P. aeruginosa Metabolome Database: 1,6-Anhydro-N-acetylmuramate (PAMDB001327)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB001327

Identification

Name:

1,6-Anhydro-N-acetylmuramate

Description:

1,6-anhMurNAC is an Amino Sugar. These are compounds having one alcoholic hydroxy group replaced by an amino group; systematically known as x-amino-x-deoxymonosaccharides. 1,6-anhydro-N-acetylmuramic acid (anhMurNAc) is one of the components of murein that is recycled inside the cell. Although exogenously provided anhMurNAc can be taken up by Pseudomonas aeruginosa, it can not serve as the sole source of carbon for growth.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

1,6-anhMurNAc
1,6-Anhydro-N-acetylmuramate
1,6-Anhydro-N-acetylmuramic acid

Chemical Formula:

C₁₁H₁₇NO₇

Average Molecular Weight:

275.2552

Monoisotopic Molecular Weight:

275.100501903

InChI Key:

ZFEGYUMHFZOYIY-NFSFVEDMSA-N

InChI:

InChI=1S/C11H17NO7/c1-4(10(15)16)18-9-7(12-5(2)13)11-17-3-6(19-11)8(9)14/h4,6-9,11,14H,3H2,1-2H3,(H,12,13)(H,15,16)/t4?,6-,7-,8-,9-,11?/m1/s1

CAS number:

Not Available

IUPAC Name:

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

Traditional IUPAC Name:

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

SMILES:

[H]C(C)(O[C@@]1([H])[C@]([H])(O)[C@@]2([H])COC([H])(O2)[C@]1([H])N=C(C)O)C(O)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as oxepanes. These are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Oxane
Monosaccharide
Meta-dioxolane
Secondary alcohol
Oxacycle
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
Hydrocarbon derivative
Organooxygen compound
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	45.4 mg/mL	ALOGPS
logP	-0.62	ALOGPS
logP	-0.55	ChemAxon
logS	-0.78	ALOGPS
pKa (Strongest Acidic)	3.54	ChemAxon
pKa (Strongest Basic)	1.36	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.81 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	59.37 m³·mol^-1	ChemAxon
Polarizability	25.7 Å³	ChemAxon
Number of Rings	2	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:

1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide + Water > L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + 1,6-Anhydro-N-acetylmuramate
1,6-Anhydrous-N-Acetylmuramyl-tripeptide + Water > L-alanine-D-glutamate-meso-2,6-diaminoheptanedioate + 1,6-Anhydro-N-acetylmuramate
N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramic acid + Water > N-Acetyl-D-glucosamine + 1,6-Anhydro-N-acetylmuramate
1,6-Anhydro-N-acetylmuramate + Adenosine triphosphate + Water > Hydrogen ion + N-Acetylmuramic acid 6-phosphate + ADP
<i>N</i>-acetyl-β-D-glucosamine(anhydrous)-<i>N</i>-acetylmuramate + Water N-Acetyl-D-glucosamine + 1,6-Anhydro-N-acetylmuramate
Adenosine triphosphate + Water + 1,6-Anhydro-N-acetylmuramate <> Adenosine diphosphate + MurNAc-6-P + ADP

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a7i-0090000000-d65769bdb2b625a1338f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f80-2590000000-363094b06f3083b70e4e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03ki-6910000000-552f488fd871ad624ebb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1090000000-3fb08bcd0c788dcadb4b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pc0-3490000000-7f2d261fd1517d8a2490	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-9700000000-0a49ea8c6cf44dc9233b	View in MoNA

References

References:

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

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	40666
HMDB ID	Not Available
Pubchem Compound ID	25201515
Kegg ID	Not Available
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	CPD0-882
EcoCyc ID	CPD0-882

1,6-Anhydro-N-acetylmuramate (PAMDB001327)

Structure for 1,6-Anhydro-N-acetylmuramate (PAMDB001327)