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Record Information
Version	2.0
Creation Date	2012-10-10 12:18:48 -0600
Update Date	2015-06-03 17:26:01 -0600
Secondary Accession Numbers	ECMDB23145
Identification
Name:	UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diamino-heptanedioate
Description	UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diamino-heptanedioate is an intermediate in peptidoglycan synthesis. It is a substrate for UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--2,6-diaminopimelate ligase which catalyzes the addition of meso-diaminopimelic acid to the nucleotide precursor UDP-N-acetylmuramoyl-L-alanyl-D-glutamate (UMAG) in the biosynthesis of bacterial cell-wall peptidoglycan.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x504344b4> Close
Synonyms:	(2S,6R)-2-4-(2R)-2-(2R)-2-(2R,3R,4R,5S,6R)-3-acetamido-2-(2R,3S,4R,5R)-5-(2,4-Dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yloxypropanoylaminopropanoylamino-4-carboxybutanoylamino-6-aminoheptanedioate (2S,6R)-2-4-(2R)-2-(2R)-2-(2R,3R,4R,5S,6R)-3-acetamido-2-(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yloxypropanoylaminopropanoylamino-4-carboxybutanoylamino-6-aminoheptanedioic acid UDP-N-Acetylmuramoyl-L-alanyl-D-g-glutamyl-meso-2,6-diamino-heptanedioate UDP-N-Acetylmuramoyl-L-alanyl-D-g-glutamyl-meso-2,6-diamino-heptanedioic acid UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diamino-heptanedioate UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diamino-heptanedioic acid UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diamino-heptanedioate UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diamino-heptanedioic acid
Chemical Formula:	C35H55N7O26P2
Weight:	Average: 1051.79 Monoisotopic: 1051.267197991
InChI Key:	QUHLBZKCGUXHGP-YXVFMYSNSA-N
InChI:	InChI=1S/C35H55N7O26P2/c1-13(28(50)40-18(33(56)57)7-8-21(45)39-17(32(54)55)6-4-5-16(36)31(52)53)37-29(51)14(2)64-27-23(38-15(3)44)34(66-19(11-43)25(27)48)67-70(61,62)68-69(59,60)63-12-20-24(47)26(49)30(65-20)42-10-9-22(46)41-35(42)58/h9-10,13-14,16-20,23-27,30,34,43,47-49H,4-8,11-12,36H2,1-3H3,(H,37,51)(H,38,44)(H,39,45)(H,40,50)(H,52,53)(H,54,55)(H,56,57)(H,59,60)(H,61,62)(H,41,46,58)/t13-,14-,16-,17+,18?,19-,20-,23-,24-,25-,26-,27-,30-,34-/m1/s1
CAS number:	Not Available
IUPAC Name:	(2R,6S)-2-amino-6-{4-carboxy-4-[(2R)-2-[(2R)-2-{[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanamido]butanamido}heptanedioic acid
Traditional IUPAC Name:	(2R,6S)-2-amino-6-{4-carboxy-4-[(2R)-2-[(2R)-2-{[(2R,3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanamido]butanamido}heptanedioic acid
SMILES:	C[C@@H](NC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@@H]1NC(C)=O)C(=O)NC(CCC(=O)N[C@@H](CCC[C@@H](N)C(O)=O)C(O)=O)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as 3-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a 3-enoyl chain.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Fatty acyl thioesters
Direct Parent	3-enoyl CoAs
Alternative Parents	Acyl CoAs Coenzyme A and derivatives Purine ribonucleoside diphosphates Ribonucleoside 3'-phosphates Pentose phosphates Beta amino acids and derivatives Glycosylamines 6-aminopurines Monosaccharide phosphates Organic pyrophosphates Aminopyrimidines and derivatives Monoalkyl phosphates Imidolactams N-acyl amines N-substituted imidazoles Heteroaromatic compounds Tetrahydrofurans Thioesters Secondary alcohols Carbothioic S-esters Secondary carboxylic acid amides Oxacyclic compounds Azacyclic compounds Sulfenyl compounds Organopnictogen compounds Hydrocarbon derivatives Primary amines Carbonyl compounds Organic oxides
Substituents	Coenzyme a or derivatives Purine ribonucleoside 3',5'-bisphosphate Purine ribonucleoside bisphosphate Purine ribonucleoside diphosphate Ribonucleoside 3'-phosphate Pentose phosphate Pentose-5-phosphate Beta amino acid or derivatives Glycosyl compound N-glycosyl compound 6-aminopurine Monosaccharide phosphate Organic pyrophosphate Pentose monosaccharide Imidazopyrimidine Purine Monoalkyl phosphate Aminopyrimidine Imidolactam N-acyl-amine N-substituted imidazole Organic phosphoric acid derivative Monosaccharide Pyrimidine Alkyl phosphate Fatty amide Phosphoric acid ester Tetrahydrofuran Imidazole Azole Heteroaromatic compound Carbothioic s-ester Secondary alcohol Thiocarboxylic acid ester Carboxamide group Secondary carboxylic acid amide Amino acid or derivatives Sulfenyl compound Thiocarboxylic acid or derivatives Organoheterocyclic compound Azacycle Oxacycle Carboxylic acid derivative Organosulfur compound Organic oxygen compound Hydrocarbon derivative Carbonyl group Organic nitrogen compound Primary amine Organopnictogen compound Organic oxide Organooxygen compound Organonitrogen compound Alcohol Amine Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	Fatty acyl CoAs (LMFA07050009 )
Physical Properties
State:	Not Available
Charge:	-4
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 6.03 g/L ALOGPS logP -0.67 ALOGPS logP -8.6 ChemAxon logS -2.2 ALOGPS pKa (Strongest Acidic) 1.5 ChemAxon pKa (Strongest Basic) 9.3 ChemAxon Physiological Charge -4 ChemAxon Hydrogen Acceptor Count 24 ChemAxon Hydrogen Donor Count 15 ChemAxon Polar Surface Area 514.63 Ų ChemAxon Rotatable Bond Count 27 ChemAxon Refractivity 218.71 m³·mol⁻¹ ChemAxon Polarizability 94.79 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-3901000000-d535f4793be83c6d5099 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03di-2901000100-66b97259fb546096ec79 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03di-5901000000-29ed96bdf1f795ecf89c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0w33-9202102002-1302dbbe820b7881209a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001l-9405000220-8c5ac05b0cc0ec46dd6f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-06tf-4914000000-3bb1bca4a729e85bb941 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:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 28639 HMDB ID Not Available Pubchem Compound ID 53297336 Kegg ID C04877 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available