P. aeruginosa Metabolome Database: UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate (PAMDB000649)

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

PAMDB000649

Identification

Name:

UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate

Description:

UDP-n-acetylmuramoyl-L-alanyl-D-glutamate is a member of the chemical class 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. UDP-N-acetylmuramoyl-L-alanyl-D-glutamate 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. UDP-N-acetylmuramoyl-L-alanyl-D-glutamate:meso-diaminopimelate ligase is a cytoplasmic enzyme that catalyzes the addition of meso-diaminopimelic acid to nucleotide precursor UDP-N-acetylmuramoyl-L-alanyl-D-glutamate in the biosynthesis of bacterial cell-wall peptidoglycan. (PMID 11124264)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

UDP-GlcNAcMurAlaGlu
UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate tetraanion
UDP-N-Acetylmuramoyl-L-alanyl-D-glutamic acid
UDP-N-Acetylmuramoyl-L-alanyl-D-glutamic acid tetraanion
Uridine 5'-(3-{2-acetamido-2-deoxy-3-O-[(2R)-1-{[(2S)-1-D-glutamato-1-oxopropan-2-yl]amino}-1-oxopropan-2-yl]-D-glucopyranosyl} diphosphate)
Uridine 5'-(3-{2-acetamido-2-deoxy-3-O-[(2R)-1-{[(2S)-1-D-glutamato-1-oxopropan-2-yl]amino}-1-oxopropan-2-yl]-D-glucopyranosyl} diphosphoric acid)

Chemical Formula:

C₂₂H₃₂Cl₂N₂O₄

Average Molecular Weight:

459.41

Monoisotopic Molecular Weight:

458.1739129

InChI Key:

IEKOTSCYBBDIJC-UHFFFAOYSA-N

InChI:

InChI=1S/C22H32Cl2N2O4/c1-3-5-7-13-26(14-8-6-4-2)22(30)19(11-12-20(27)28)25-21(29)16-9-10-17(23)18(24)15-16/h9-10,15,19H,3-8,11-14H2,1-2H3,(H,25,29)(H,27,28)

CAS number:

17088-64-1

IUPAC Name:

(2R)-2-({2-[(2-{[(3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene}amino)pentanedioic acid

Traditional IUPAC Name:

(2R)-2-({2-[(2-{[(3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene}amino)pentanedioic acid

SMILES:

CCCCCN(CCCCC)C(=O)C(CCC(O)=O)N=C(O)C1=CC(Cl)=C(Cl)C=C1

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine nucleotide sugars

Direct Parent

Pyrimidine nucleotide sugars

Alternative Parents

Substituents

Pyrimidine nucleotide sugar
Pyrimidine ribonucleoside diphosphate
Alpha peptide
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
N-glycosyl compound
Glycosyl compound
Organic pyrophosphate
Monosaccharide phosphate
Alpha-amino acid or derivatives
Hydroxypyrimidine
Monoalkyl phosphate
Amino saccharide
Pyrimidone
Alkyl phosphate
Pyrimidine
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
Organic phosphate
Monosaccharide
Hydropyrimidine
Dicarboxylic acid or derivatives
Saccharide
Heteroaromatic compound
Oxolane
Secondary alcohol
1,2-diol
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source
LogP:	-7.337	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	7.58 mg/mL	ALOGPS
logP	-0.94	ALOGPS
logP	-3.2	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.72	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	24	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	436.17 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	180.16 m³·mol^-1	ChemAxon
Polarizability	76.89 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:

Pathways:

D-Glutamine and D-glutamate metabolism pae00471
Lysine biosynthesis pae00300
Metabolic pathways pae01100
Peptidoglycan biosynthesis pae00550

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0920000030-9501bc6942335865a32b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1910000000-081da383d328cda7011b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-3910000000-47d3cd7d61b410b044d3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-7902600380-4e6fc4dba489cd21009d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03ec-6914104040-1d9c3c55962ac034be03	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06tf-4923000000-36be71bdb3f634865e8d	View in MoNA

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
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
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
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	16970
HMDB ID	Not Available
Pubchem Compound ID	23724464
Kegg ID	C00692
ChemSpider ID	388428
Wikipedia ID	Not Available
BioCyc ID	UDP-AA-GLUTAMATE
EcoCyc ID	UDP-AA-GLUTAMATE

UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate (PAMDB000649)

Structure for UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate (PAMDB000649)