Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001376
Identification
Name: L-Ala-D-Glu-meso-A2pm
Description:L-ala-D-glu-meso-a2pm 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.
Structure
Thumb
Synonyms:
  • L-ALA-D-GLU-MESOA2PM
Chemical Formula: C15H26N4O8
Average Molecular Weight: 390.3889
Monoisotopic Molecular Weight: 390.175063828
InChI Key: FMNCPUGORYYCEM-QCLAVDOMSA-N
InChI:InChI=1S/C15H26N4O8/c1-7(16)12(21)19-10(15(26)27)5-6-11(20)18-9(14(24)25)4-2-3-8(17)13(22)23/h7-10H,2-6,16-17H2,1H3,(H,18,20)(H,19,21)(H,22,23)(H,24,25)(H,26,27)/t7-,8+,9-,10+/m0/s1
CAS number: Not Available
IUPAC Name:(2R,6S)-2-amino-6-{[(4R)-4-{[(2S)-2-amino-1-hydroxypropylidene]amino}-4-carboxy-1-hydroxybutylidene]amino}heptanedioic acid
Traditional IUPAC Name: (2R,6S)-2-amino-6-{[(4R)-4-{[(2S)-2-amino-1-hydroxypropylidene]amino}-4-carboxy-1-hydroxybutylidene]amino}heptanedioic acid
SMILES:[H][C@@](C)(N)C(O)=N[C@]([H])(CCC(O)=N[C@@]([H])(CCC[C@@]([H])(N)C(O)=O)C(O)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds 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.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent Peptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • D-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Amino fatty acid
  • Fatty acyl
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.266 mg/mLALOGPS
logP-3.7ALOGPS
logP-5.7ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)1.91ChemAxon
pKa (Strongest Basic)9.85ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area229.12 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity90.07 m3·mol-1ChemAxon
Polarizability37.83 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0075-1319000000-371d1ce680638f44cbd4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-8956000000-e2de0460cf1623e1c85dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-2921000000-3e663d34afe0abfe9531View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-0009000000-d1deed39f56f0af68f71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00g0-2229000000-eb11aac087d2dc2237ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007c-8911000000-ce2d49e3f2972f6db36aView in MoNA
References
References:
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID25203562
Kegg IDNot Available
ChemSpider ID26325831
Wikipedia IDNot Available
BioCyc IDL-ALA-D-GLU-MESOA2PM
EcoCyc IDL-ALA-D-GLU-MESOA2PM
Ligand ExpoMHI

Enzymes

General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for dipeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
dppB
Locus Tag:
PA4503
Molecular weight:
37 kDa
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for dipeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
dppC
Locus Tag:
PA4504
Molecular weight:
32.4 kDa
General function:
Involved in ATP binding
Specific function:
Reutilizes the intact tripeptide L-alanyl-gamma-D- glutamyl-meso-diaminopimelate by linking it to UDP-N-acetylmuramic acid
Gene Name:
mpl
Locus Tag:
PA4020
Molecular weight:
48.5 kDa

Transporters

General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for dipeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
dppB
Locus Tag:
PA4503
Molecular weight:
37 kDa
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for dipeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
dppC
Locus Tag:
PA4504
Molecular weight:
32.4 kDa