UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate (PAMDB001049)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001049
Identification
Name: UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate
Description:UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate is a peptide. 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-D-glucosamine, yielding the complete monomeric unit a lipid II, also known as lipid II. 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
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • UDP-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-diaminopimelate
  • UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate
  • UDP-MurNAc-L-Ala-D-Glu-meso-A2pm
  • UDP-MurNAc-L-Ala-D-Glu-meso-A2pm
  • UDP-n-Acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-diaminopimelate
  • UDP-n-Acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-diaminopimelic acid
  • UDP-N-acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelate
  • UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelate
  • UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelic acid
  • UDP-N-Acetylmuramoyl-L-alanyl-D-g-glutamyl-meso-2,6-diaminopimelate
  • UDP-N-Acetylmuramoyl-L-alanyl-D-g-glutamyl-meso-2,6-diaminopimelic acid
  • UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelic acid
  • UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate
  • UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioic acid
  • UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelate
  • UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelic acid
  • UDP-N-Acetylmuramoyl-L-alanyl-g-D-glutamyl-meso-diaminopimelate
  • UDP-N-Acetylmuramoyl-L-alanyl-g-D-glutamyl-meso-diaminopimelic acid
  • UDP-N-Acetylmuramoyl-L-alanyl-gamma-D-glutamyl-meso-diaminopimelate
  • UDP-N-Acetylmuramoyl-L-alanyl-gamma-D-glutamyl-meso-diaminopimelic acid
  • UDP-N-Acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-diaminopimelate
  • UDP-N-Acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-diaminopimelic acid
Chemical Formula: C35H55N7O26P2
Average Molecular Weight: 1051.79
Monoisotopic Molecular Weight: 1051.267197991
InChI Key: QUHLBZKCGUXHGP-IBSIGGROSA-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+/m0/s1
CAS number: Not Available
IUPAC Name: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}heptanedioic acid
Traditional IUPAC Name: 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}heptanedioic acid
SMILES:[H]C(N)(CCCC([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)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound 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 ClassNucleosides, nucleotides, and analogues
Class Pyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct Parent Pyrimidine nucleotide sugars
Alternative Parents
Substituents
  • Pyrimidine nucleotide sugar
  • Pyrimidine ribonucleoside diphosphate
  • Alpha peptide
  • Saccharolipid
  • N-acyl-alpha-hexosamine
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Glucosamine
  • Amino sugar
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Amino saccharide
  • Pyrimidone
  • Amino fatty acid
  • Fatty acyl
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydropyrimidine
  • Heteroaromatic compound
  • Oxolane
  • Secondary alcohol
  • 1,2-diol
  • 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
  • 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:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.08 mg/mLALOGPS
logP-0.71ALOGPS
logP-3.4ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count29ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area532.08 Å2ChemAxon
Rotatable Bond Count27ChemAxon
Refractivity221.12 m3·mol-1ChemAxon
Polarizability94.84 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + Meso-2,6-Diaminoheptanedioate + Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate > Adenosine diphosphate + Phosphate + Hydrogen ion + UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate + ADP
UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate + D-Alanyl-D-alanine + Adenosine triphosphate > Adenosine diphosphate + Phosphate + Hydrogen ion + UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + ADP
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3902000000-768b4205c31ec38d912dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2902000100-52dd4e66fad9a96a043dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-2902000000-64773990e7770fc9b147View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0il3-9401202002-b84c4eb76b090b642d65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01qc-9504110220-9967e6e46a6cd500f0f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-4913110000-75ad36f025dc10e827eeView 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
External Links:
ResourceLink
CHEBI ID28639
HMDB IDNot Available
Pubchem Compound ID23724481
Kegg IDC04877
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDUDP-AAGM-DIAMINOHEPTANEDIOATE
EcoCyc IDUDP-AAGM-DIAMINOHEPTANEDIOATE