ECMDB: UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine (ECMDB04167) (M2MDB000647)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (977)

Record Information

Version

2.0

Creation Date

2012-05-31 14:07:06 -0600

Update Date

2015-06-03 15:54:49 -0600

Secondary Accession Numbers

ECMDB04167

Identification

Name:

UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine

Description

UDP-n-acetyl-3-(1-carboxyvinyl)-D-glucosamine is a member of the chemical class known as Pyrimidine Nucleotide Sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

Enolpyruvyl-UDP-N-acetylglucosamine
EP-UDPGlCNAC
UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine
UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine
UDP-N-acetylglucosamine-3-O-pyruvate ether
UDP-GlcNAc-enolpyruvate
UDP-GlcNAc-enolpyruvic acid
UDP-GlcNAc-pyruvate enol ether
UDP-GlcNAc-pyruvic acid enol ether
UDP-GlcNacPyrEE
UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine
UDP-N-Acetyl-3-O-(1-carboxyvinyl)-D-glucosamine
UDP-N-Acetylenolpyruvylglucosamine
UDP-N-Acetylglucosamine enolpyruvate
UDP-N-Acetylglucosamine enolpyruvic acid
UDP-N-Acetylglucosamine-3-O-pyruvate ether
UDP-N-Acetylglucosamine-3-O-pyruvateether
UDP-N-Acetylglucosamine-3-O-pyruvic acid ether
UdPGNAC-enolpyruvate
UdPGNAC-enolpyruvic acid
UNAGEP

Chemical Formula:

C₂₀H₂₉N₃O₁₉P₂

Weight:

Average: 677.4005
Monoisotopic: 677.087048785

InChI Key:

BEGZZYPUNCJHKP-DBYWSUQTSA-N

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)/t9-,10-,12-,13-,14-,15-,16-,17-,19-/m1/s1

CAS number:

70222-94-5

IUPAC Name:

2-{[(2R,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}prop-2-enoic acid

Traditional IUPAC Name:

2-{[(2R,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}prop-2-enoic acid

SMILES:

[H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(OC(=C)C(O)=O)[C@@]2([H])N=C(C)O)O[C@@]([H])(N2C=CC(O)=NC2=O)[C@]([H])(O)[C@]1([H])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
Pentose phosphate
Pentose-5-phosphate
N-acyl-alpha-hexosamine
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Organic pyrophosphate
Pyrimidone
Sugar acid
Monoalkyl phosphate
Alkyl phosphate
Hydropyrimidine
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Pyrimidine
Vinylogous amide
Tetrahydrofuran
Heteroaromatic compound
Acetamide
Secondary alcohol
Carboxamide group
Secondary carboxylic acid amide
Urea
Lactam
Oxacycle
Azacycle
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Alcohol
Organopnictogen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Primary alcohol
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine (CHEBI:68507 )

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	18.6 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-3.5	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.7	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	134.15 m³·mol⁻¹	ChemAxon
Polarizability	56.58 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:

Not Available

KEGG Pathways:

Amino sugar and nucleotide sugar metabolism ec00520
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 GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_74) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0910003000-11c12eaadbbfd5b5e021	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2911000000-b27da2682655d5af483d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-4910000000-f2fcc76c834ceb1b1bc7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dl-9842417000-d8491df474af1bf680a3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06r6-9803402000-7d2fde68c6bad3fbc412	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06r6-5912000000-344fcfd8dfc9853678df	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

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

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	16435
HMDB ID	Not Available
Pubchem Compound ID	172502
Kegg ID	C04631
ChemSpider ID	10128141
Wikipedia ID	Not Available
BioCyc ID	UDP-ACETYL-CARBOXYVINYL-GLUCOSAMINE
EcoCyc ID	UDP-ACETYL-CARBOXYVINYL-GLUCOSAMINE
Ligand Expo	EPU

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-acetylglucosamine 1-carboxyvinyltransferase

General function:: Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:: Cell wall formation. Adds enolpyruvyl to UDP-N- acetylglucosamine. Target for the antibiotic phosphomycin
Gene Name:: murA
Uniprot ID:: P0A749
Molecular weight:: 44817

Reactions

Phosphoenolpyruvate + UDP-N-acetyl-D-glucosamine = phosphate + UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine.

UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine (ECMDB04167) (M2MDB000647)

Structure for #<Compound:0xab3e2fdc>

Enzymes

Reactions

Reactions