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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	ECMDB21256
Identification
Name:	O-Acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate
Description	O-acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate is an intermediate in peptidoglycan synthesis. Peptidoglycan can be described as a fisherman's net that encloses bacteria. The mesh of the net is made of two segments of parallel, somewhat inextensible glycan threads, held together by two small elastic peptide crosslinks allowing the net to expand or shrink. The glycan moiety of the peptidoglycan is very uniform among all bacteria, and is made up of alternating β-1,4-linked N-acetylglucosamine and N-acetyl muramate residues, with an average chain lengthof 10 to 65 disaccharide units (depending on the organism). The peptidoglycan synthesis pathway starts in the cytoplasm, where in six steps the peptidoglycan precursor a UDP-N-acetylmuramoyl-pentapeptide is synthesized. This precursor is then attached to the memberane acceptor all-trans-undecaprenyl phosphate, generating a N-acetylmuramoyl-pentapeptide-diphosphoundecaprenol, also known as lipid I. Another transferase then adds UDP-N-acetyl-α-D-glucosamine, yielding the complete monomeric unit a lipid II, also known as lipid II. This final lipid intermediate is transferred by an as yet unknown mechanism through the membrane. The peptidoglycan monomers are then polymerized on the outside surface by glycosyltransferases, which form the linear glycan chains, and transpeptidases, which catalyze the formation of peptide crosslinks. Peptide crosslinks form between different parts of the peptides depending on the organism. For example, in Mycobacteria and in E. coli most links form between the carboxyl group of the penultimate D-alanine (residue 4) of one peptide to the amino group at the D-center of meso-diaminopimelate (residue 3) of an adjacent peptide of a second glycan chain (as in E. coli). The crosslinking reaction is catalyzed by transpeptidases and involves the cleavage of the D-alanyl-D-alanine bond of the donor peptide, providing the energy to drive the reaction. As a result, the peptides in the peptidoglycan polymers are one or two amino acids shorter than the peptides in the monomers.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xae4d7700> Close
Synonyms:	O-acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate O-Acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphoric acid
Chemical Formula:	C71H115NO17P2
Weight:	Average: 1316.6168 Monoisotopic: 1315.764024283
InChI Key:	WYHMIVUCEAXZMZ-LRILUZMESA-L
InChI:	InChI=1S/C71H117NO17P2/c1-49(2)26-16-27-50(3)28-17-29-51(4)30-18-31-52(5)32-19-33-53(6)34-20-35-54(7)36-21-37-55(8)38-22-39-56(9)40-23-41-57(10)42-24-43-58(11)44-25-45-59(12)46-47-83-90(79,80)89-91(81,82)88-70-64(72-61(14)74)68(66(77)63(48-73)86-70)87-71-69(85-62(15)75)67(78)65(76)60(13)84-71/h26,28,30,32,34,36,38,40,42,44,46,60,63-71,73,76-78H,16-25,27,29,31,33,35,37,39,41,43,45,47-48H2,1-15H3,(H,72,74)(H,79,80)(H,81,82)/p-2/b50-28+,51-30+,52-32+,53-34+,54-36+,55-38+,56-40+,57-42+,58-44+,59-46+
CAS number:	Not Available
IUPAC Name:	N-(4-{[3-(acetyloxy)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-5-hydroxy-2-{[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 phosphonato]oxy})phosphoryl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanecarboximidate
Traditional IUPAC Name:	N-(4-{[3-(acetyloxy)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-5-hydroxy-2-({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 phosphonato]oxyphosphoryl}oxy)-6-(hydroxymethyl)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(CO)C(O)C(OC2OC(C)C(O)C(O)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 Polyprenyl monophosphates N-acyl-alpha-hexosamines Disaccharide phosphates O-glycosyl compounds Organic pyrophosphates Isoprenoid phosphates Oxanes Alkyl phosphates Acetamides Secondary carboxylic acid amides Secondary alcohols Carboxylic acid esters 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 Polyprenyl monophosphate Polyprenyl phosphate skeleton N-acyl-alpha-hexosamine Disaccharide phosphate O-glycosyl compound Glycosyl compound Disaccharide Organic pyrophosphate Isoprenoid phosphate Alkyl phosphate Phosphoric acid ester Oxane Organic phosphoric acid derivative Acetamide Secondary carboxylic acid amide Secondary alcohol Carboxylic acid ester Carboxamide group Oxacycle Organoheterocyclic compound 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:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.0005 g/L ALOGPS logP 7.71 ALOGPS logP 14.54 ChemAxon logS -6.4 ALOGPS pKa (Strongest Acidic) 1.87 ChemAxon pKa (Strongest Basic) 1.18 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 14 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 275.45 Ų ChemAxon Rotatable Bond Count 43 ChemAxon Refractivity 380.37 m³·mol⁻¹ ChemAxon Polarizability 150.46 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:	O-Acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate + UDP-Glucose > Glucosyl-O-acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate + Hydrogen ion + Uridine 5'-diphosphate Acetyl-CoA + Rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate > O-Acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate + Coenzyme A
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-014i-2009000000-62f824512033aaf00aa4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-01q9-2109000100-aade96ab11002661f56d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-01vo-9413000200-e1ce742ceaf03059975f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0bt9-9016000000-424ba6a90892708a14cf View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0a4i-9001000000-8a6e32c88ea68bc7ed3e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-9000000000-81555154edd536dba74a View in MoNA
References
References:	Not Available
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 46173140 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID CPD0-2290 EcoCyc ID CPD0-2290

Enzymes