P. aeruginosa Metabolome Database: GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelyl-D-alanine (PAMDB003536)

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

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB003536

Identification

Name:

GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelyl-D-alanine

Description:

GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelyl-D-alanine is an intermediate in peptidoglycan recylcing and biosynthesis. It is a substrate for the enzyme Murein tetrapeptide carboxypeptidase (lcdA) which releases the terminal D-alanine residue from the cytoplasmic tetrapeptide recycling product L-Ala-gamma-D-Glu-meso-Dap-D-Ala. The tripeptides produced by the lcdA reaction can then be reused as peptidoglycan building blocks.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

GlcNAc-murnac-L-alanyl-g-D-glutamyl-meso-diaminopimelyl-D-alanine
GlcNAc-murnac-L-alanyl-γ-D-glutamyl-meso-diaminopimelyl-D-alanine

Chemical Formula:

C₃₄H₅₇N₇O₁₉

Average Molecular Weight:

867.8519

Monoisotopic Molecular Weight:

867.370922677

InChI Key:

MKQQKXDNMLOSJC-YFCMHDTQSA-N

InChI:

InChI=1S/C34H57N7O19/c1-12(28(51)40-18(8-9-21(46)47)30(53)41-17(7-5-6-16(35)33(56)57)29(52)36-13(2)32(54)55)37-31-22(38-14(3)44)26(50)27(20(11-43)58-31)60-34-23(39-15(4)45)25(49)24(48)19(10-42)59-34/h12-13,16-20,22-27,31,34,37,42-43,48-50H,5-11,35H2,1-4H3,(H,36,52)(H,38,44)(H,39,45)(H,40,51)(H,41,53)(H,46,47)(H,54,55)(H,56,57)/t12-,13+,16-,17+,18+,19+,20+,22+,23+,24+,25+,26+,27+,31+,34-/m0/s1

CAS number:

Not Available

IUPAC Name:

(2S,6R)-2-amino-6-{[(2R)-4-carboxy-2-{[(2S)-2-{[(2R,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]amino}-1-hydroxypropylidene]amino}-1-hydroxybutylidene]amino}-6-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}hexanoic acid

Traditional IUPAC Name:

SMILES:

[H][C@](N)(CCC[C@@]([H])(N=C(O)[C@@]([H])(CCC(O)=O)N=C(O)[C@]([H])(C)N[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])N=C(C)O)[C@]([H])(O)[C@@]1([H])N=C(C)O)C(O)=N[C@]([H])(C)C(O)=O)C(O)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
Saccharolipid
N-acyl-alpha-hexosamine
N-acyl-aliphatic-alpha amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Glucosamine
Amino sugar
O-glycosyl compound
N-glycosyl compound
Glycosyl compound
Disaccharide
D-alpha-amino acid
Alpha-amino acid or derivatives
N-substituted-alpha-amino acid
Alpha-amino acid
Tricarboxylic acid or derivatives
Amino saccharide
Amino fatty acid
Fatty acyl
Oxane
Saccharide
Secondary alcohol
Hemiaminal
1,2-diol
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Secondary aliphatic amine
Carboxylic acid
Carboximidic acid derivative
Carboximidic acid
Acetal
Hydrocarbon derivative
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	0.151 mg/mL	ALOGPS
logP	-2	ALOGPS
logP	-3.2	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	26	ChemAxon
Hydrogen Donor Count	15	ChemAxon
Polar Surface Area	441.74 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	195.98 m³·mol^-1	ChemAxon
Polarizability	84.28 Å³	ChemAxon
Number of Rings	2	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:

GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelyl-D-alanine + Water > GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelate + D-Alanine

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0010100190-9e8437f30e77ca82288d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udl-8173913260-67cfd8fb9e4f7b1e366f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udl-9680720150-1f0385d690fa183cec14	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05p2-3100113890-92d62d11895cdca78711	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0005-1020390020-2d013bb94070609a61d2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0r09-9224233000-16c8934fc82e31b99d3d	View in MoNA

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

GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelyl-D-alanine (PAMDB003536)

Structure for GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelyl-D-alanine (PAMDB003536)