?,11-,12?,13-,14-,15?,16?,18?,19+/m1/s1

CAS number:

Not Available

IUPAC Name:

2-[(2-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(1-hydroxyethylidene)amino]-6,8-dioxabicyclo[3.2.1]octan-3-yl)oxy]propanoic acid

Traditional IUPAC Name:

2-[(2-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(1-hydroxyethylidene)amino]-6,8-dioxabicyclo[3.2.1]octan-3-yl)oxy]propanoic acid

SMILES:

CC(OC1C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2N=C(C)O)C2COC(O2)C1N=C(C)O)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acyl-alpha-hexosamines

Alternative Parents

Substituents

N-acyl-alpha-hexosamine
O-glycosyl compound
Glycosyl compound
Disaccharide
Oxepane
Oxane
Meta-dioxolane
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Acetal
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	13.4 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-2	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.34	ChemAxon
pKa (Strongest Basic)	1.64	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	209.32 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	103.4 m³·mol⁻¹	ChemAxon
Polarizability	45.47 Å³	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:

N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide + Water > L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramic acid
N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide + Water > L-alanine-D-glutamate-meso-2,6-diaminoheptanedioate + N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramic acid
N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramic acid + Water > N-Acetyl-D-glucosamine + 1,6-Anhydro-N-acetylmuramate

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 (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-08i9-0010900000-bbda29640fb7ebab3ed5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ug0-1192400000-6c73ff68782ebdf56004	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f79-8988100000-835c46c0f926ef131820	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05br-7255900000-f681ebb93205104715f5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ab9-5294700000-fd1526243bddae3345fa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-059i-9471000000-f13f57a4b77de3859153	View in MoNA
MS	Mass Spectrum (Electron Ionization)	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
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	45479497
Kegg ID	Not Available
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. 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

2. 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

3. 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

4. Beta-hexosaminidase

General function:: Involved in beta-N-acetylhexosaminidase activity
Specific function:: Cleaves GlcNAc linked beta-1,4 to MurNAc tripeptides
Gene Name:: nagZ
Uniprot ID:: P75949
Molecular weight:: 37594

Reactions

Hydrolysis of terminal non-reducing N-acetyl-D-hexosamine residues in N-acetyl-beta-D-hexosaminides.

Protein Details

5. 1,6-anhydro-N-acetylmuramyl-L-alanine amidase AmpD

General function:: Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:: Involved in both cell wall peptidoglycans recycling and beta-lactamase induction. Specifically cleaves the amide bond between the lactyl group of N-acetylmuramic acid and the alpha- amino group of the L-alanine in degradation products containing an anhydro N-acetylmuramyl moiety
Gene Name:: ampD
Uniprot ID:: P13016
Molecular weight:: 20536

Reactions

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

Transporters

Protein Details

1. Protein AmpG

General function:: Involved in transmembrane transport
Specific function:: Probably acts as a permease in the beta-lactamase induction system and in peptidoglycan recycling
Gene Name:: ampG
Uniprot ID:: P0AE16
Molecular weight:: 53245

Protein Details

2. 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

3. 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

4. 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

5. 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

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N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramic acid (M2MDB001656)

Structure for #<Compound:0xac4768a8>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Transporters