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Record Information
Version	2.0
Creation Date	2012-07-30 14:55:08 -0600
Update Date	2015-06-03 17:21:01 -0600
Secondary Accession Numbers	ECMDB21257
Identification
Name:	O16 antigen undecaprenyl diphosphate
Description	O16 antigen undecaprenyl diphosphate is a member of the chemical class known as Polyprenols. These are prenols with more than 4 consecutive isoprene units. O16 antigen is a repetitive glycan polymer contained within an LPS. It is also called O polysaccharide, or O side-chain of the bacteria. The O antigen is attached to the core oligosaccharide, and comprises the outermost domain of the LPS molecule. The composition of the O chain varies from strain to strain. For example, there are over 160 different O antigen structures produced by different E. coli strains.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xafcd03ac> Close
Synonyms:	O16 Antigen undecaprenyl diphosphoric acid
Chemical Formula:	C89H145NO32P2
Weight:	Average: 1803.0386 Monoisotopic: 1801.922494573
InChI Key:	NYDKXESIKHJNQU-FIYHCCFRSA-L
InChI:	InChI=1S/C89H147NO32P2/c1-52(2)26-16-27-53(3)28-17-29-54(4)30-18-31-55(5)32-19-33-56(6)34-20-35-57(7)36-21-37-58(8)38-22-39-59(9)40-23-41-60(10)42-24-43-61(11)44-25-45-62(12)46-47-112-123(106,107)122-124(108,109)121-85-70(90-64(14)93)82(74(99)69(116-85)51-110-86-78(103)75(100)72(97)67(49-92)115-86)119-89-84(114-65(15)94)83(71(96)63(13)113-89)120-88-79(104)76(101)73(98)68(117-88)50-111-87-80(105)77(102)81(118-87)66(95)48-91/h26,28,30,32,34,36,38,40,42,44,46,63,66-89,91-92,95-105H,16-25,27,29,31,33,35,37,39,41,43,45,47-51H2,1-15H3,(H,90,93)(H,106,107)(H,108,109)/p-2/b53-28+,54-30+,55-32-,56-34-,57-36-,58-38-,59-40-,60-42-,61-44-,62-46-
CAS number:	Not Available
IUPAC Name:	N-(4-{[3-(acetyloxy)-4-{[6-({[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5-hydroxy-6-methyloxan-2-yl]oxy}-5-hydroxy-2-{[hydroxy({[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,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 phosphonato]oxy})phosphoryl]oxy}-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl)ethanecarboximidate
Traditional IUPAC Name:	N-(4-{[3-(acetyloxy)-4-{[6-({[5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5-hydroxy-6-methyloxan-2-yl]oxy}-5-hydroxy-2-({hydroxy[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,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 phosphonato]oxyphosphoryl}oxy)-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl)ethanecarboximidate
SMILES:	[H]\C(CC\C(C)=C(/[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])COP([O-])(=O)OP(O)(=O)OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(OC2OC(C)C(O)C(OC3OC(COC4OC(C(O)CO)C(O)C4O)C(O)C(O)C3O)C2OC(C)=O)C1N=C(C)[O-])=C(\C)CCC=C(C)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 Oligosaccharide phosphates Polyprenyl monophosphates N-acyl-alpha-hexosamines O-glycosyl compounds Organic pyrophosphates Isoprenoid phosphates Oxanes Alkyl phosphates Tetrahydrofurans Acetamides Secondary carboxylic acid amides Secondary alcohols Carboxylic acid esters Polyols Oxacyclic compounds Monocarboxylic acids and derivatives Acetals Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds Organic anions
Substituents	Polyterpenoid Bactoprenol diphosphate Polyprenyl phospho carbohydrate Oligosaccharide phosphate Polyprenyl monophosphate Oligosaccharide Polyprenyl phosphate skeleton N-acyl-alpha-hexosamine O-glycosyl compound Glycosyl compound Organic pyrophosphate Isoprenoid phosphate Alkyl phosphate Phosphoric acid ester Oxane Organic phosphoric acid derivative Acetamide Tetrahydrofuran Secondary carboxylic acid amide Secondary alcohol Carboxylic acid ester Carboxamide group Oxacycle Organoheterocyclic compound Polyol Monocarboxylic acid or derivatives Carboxylic acid derivative 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:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.013 g/L ALOGPS logP 5.64 ALOGPS logP 9.79 ChemAxon logS -5.2 ALOGPS pKa (Strongest Acidic) 1.73 ChemAxon pKa (Strongest Basic) -3.7 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 29 ChemAxon Hydrogen Donor Count 14 ChemAxon Polar Surface Area 512.9 Ų ChemAxon Rotatable Bond Count 53 ChemAxon Refractivity 477.61 m³·mol⁻¹ ChemAxon Polarizability 190.31 ų ChemAxon Number of Rings 5 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:	(O16 antigen)x2 undecaprenyl diphosphate + O16 antigen undecaprenyl diphosphate > Hydrogen ion + (O16 antigen)x3 undecaprenyl diphosphate + Undecaprenyl diphosphate (O16 antigen)x3 undecaprenyl diphosphate + O16 antigen undecaprenyl diphosphate > Hydrogen ion + (O16 antigen)x4 undecaprenyl diphosphate + Undecaprenyl diphosphate 2 O16 antigen undecaprenyl diphosphate > Hydrogen ion + (O16 antigen)x2 undecaprenyl diphosphate + Undecaprenyl diphosphate
SMPDB Pathways:	Lipopolysaccharide biosynthesis PW000831
KEGG Pathways:	Lipopolysaccharide biosynthesis ec00540
EcoCyc Pathways:	superpathway of lipopolysaccharide biosynthesis LPSSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0wmi-3300000090-6ff3b2c5c6214ff3691f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00kb-4401000890-2ddfe4803a601e34f330 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0c03-9301000010-616a951c4a4c9ac95167 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0r00-9540000050-7932bd59bb435a3df244 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0bt9-9710000010-1e241284b41bfcd113df View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-9110000000-6b3d5c80d622bf1ca54c View in MoNA
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
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 Not Available Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID CPD0-2279 EcoCyc ID CPD0-2279

Enzymes

Transporters