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Record Information
Version	2.0
Creation Date	2012-05-31 14:50:41 -0600
Update Date	2015-06-03 17:20:18 -0600
Secondary Accession Numbers	ECMDB20560
Identification
Name:	Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate
Description	Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate or C5PP GlcNAc is involved in ECA biosynthesis. It is a substrate for Undecaprenyl-phosphate alpha-N-acetylglucosaminyl 1-phosphate transferase. This enzyme catalyzes the transfer of the GlcNAc-1-phosphate moiety from UDP-GlcNAc onto the carrier lipid undecaprenyl phosphate (C55-P), yielding GlcNAc-pyrophosphoryl-undecaprenyl (GlcNAc-PP-C55). It is the first lipid-linked intermediate involved in enterobacterial common antigen (ECA) synthesis and an acceptor for the addition of subsequent sugars to complete the biosynthesis of O-antigen (PMID 1730666). GlcNAc-pyrophosphorylundecaprenol functions as the acceptor of mannose residues for the in vivo synthesis of O8 side chains in E. coli.(PMID 7514591). Enterobacterial common antigen (ECA) is an outer membrane glycolipid common to all members of Enterobacteriaceae. The carbohydrate portion consists of N-acetyl-glucosamine, N-acetyl-D-mannosaminuronic acid and 4-acetamido-4,6-dideoxy-D-galactose. These amino sugars form trisaccharide repeat units which are part of linear heteropolysaccharide chains.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xb4043b70> Close
Synonyms:	N-acetyl-D-glucosaminyldiphospho-undecaprenol N-acetyl-D-glucosaminyldiphosphoundecaprenol N-acetyl-glucosaminyl-pyrophosphorylundecaprenol N-[4,5-dihydroxy-2-[hydroxy-(hydroxy-(3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaenoxy)phosphinoyl)oxy-phosphinoyl]oxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide C55-PP-GlcNAc Ditrans,polycis-undecaprenyl-N-acetyl-D-glucosaminyl diphosphate Ditrans,polycis-undecaprenyl-N-acetyl-D-glucosaminyl diphosphoric acid Glcnac-PP-lipid Glcnac-pyrophosphorylundecaprenol Lipid I N-Acetyl-D-glucosaminyldiphospho-undecaprenol N-Acetyl-D-glucosaminyldiphosphoundecaprenol N-Acetyl-glucosaminyl-pyrophosphorylundecaprenol N-[4,5-Dihydroxy-2-[hydroxy-(hydroxy-(3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaenoxy)phosphinoyl)oxy-phosphinoyl]oxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide Prenyl-P-P-GlcNAc Undecaprenyl diphospho N-acetyl-glucosamine Undecaprenyl-N-acetyl-α-D-glucosaminyl-pyrophosphate Undecaprenyl-N-acetyl-D-glucosaminyl-pyrophosphate Undecaprenyl-n-acetyl-α-D-glucosaminyl-pyrophosphate Undecaprenyl-n-acetyl-α-D-glucosaminyl-pyrophosphoric acid Undecaprenyl-N-acetyl-a-D-glucosaminyl-pyrophosphate Undecaprenyl-N-acetyl-a-D-glucosaminyl-pyrophosphoric acid Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphoric acid Undecaprenyl-N-acetyl-D-glucosaminyl-pyrophosphate Undecaprenyl-n-acetyl-D-glucosaminyl-pyrophosphoric acid Undecaprenyl-N-acetyl-D-glucosaminyl-pyrophosphoric acid Undecaprenyl-N-acetyl-α-D-glucosaminyl-pyrophosphate Undecaprenyl-N-acetyl-α-D-glucosaminyl-pyrophosphoric acid
Chemical Formula:	C63H105NO12P2
Weight:	Average: 1130.4548 Monoisotopic: 1129.711200853
InChI Key:	NEVJGTXBHJNFAZ-UHFFFAOYSA-N
InChI:	InChI=1S/C63H105NO12P2/c1-47(2)24-14-25-48(3)26-15-27-49(4)28-16-29-50(5)30-17-31-51(6)32-18-33-52(7)34-19-35-53(8)36-20-37-54(9)38-21-39-55(10)40-22-41-56(11)42-23-43-57(12)44-45-73-77(69,70)76-78(71,72)75-63-60(64-58(13)66)62(68)61(67)59(46-65)74-63/h24,26,28,30,32,34,36,38,40,42,44,59-63,65,67-68H,14-23,25,27,29,31,33,35,37,39,41,43,45-46H2,1-13H3,(H,64,66)(H,69,70)(H,71,72)
CAS number:	Not Available
IUPAC Name:	N-(4,5-dihydroxy-2-{[hydroxy({hydroxy[(3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl)oxy]phosphoryl}oxy)phosphoryl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid
Traditional IUPAC Name:	N-[4,5-dihydroxy-2-({hydroxy[hydroxy(3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl)oxyphosphoryl]oxyphosphoryl}oxy)-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid
SMILES:	CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(O)(=O)OP(O)(=O)OC1OC(CO)C(O)C(O)C1N=C(C)O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Prenol lipids
Sub Class	Polyprenols
