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Record Information
Version	2.0
Creation Date	2012-07-30 14:55:16 -0600
Update Date	2015-09-17 15:41:48 -0600
Secondary Accession Numbers	ECMDB21298
Identification
Name:	Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronate
Description	Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronateis an intermediate in enterobacterial common antigen (ECA) synthesis. It is a substrate for 4-alpha-L-fucosyltransferase (wecF) This enzyme catalyzes the synthesis of Und-PP-GlcNAc-ManNAcA-Fuc4NAc (Lipid III), the third lipid-linked intermediate involved in ECA synthesis. Enterobacterial common antigen (ECA) is an outer membrane glycolipid similar to LPS that is 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:0xac9a6e2c> Close
Synonyms:	C55-PP-GlcNAc-ManNAcA Lipid II ManNAcA-GlcNAc-PP-lipid ManNAcA-GlcNAc-pyrophosphorylundecaprenol Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronic acid pyrophosphate Undecaprenyl n-acetyl-glucosaminyl-n-acetyl-mannosaminuronic acid pyrophosphoric acid Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronic acid pyrophosphoric acid Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronate Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronic acid
Chemical Formula:	C71H116N2O18P2
Weight:	Average: 1347.6309 Monoisotopic: 1346.769837942
InChI Key:	IGGGNUSEBUZFTR-CDDUTUKUSA-N
InChI:	InChI=1S/C71H116N2O18P2/c1-48(2)25-15-26-49(3)27-16-28-50(4)29-17-30-51(5)31-18-32-52(6)33-19-34-53(7)35-20-36-54(8)37-21-38-55(9)39-22-40-56(10)41-23-42-57(11)43-24-44-58(12)45-46-86-92(82,83)91-93(84,85)90-71-63(73-60(14)76)65(78)67(61(47-74)87-71)88-70-62(72-59(13)75)64(77)66(79)68(89-70)69(80)81/h25,27,29,31,33,35,37,39,41,43,45,61-68,70-71,74,77-79H,15-24,26,28,30,32,34,36,38,40,42,44,46-47H2,1-14H3,(H,72,75)(H,73,76)(H,80,81)(H,82,83)(H,84,85)/b49-27+,50-29+,51-31+,52-33+,53-35+,54-37+,55-39+,56-41+,57-43+,58-45+/t61-,62+,63-,64-,65-,66+,67-,68+,70-,71-/m1/s1
CAS number:	Not Available
IUPAC Name:	(2S,3S,4R,5S,6R)-3,4-dihydroxy-6-{[(2R,3S,4R,5R,6R)-4-hydroxy-6-{[hydroxy({[hydroxy({[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-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}-2-(hydroxymethyl)-5-[(1-oxidoethylidene)amino]oxan-3-yl]oxy}-5-[(1-oxidoethylidene)amino]oxane-2-carboxylate
Traditional IUPAC Name:	(2S,3S,4R,5S,6R)-3,4-dihydroxy-6-{[(2R,3S,4R,5R,6R)-4-hydroxy-6-{[hydroxy({hydroxy[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-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}oxy)phosphoryl]oxy}-2-(hydroxymethyl)-5-[(1-oxidoethylidene)amino]oxan-3-yl]oxy}-5-[(1-oxidoethylidene)amino]oxane-2-carboxylate
SMILES:	OC[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@H](NC(C)=O)[C@@H](O)[C@@H]1O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@@H]1NC(=O)C
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 Disaccharide phosphates O-glycosyl compounds Organic pyrophosphates Isoprenoid phosphates Monoalkyl phosphates Beta hydroxy acids and derivatives Pyrans Oxanes Secondary alcohols Oxacyclic compounds Monocarboxylic acids and derivatives Carboxylic acids Carboximidic acids Acetals Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds Organic anions
Substituents	Polyterpenoid Bactoprenol diphosphate Polyprenyl phospho carbohydrate Polyprenyl monophosphate Polyprenyl phosphate skeleton N-acyl-alpha-hexosamine Disaccharide phosphate O-glycosyl compound Glycosyl compound Disaccharide Organic pyrophosphate Isoprenoid phosphate Monoalkyl phosphate Beta-hydroxy acid Alkyl phosphate Pyran Phosphoric acid ester Oxane Organic phosphoric acid derivative Hydroxy acid Secondary alcohol Oxacycle Organoheterocyclic compound Monocarboxylic acid or derivatives Carboxylic acid Carboxylic acid derivative Carboximidic acid derivative Carboximidic acid Acetal Organic nitrogen compound Organic oxygen compound Organopnictogen compound Organic oxide Hydrocarbon derivative Primary alcohol Organooxygen compound Organonitrogen compound Carbonyl group Alcohol Organic anion 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 0.001 g/L ALOGPS logP 7.46 ALOGPS logP 14.47 ChemAxon logS -6.1 ALOGPS pKa (Strongest Acidic) 1.72 ChemAxon pKa (Strongest Basic) -3.6 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 17 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 321.87 Ų ChemAxon Rotatable Bond Count 43 ChemAxon Refractivity 406.76 m³·mol⁻¹ ChemAxon Polarizability 151.23 ų ChemAxon Number of Rings 2 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:	UDP-N-Acetyl-D-mannosaminouronate + Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate > Hydrogen ion + Uridine 5'-diphosphate + Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronate dTDP-4-Acetamido-4,6-dideoxy-D-galactose + Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronate > dTDP + Hydrogen ion + Undecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactose N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol + UDP-ManNAcA > Uridine 5'-diphosphate + Hydrogen ion + Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate + Uridine 5'-diphosphate + Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronate Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate + TDP-Fuc4NAc + Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronate > Hydrogen ion + dTDP + Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate + Undecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactose 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 PW000959 Secondary Metabolites: enterobacterial common antigen biosynthesis 2 PW002045 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 splash10-01ox-0009000000-1f3ff0dd99f358e14841 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03dl-0009000100-98367624b9acfda19b76 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-006x-3119100710-f9989d9a1302a391f394 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0f6x-2609000000-1b26b0e059d997c76b71 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00y3-9201000000-b683817c4019f3260bef View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-08iv-9500000000-3d93a55212f860b03c8a View in MoNA
References
References:	Gerard, F., Brooks, M. A., Barreteau, H., Touze, T., Graille, M., Bouhss, A., Blanot, D., van Tilbeurgh, H., Mengin-Lecreulx, D. (2011). "X-ray structure and site-directed mutagenesis analysis of the Escherichia coli colicin M immunity protein." J Bacteriol 193:205-214. Pubmed: 21037007 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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 61495 HMDB ID Not Available Pubchem Compound ID 44229184 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID C55-PP-GLCNAC-MANNACA EcoCyc ID C55-PP-GLCNAC-MANNACA

Enzymes