P. aeruginosa Metabolome Database: UDP-<i>N</i>-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine (PAMDB110520)

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

PAMDB110520

Identification

Name:

UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine

Description:

UDP-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alaninate(3−) in which the anomeric centre of the pyranose fragment has α-configuration.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

UDP-Mur2Ac(oyl-L-Ala-g-D-Glu-L-Lys-D-Ala-D-Ala)
UDP-MurNAc-pentapeptide

Chemical Formula:

C₄₀H₆₂N₉O₂₆P₂

Average Molecular Weight:

1146.9

Monoisotopic Molecular Weight:

1150.35942136

InChI Key:

PFMVORMCVGOQKR-XNCOKRRHSA-K

InChI:

InChI=1S/C40H65N9O26P2/c1-16(32(57)44-18(3)37(61)62)43-35(60)21(8-6-7-12-41)46-25(52)10-9-22(38(63)64)47-33(58)17(2)42-34(59)19(4)71-31-27(45-20(5)51)39(73-23(14-50)29(31)55)74-77(68,69)75-76(66,67)70-15-24-28(54)30(56)36(72-24)49-13-11-26(53)48-40(49)65/h11,13,16-19,21-24,27-31,36,39,50,54-56H,6-10,12,14-15,41H2,1-5H3,(H,42,59)(H,43,60)(H,44,57)(H,45,51)(H,46,52)(H,47,58)(H,61,62)(H,63,64)(H,66,67)(H,68,69)(H,48,53,65)/p-3/t16-,17+,18-,19-,21+,22-,23-,24-,27-,28-,29-,30-,31-,36-,39-/m1/s1

CAS number:

Not Available

IUPAC Name:

Not Available

Traditional IUPAC Name:

Not Available

SMILES:

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

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Not Available

Predicted Properties

Property	Value	Source
Molecular Weight	1146.921 g/mol	PubChem
XLogP3-AA	-9.3	PubChem
Hydrogen Bond Donor Count	12	PubChem
Hydrogen Bond Acceptor Count	26	PubChem
Rotatable Bond Count	28	PubChem
Exact Mass	1146.328 g/mol	PubChem
Monoisotopic Mass	1146.328 g/mol	PubChem
Topological Polar Surface Area	549 A^2	PubChem
Heavy Atom Count	77	PubChem
Formal Charge	-3	PubChem
Complexity	2270	PubChem
Isotope Atom Count	0	PubChem
Defined Atom Stereocenter Count	15	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:

UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine + Water → UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanine + D-Alanine
UDP-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysine + D-Alanyl-D-alanine + ATP → Hydrogen ion + UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine + phosphate + ADP
UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine + di-trans,octa-cis-undecaprenyl phosphate → undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysyl- D-alanyl-D-alanine + UMP

Pathways:

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	70758
KEGG	C04846
PubChem	46173209

UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine (PAMDB110520)

Structure for UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine (PAMDB110520)