P. aeruginosa Metabolome Database: UDP-<i>N</i>-acetyl-α-D-muramoyl-L-alanyl-D-glutamate (PAMDB110517)

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

PAMDB110517

Identification

Name:

UDP-N-acetyl-α-D-muramoyl-L-alanyl-D-glutamate

Description:

Tetraanion of UDP-N-acetylmuramoyl-L-alanyl-D-glutamic acid arising from deprotonation of the diphosphate and glutamate carboxy groups; major species at pH 7.3.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

UDP-N-acetyl-α-D-muramoyl-L-alanyl-D-glutamate 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)

Chemical Formula:

C₂₈H₃₉N₅O₂₃P₂

Average Molecular Weight:

875.58

Monoisotopic Molecular Weight:

879.1824057346

InChI Key:

OJZCATPXPWFLHF-HPUCEMLMSA-J

InChI:

InChI=1S/C28H43N5O23P2/c1-10(23(42)31-13(26(44)45)4-5-17(37)38)29-24(43)11(2)52-22-18(30-12(3)35)27(54-14(8-34)20(22)40)55-58(49,50)56-57(47,48)51-9-15-19(39)21(41)25(53-15)33-7-6-16(36)32-28(33)46/h6-7,10-11,13-15,18-22,25,27,34,39-41H,4-5,8-9H2,1-3H3,(H,29,43)(H,30,35)(H,31,42)(H,37,38)(H,44,45)(H,47,48)(H,49,50)(H,32,36,46)/p-4/t10-,11+,13+,14+,15+,18+,19+,20+,21+,22+,25+,27+/m0/s1

CAS number:

Not Available

IUPAC Name:

Not Available

Traditional IUPAC Name:

Not Available

SMILES:

CC(NC(=O)C(C)OC1(C(C(OC(C(O)1)CO)OP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N3(C=CC(=O)NC(=O)3)))NC(C)=O))C(=O)NC(CCC([O-])=O)C(=O)[O-]

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a UDP-sugar (UDP-AA-GLUTAMATE)

Physical Properties

State:

Not Available

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Not Available

Predicted Properties

Property	Value	Source
Molecular Weight	875.58 g/mol	PubChem
XLogP3-AA	-6	PubChem
Hydrogen Bond Donor Count	8	PubChem
Hydrogen Bond Acceptor Count	23	PubChem
Rotatable Bond Count	18	PubChem
Exact Mass	875.151 g/mol	PubChem
Monoisotopic Mass	875.151 g/mol	PubChem
Topological Polar Surface Area	434 A^2	PubChem
Heavy Atom Count	58	PubChem
Formal Charge	-4	PubChem
Complexity	1670	PubChem
Isotope Atom Count	0	PubChem
Defined Atom Stereocenter Count	12	PubChem
Undefined Atom Stereocenter Count	0	PubChem
Defined Bond Stereocenter Count	0	PubChem
Undefined Bond Stereocenter Count	0	PubChem
Covalently-Bonded Unit Count	1	PubChem

Biological Properties

Cellular Locations:

Not Available

Reactions:

Pathways:

KDO₂-lipid A and peptidoglycan biosynthesisKDO-PEP-LIPASYN-PWY
peptidoglycan biosynthesis I (meso-diaminopimelate containing)PEPTIDOGLYCANSYN-PWY
peptidoglycan and lipid A precursor biosynthesisPEP-LIPA-SYN-PWY
UDP-N-acetylmuramoyl-pentapeptide biosynthesis I (meso-DAP-containing)PWY-6387
peptidoglycan biosynthesis III (mycobacteria)PWY-6385

Spectra

Spectra:

Not Available

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
ChEBI	57968
IAF1260	35714
KEGG	C00692
PubChem	25243858

UDP-N-acetyl-α-D-muramoyl-L-alanyl-D-glutamate (PAMDB110517)

Structure for UDP-N-acetyl-α-D-muramoyl-L-alanyl-D-glutamate (PAMDB110517)