UDP-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysine (PAMDB120102)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120102
Identification
Name: UDP-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysine
Description:Glutamyl-L-lysine is a dipeptide whose absorption is facilitated by the human intestinal oligopeptide transporter (PEPT1) (PMID 16759105 ). Glutamyl-L-lysine is an isopeptides found in human hair. ( Schriftenreihe des Deutschen Wollforschungsinstitutes (Technische Hochschule Aachen) (1979), (Sonderband, Haarwiss. Symp. Dtsch. Wollforschungsinst., 1st, 1978), 128-30. ).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • UDP-N-acetylmuramoyl-L-alanyl-alpha-D-glutamyl-L-lysine
  • UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysine
Chemical Formula: C34H52N7O24P2
Average Molecular Weight: 1004.765
Monoisotopic Molecular Weight: 1008.2852
InChI Key: WXBLSQNZKMJACT-BYEZXYKXSA-K
InChI:InChI=1S/C34H55N7O24P2/c1-14(28(49)39-18(32(53)54)7-8-21(44)38-17(31(51)52)6-4-5-10-35)36-29(50)15(2)61-27-23(37-16(3)43)33(63-19(12-42)25(27)47)64-67(58,59)65-66(56,57)60-13-20-24(46)26(48)30(62-20)41-11-9-22(45)40-34(41)55/h9,11,14-15,17-20,23-27,30,33,42,46-48H,4-8,10,12-13,35H2,1-3H3,(H,36,50)(H,37,43)(H,38,44)(H,39,49)(H,51,52)(H,53,54)(H,56,57)(H,58,59)(H,40,45,55)/p-3/t14-,15+,17-,18+,19+,20+,23+,24+,25+,26+,27+,30+,33+/m0/s1
CAS number: 5891-53-2
IUPAC Name:(2S)-6-amino-2-[(2S)-2-amino-4-carboxybutanamido]hexanoic acid
Traditional IUPAC Name: L-?-glutamyl-L-lysine
SMILES:CC(NC(=O)C(C)OC3(C(O)C(CO)OC(OP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N2(C=CC(=O)NC(=O)2)))C(NC(C)=O)3))C(=O)NC(CCC(NC(CCCC[N+])C(=O)[O-])=O)C([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct Parent Dipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Glutamic acid or derivatives
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Medium-chain fatty acid
  • Amino fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Fatty acid
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid salt
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Organic salt
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Amine
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic zwitterion
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.13 mg/mLALOGPS
logP-3.9ALOGPS
logP-6.1ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.33ChemAxon
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.74 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity65.9 m3·mol-1ChemAxon
Polarizability28.3 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
UDP-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysine + D-Alanyl-D-alanine + ATP → Hydrogen ion + UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine + phosphate + ADP
Pathways: Not Available
Spectra
Spectra: Not Available
References
References:
  • Jeitner TM, Bogdanov MB, Matson WR, Daikhin Y, Yudkoff M, Folk JE, Steinman L, Browne SE, Beal MF, Blass JP, Cooper AJ: N(epsilon)-(gamma-L-glutamyl)-L-lysine (GGEL) is increased in cerebrospinal fluid of patients with Huntington's disease. J Neurochem. 2001 Dec;79(5):1109-12. [11739625 ]
  • Vig BS, Stouch TR, Timoszyk JK, Quan Y, Wall DA, Smith RL, Faria TN: Human PEPT1 pharmacophore distinguishes between dipeptide transport and binding. J Med Chem. 2006 Jun 15;49(12):3636-44. [16759105 ]
Synthesis Reference: Khosla, M. C.; Anand, Nitya. Synthesis of Na-(a-glutamyl and aspartyl)lysines. Journal of Scientific and Industrial Research, Section B: Physical Sciences (1962), 21B 287-9.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
HMDBHMDB04207
CHEBI9837
PUBCHEM46173306
LIGAND-CPDC04700