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Record Information
Version	2.0
Creation Date	2012-05-31 14:33:01 -0600
Update Date	2015-06-03 17:19:32 -0600
Secondary Accession Numbers	ECMDB20204
Identification
Name:	UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine
Description	UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine is a member of the chemical class known as Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. It is a key component of peptidoglycan synthesis. The peptidoglycan synthesis pathway starts at 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-alpha-D-glucosamine, yielding the complete monomeric unit a lipid , also known as lipid . This final lipid intermediate is transferred 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.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa6f1ca88> Close
Synonyms:	UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate- D-alanyl-D-alanine UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate- D-alanyl-D-alanine UDP-n-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioic acid- D-alanyl-D-alanine UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioic acid- D-alanyl-D-alanine UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine
Chemical Formula:	C41H65N9O28P2
Weight:	Average: 1193.9458 Monoisotopic: 1193.341425565
InChI Key:	IMWOXEZVYQDRDF-XEJSTGJBSA-N
InChI:	InChI=1S/C41H65N9O28P2/c1-15(32(58)45-17(3)37(62)63)44-35(61)21(8-6-7-20(42)38(64)65)47-25(53)10-9-22(39(66)67)48-33(59)16(2)43-34(60)18(4)74-31-27(46-19(5)52)40(76-23(13-51)29(31)56)77-80(71,72)78-79(69,70)73-14-24-28(55)30(57)36(75-24)50-12-11-26(54)49-41(50)68/h11-12,15-18,20-24,27-31,36,40,51,55-57H,6-10,13-14,42H2,1-5H3,(H,43,60)(H,44,61)(H,45,58)(H,46,52)(H,47,53)(H,48,59)(H,62,63)(H,64,65)(H,66,67)(H,69,70)(H,71,72)(H,49,54,68)/t15-,16+,17?,18?,20?,21+,22-,23-,24-,27-,28-,29-,30-,31-,36-,40-/m1/s1
CAS number:	Not Available
IUPAC Name:	(6S)-2-amino-6-{[(4R)-4-carboxy-4-{[(2S)-2-[(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}-1-hydroxypropylidene)amino]-1-hydroxypropylidene]amino}-1-hydroxybutylidene]amino}-6-{[(1R)-1-[(1-carboxyethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}hexanoic acid
Traditional IUPAC Name:	(6S)-2-amino-6-{[(4R)-4-carboxy-4-{[(2S)-2-[(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}-1-hydroxypropylidene)amino]-1-hydroxypropylidene]amino}-1-hydroxybutylidene]amino}-6-{[(1R)-1-[(1-carboxyethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}hexanoic acid
SMILES:	[H]C(N)(CCC[C@]([H])(N=C(O)CC[C@@]([H])(N=C(O)[C@]([H])(C)N=C(O)C([H])(C)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC(O)=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(C)O)C(O)=O)C(O)=N[C@]([H])(C)C(O)=NC([H])(C)C(O)=O)C(O)=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	Pyrimidine ribonucleoside diphosphates Peptides Pentose phosphates N-acyl-alpha-hexosamines N-acyl-alpha amino acids Glycosylamines Alanine and derivatives Organic pyrophosphates Monosaccharide phosphates Alpha amino acids Tricarboxylic acids and derivatives Pyrimidones Monoalkyl phosphates Hydroxypyrimidines Oxanes Hydropyrimidines Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Amino acids Propargyl-type 1,3-dipolar organic compounds Oxacyclic compounds Dialkyl ethers Carboxylic acids Carboximidic acids Azacyclic compounds Primary alcohols Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
Substituents	Pyrimidine nucleotide sugar Pyrimidine ribonucleoside diphosphate Alpha peptide Pentose-5-phosphate Pentose phosphate N-acyl-alpha-hexosamine N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid Alanine or derivatives N-glycosyl compound Glycosyl compound Organic pyrophosphate Monosaccharide phosphate Alpha-amino acid or derivatives Alpha-amino acid Tricarboxylic acid or derivatives Hydroxypyrimidine Monoalkyl phosphate Pyrimidone Alkyl phosphate Pyrimidine Phosphoric acid ester Oxane Organic phosphoric acid derivative Monosaccharide Hydropyrimidine Heteroaromatic compound Tetrahydrofuran Amino acid Secondary alcohol Amino acid or derivatives Oxacycle Azacycle Organoheterocyclic compound Organic 1,3-dipolar compound Propargyl-type 1,3-dipolar organic compound Ether Dialkyl ether Carboxylic acid Carboxylic acid derivative Carboximidic acid derivative Carboximidic acid Organic nitrogen compound Organic oxygen compound Organopnictogen compound Organic oxide Hydrocarbon derivative Primary amine Primary alcohol Organooxygen compound Organonitrogen compound Primary aliphatic amine Carbonyl group Amine Alcohol Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.28 g/L ALOGPS logP -0.4 ALOGPS logP -2.8 ChemAxon logS -3.6 ALOGPS pKa (Strongest Acidic) 1.72 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 33 ChemAxon Hydrogen Donor Count 17 ChemAxon Polar Surface Area 597.26 Ų ChemAxon Rotatable Bond Count 31 ChemAxon Refractivity 256.76 m³·mol⁻¹ ChemAxon Polarizability 108.74 ų 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:	D-Alanyl-D-alanine + Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate > ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine Undecaprenyl phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine > Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + Uridine 5'-monophosphate Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + D-Alanyl-D-alanine <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine + Di-trans,poly-cis-undecaprenyl phosphate <> Uridine 5'-monophosphate + Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine + Di-trans,poly-cis-undecaprenyl phosphate > N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimelyl-D-alanyl-D-alanine-diphosphoundecaprenol + Uridine 5'-monophosphate D-Alanyl-D-alanine + Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate > ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine D-Alanyl-D-alanine + Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate > ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine
SMPDB Pathways:	Lysine biosynthesis PW000771
KEGG Pathways:	Lysine biosynthesis ec00300 Peptidoglycan biosynthesis ec00550
EcoCyc Pathways:	UDP-N-acetylmuramoyl-pentapeptide biosynthesis III (meso-DAP-containing) PWY-6387 peptidoglycan biosynthesis I (meso-diaminopimelate containing) PEPTIDOGLYCANSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-03di-1900000000-043379bbab21aa37c1d9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03di-3900000100-3ff9ed2cfb53302e36f0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03di-6901100000-2aa0283bd4d6a4d45af7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03dl-5901100100-fa405314e19a562bcd9c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0233-4902001002-0af52ce7d9043bd0091d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-06tf-5913002000-0006797b37c53638ca0c View in MoNA MS Mass Spectrum (Electron Ionization) 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 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
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 23724482 Kegg ID C04882 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID C1 EcoCyc ID C1

Enzymes