ECMDB: UDP-N-Acetylmuraminate (ECMDB03266) (M2MDB000485)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (855)

Record Information

Version

2.0

Creation Date

2012-05-31 13:58:14 -0600

Update Date

2015-09-17 15:41:46 -0600

Secondary Accession Numbers

ECMDB03266

Identification

Name:

UDP-N-Acetylmuraminate

Description

UDP-N-acetylmuaminate is nucleoside diphosphate sugar which is formed from UDP-N-acetylglucosamine and phosphoenolpyruvate. It 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

N-Acetylmuramoyl-UDP
UDP-N-acetyl-D-muramate
UDP-N-acetylmuramic acid
UDP-N-acetylmuramoyl
UDP-MurNaAcA
UDP-MurNAc
UDP-N-Acetyl-D-muramate
UDP-N-Acetyl-D-muramic acid
UDP-N-Acetylmuramate
UDP-N-Acetylmuramic acid
UDP-N-Acetylmuraminic acid
UDP-N-Acetylmuramoyl
Uridine diphosphate N-acetylmuramic acid
Uridine diphosphate N-acetylmuramate
Uridine diphosphate N-acetylmuramic acid
Uridine diphosphoric acid n-acetylmuramic acid
Uridine diphosphoric acid N-acetylmuramic acid

Chemical Formula:

C₂₀H₃₁N₃O₁₉P₂

Weight:

Average: 679.4164
Monoisotopic: 679.102698849

InChI Key:

NQBRVZNDBBMBLJ-UHFFFAOYSA-N

InChI:

InChI=1S/C20H31N3O19P2/c1-7(18(30)31)38-16-12(21-8(2)25)19(40-9(5-24)14(16)28)41-44(35,36)42-43(33,34)37-6-10-13(27)15(29)17(39-10)23-4-3-11(26)22-20(23)32/h3-4,7,9-10,12-17,19,24,27-29H,5-6H2,1-2H3,(H,21,25)(H,30,31)(H,33,34)(H,35,36)(H,22,26,32)

CAS number:

Not Available

IUPAC Name:

(2R)-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}propanoic acid

Traditional IUPAC Name:

(2R)-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}propanoic acid

SMILES:

CC(OC1C(O)C(CO)OC(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=CC(=O)NC2=O)C1NC(C)=O)C(O)=O

Chemical Taxonomy

Description

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
Muramic_acid
Pentose phosphate
Pentose-5-phosphate
N-acyl-alpha-hexosamine
Glycosyl compound
N-glycosyl compound
Organic pyrophosphate
Monosaccharide phosphate
Pyrimidone
Monoalkyl phosphate
Sugar acid
Oxane
Hydropyrimidine
Phosphoric acid ester
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Alkyl phosphate
Acetamide
Vinylogous amide
Heteroaromatic compound
Tetrahydrofuran
Lactam
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Urea
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic nitrogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

UDP-amino sugar (CHEBI:17882 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	15.3 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-3.4	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	333.69 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	133.73 m³·mol⁻¹	ChemAxon
Polarizability	57.36 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:

SMPDB Pathways:

D-Glutamine and D-glutamate metabolism

PW000769

KEGG Pathways:

Amino sugar and nucleotide sugar metabolism ec00520
D-Glutamine and D-glutamate metabolism ec00471
Metabolic pathways eco01100
Peptidoglycan biosynthesis ec00550

EcoCyc Pathways:

UDP-N-acetylmuramoyl-pentapeptide biosynthesis III (meso-DAP-containing) PWY-6387

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0910003000-d2e956d08ef823bacaa5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2911000000-3023ccfbbdfa5463f325	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-4910001000-2bb0105a1963a11e3d5d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-9842417000-056c5806de289dec4ba6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03ec-9712402000-12ec38ff2228757d6a41	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06r6-5912000000-02b514a87ca2c1c9ca6a	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	17882
HMDB ID	HMDB11720
Pubchem Compound ID	1169
Kegg ID	C01050
ChemSpider ID	1136
Wikipedia ID	Not Available
BioCyc ID	UDP-N-ACETYLMURAMATE
EcoCyc ID	UDP-N-ACETYLMURAMATE

Enzymes

Protein Details

1. UDP-N-acetylenolpyruvoylglucosamine reductase

General function:: Involved in flavin adenine dinucleotide binding
Specific function:: Cell wall formation
Gene Name:: murB
Uniprot ID:: P08373
Molecular weight:: 37851

Reactions

UDP-N-acetylmuramate + NADP(+) = UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH.

Protein Details

2. UDP-N-acetylmuramate--L-alanine ligase

General function:: Involved in ATP binding
Specific function:: Cell wall formation
Gene Name:: murC
Uniprot ID:: P17952
Molecular weight:: 53626

Reactions

ATP + UDP-N-acetylmuramate + L-alanine = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanine.

Protein Details

3. UDP-N-acetylmuramate:L-alanyl-gamma-D-glutamyl-meso-diaminopimelate ligase

General function:: Involved in ATP binding
Specific function:: Reutilizes the intact tripeptide L-alanyl-gamma-D- glutamyl-meso-diaminopimelate by linking it to UDP-N-acetylmuramic acid
Gene Name:: mpl
Uniprot ID:: P37773
Molecular weight:: 49874

UDP-N-Acetylmuraminate (ECMDB03266) (M2MDB000485)

Structure for #<Compound:0xa21602e0>

Enzymes

Reactions

Reactions