Direct Parent	Polyprenyl phospho carbohydrates
Alternative Parents	Polyterpenoids Bactoprenol diphosphates Polyprenyl monophosphates N-acyl-alpha-hexosamines Hexoses Isoprenoid phosphates Monosaccharide phosphates Organic pyrophosphates Monoalkyl phosphates Oxanes Acetamides Secondary carboxylic acid amides Secondary alcohols Oxacyclic compounds Organonitrogen compounds Carbonyl compounds Organic oxides Primary alcohols Hydrocarbon derivatives Organopnictogen compounds
Substituents	Polyterpenoid Polyprenyl phospho carbohydrate Bactoprenol diphosphate Polyprenyl monophosphate Polyprenyl phosphate skeleton N-acyl-alpha-hexosamine Hexose monosaccharide Isoprenoid phosphate Monosaccharide phosphate Organic pyrophosphate Monoalkyl phosphate Monosaccharide Organic phosphoric acid derivative Oxane Phosphoric acid ester Alkyl phosphate Acetamide Carboxamide group Secondary carboxylic acid amide Secondary alcohol Oxacycle Carboxylic acid derivative Organoheterocyclic compound Carbonyl group Organic oxide Alcohol Organopnictogen compound Organic oxygen compound Organic nitrogen compound Hydrocarbon derivative Primary alcohol Organonitrogen compound Organooxygen compound Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.00039 g/L ALOGPS logP 8.48 ALOGPS logP 14.82 ChemAxon logS -6.5 ALOGPS pKa (Strongest Acidic) 1.88 ChemAxon pKa (Strongest Basic) 1.2 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 10 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 204.8 Ų ChemAxon Rotatable Bond Count 39 ChemAxon Refractivity 330.92 m³·mol⁻¹ ChemAxon Polarizability 132.72 ų ChemAxon Number of Rings 1 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:	Membrane
Reactions:	Uridine diphosphate-N-acetylglucosamine + Undecaprenyl phosphate > Uridine 5'-monophosphate + Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate UDP-N-Acetyl-D-mannosaminouronate + Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate > Hydrogen ion + Uridine 5'-diphosphate + Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronate Di-trans,poly-cis-undecaprenyl phosphate + Uridine diphosphate-N-acetylglucosamine <> Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate + Uridine 5'-monophosphate Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate + UDP-N-Acetyl-D-mannosaminouronate <> Hydrogen ion + Undecaprenyl phosphate + Uridine 5'-diphosphate Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate + UDP-ManNAcA > Uridine 5'-diphosphate + Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronate + Hydrogen ion
SMPDB Pathways:	Secondary Metabolites: enterobacterial common antigen biosynthesis 3 PW002046
KEGG Pathways:	Not Available
EcoCyc Pathways:	enterobacterial common antigen biosynthesis ECASYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-01ot-3621000901-6ff614f5acc94b6280c1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0002-0121000910-05f0454830cf4b971ea3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0002-0121110900-1aecb86a3bd5b807a31c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0570-9400000004-0138b8e07cb3c1938f1b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0a6r-7925000203-a87f9fb6aa9386a53c00 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4l-4900000000-e4caa11e9b995ebfdc61 View in MoNA MS Mass Spectrum (Electron Ionization) Not Available View in JSpectraViewer
References
References:	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 Rick, P. D., Hubbard, G. L., Barr, K. (1994). "Role of the rfe gene in the synthesis of the O8 antigen in Escherichia coli K-12." J Bacteriol 176:2877-2884. Pubmed: 7514591 Rick, P. D., Mayer, H., Neumeyer, B. A., Wolski, S., Bitter-Suermann, D. (1985). "Biosynthesis of enterobacterial common antigen." J Bacteriol 162:494-503. Pubmed: 3886625 Zheng, Y., Struck, D. K., Bernhardt, T. G., Young, R. (2008). "Genetic analysis of MraY inhibition by the phiX174 protein E." Genetics 180:1459-1466. Pubmed: 18791230
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID Not Available Pubchem Compound ID 182 Kegg ID Not Available ChemSpider ID 177 Wikipedia ID Not Available BioCyc ID ACETYL-D-GLUCOSAMINYLDIPHOSPHO-UNDECAPRE EcoCyc ID ACETYL-D-GLUCOSAMINYLDIPHOSPHO-UNDECAPRE

Enzymes