P. aeruginosa Metabolome Database: UDP-<i>N</i>-acetyl-α-D-glucosamine-enolpyruvate (PAMDB110516)

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

PAMDB110516

Identification

Name:

UDP-N-acetyl-α-D-glucosamine-enolpyruvate

Description:

A UDP-N-acetyl-3-O-(1-carboxylatovinyl)-D-glucosamine(3−) in which the anomeric centre of the glucosamine fragment has α-configuration.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

UDP-N-acetyl-3-O-(1-carboxyvinyl)-α-D-glucosamine
UDP-N-acetyl-α-D-glucosamine-3-O-pyruvate ether
UDP-N-acetyl-3-(1-carboxyvinyl)-α-D-glucosamine
UDP-GlcNAc-pyruvate enol ether
UDP-GlcNAc-enolpyruvate

Chemical Formula:

C₂₀H₂₆N₃O₁₉P₂

Average Molecular Weight:

674.38

Monoisotopic Molecular Weight:

677.0870487864

InChI Key:

BEGZZYPUNCJHKP-DBYWSUQTSA-K

InChI:

InChI=1S/C20H29N3O19P2/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/h3-4,9-10,12-17,19,24,27-29H,1,5-6H2,2H3,(H,21,25)(H,30,31)(H,33,34)(H,35,36)(H,22,26,32)/p-3/t9-,10-,12-,13-,14-,15-,16-,17-,19-/m1/s1

CAS number:

Not Available

IUPAC Name:

uridine 5'-{3-[2-acetamido-3-O-(1-carboxylatoethenyl)-2-deoxy-α-D-glucopyranosyl] diphosphate}

Traditional IUPAC Name:

Not Available

SMILES:

C=C(OC3(C(O)C(CO)OC(OP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N2(C=CC(=O)NC(=O)2)))C(NC(C)=O)3))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
Pentose-5-phosphate
Pentose phosphate
N-acyl-alpha-hexosamine
N-glycosyl compound
Glycosyl compound
Organic pyrophosphate
Monosaccharide phosphate
Pyrimidone
Sugar acid
Oxane
Pyrimidine
Phosphoric acid ester
Hydropyrimidine
Alkyl phosphate
Monosaccharide
Organic phosphoric acid derivative
Heteroaromatic compound
Acetamide
Vinylogous amide
Tetrahydrofuran
Lactam
Urea
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Oxacycle
Alcohol
Carbonyl group
Organonitrogen compound
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic anion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a UDP-sugar (UDP-ACETYL-CARBOXYVINYL-GLUCOSAMINE)

Physical Properties

State:

Not Available

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Not Available

Predicted Properties

Property	Value	Source
Molecular Weight	674.378 g/mol	PubChem
XLogP3-AA	-5.1	PubChem
Hydrogen Bond Donor Count	6	PubChem
Hydrogen Bond Acceptor Count	19	PubChem
Rotatable Bond Count	12	PubChem
Exact Mass	674.064 g/mol	PubChem
Monoisotopic Mass	674.064 g/mol	PubChem
Topological Polar Surface Area	335 A^2	PubChem
Heavy Atom Count	44	PubChem
Formal Charge	-3	PubChem
Complexity	1260	PubChem
Isotope Atom Count	0	PubChem
Defined Atom Stereocenter Count	9	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	68483
IAF1260	44212
KEGG	C04631
PubChem	25244881

UDP-N-acetyl-α-D-glucosamine-enolpyruvate (PAMDB110516)

Structure for UDP-N-acetyl-α-D-glucosamine-enolpyruvate (PAMDB110516)