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Record Information
Version	2.0
Creation Date	2012-10-10 12:18:33 -0600
Update Date	2015-06-03 17:26:00 -0600
Secondary Accession Numbers	ECMDB23139
Identification
Name:	UDP-N-Acetylmuramoyl-L-alanyl-gamma-D-glutamyl-L-lysyl-D-alanyl-D-alanine
Description	UDP-N-Acetylmuramoyl-L-alanyl-gamma-D-glutamyl-L-lysyl-D-alanyl-D-alanine is an intermediate in peptidoglycan biosynthesis. It is a substrate for the enzyme UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase which catalyzes the final step in the synthesis of UDP-N-acetylmuramoyl-pentapeptide, the precursor of murein.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xae6b2e08> Close
Synonyms:	UDP-N-Acetylmuramoyl-L-alanyl-g-D-glutamyl-L-lysyl-D-alanyl-D-alanine UDP-N-Acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine
Chemical Formula:	C40H65N9O26P2
Weight:	Average: 1149.9363 Monoisotopic: 1149.351596321
InChI Key:	PFMVORMCVGOQKR-MZSDELDXSA-N
InChI:	InChI=1S/C40H65N9O26P2/c1-16(32(57)44-18(3)37(61)62)43-35(60)21(8-6-7-12-41)46-25(52)10-9-22(38(63)64)47-33(58)17(2)42-34(59)19(4)71-31-27(45-20(5)51)39(73-23(14-50)29(31)55)74-77(68,69)75-76(66,67)70-15-24-28(54)30(56)36(72-24)49-13-11-26(53)48-40(49)65/h11,13,16-19,21-24,27-31,36,39,50,54-56H,6-10,12,14-15,41H2,1-5H3,(H,42,59)(H,43,60)(H,44,57)(H,45,51)(H,46,52)(H,47,58)(H,61,62)(H,63,64)(H,66,67)(H,68,69)(H,48,53,65)/t16-,17-,18+,19+,21-,22-,23+,24+,27+,28+,29+,30+,31+,36+,39+/m0/s1
CAS number:	Not Available
IUPAC Name:	(2S)-4-{[(1S)-5-amino-1-{[(1S)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}pentyl]-C-hydroxycarbonimidoyl}-2-{[(2S)-2-{[(2R)-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}butanoic acid
Traditional IUPAC Name:	(2S)-4-{[(1S)-5-amino-1-{[(1S)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}pentyl]-C-hydroxycarbonimidoyl}-2-{[(2S)-2-{[(2R)-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}butanoic acid
SMILES:	[H][C@](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)=N[C@@]([H])(C)C(O)=N[C@@]([H])(CCC(O)=N[C@@]([H])(CCCCN)C(O)=N[C@@]([H])(C)C(O)=N[C@]([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 Pyrimidones Monoalkyl phosphates Hydroxypyrimidines Oxanes Hydropyrimidines Dicarboxylic acids and derivatives 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 Hydroxypyrimidine Monoalkyl phosphate Pyrimidone Alkyl phosphate Pyrimidine Phosphoric acid ester Oxane Organic phosphoric acid derivative Monosaccharide Hydropyrimidine Dicarboxylic acid or derivatives 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 0.2 g/L ALOGPS logP -0.38 ALOGPS logP -3.7 ChemAxon logS -3.8 ALOGPS pKa (Strongest Acidic) 1.71 ChemAxon pKa (Strongest Basic) 10.21 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 31 ChemAxon Hydrogen Donor Count 16 ChemAxon Polar Surface Area 559.96 Ų ChemAxon Rotatable Bond Count 30 ChemAxon Refractivity 250.93 m³·mol⁻¹ ChemAxon Polarizability 106.38 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:
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 splash10-03di-1900100000-ca60f48eab121e478fd8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03di-3900000100-5f1cabf69b348c6629aa View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03di-6921100001-9b4fc4ff9dae58b61f10 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03e9-5901100100-e2f2c32dccc7d77d95a4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001l-4903100002-39705f2f3e29d8e03294 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0bvl-4913011000-3d8817522bb28cc942c2 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 46173210 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available