Record Information
Version2.0
Creation Date2012-07-30 14:55:05 -0600
Update Date2015-06-03 17:20:58 -0600
Secondary Accession Numbers
  • ECMDB21240
Identification
Name:L-alanine-D-glutamate-meso-2,6-diaminoheptanedioate
DescriptionL-alanine-d-glutamate-meso-2,6-diaminoheptanedioate belongs to the class of 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. (inferred from compound structure)
Structure
Thumb
Synonyms:
  • L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioic acid
  • L-Alanine-D-glutamic acid-meso-2,6-diaminoheptanedioic acid
Chemical Formula:C18H31N5O9
Weight:Average: 461.4668
Monoisotopic: 461.212177615
InChI Key:BAPAFFOXTCMVCC-UHFFFAOYSA-N
InChI:InChI=1S/C18H31N5O9/c1-8(19)14(25)22-11(17(29)30)5-3-4-10(16(27)28)21-13(24)7-6-12(18(31)32)23-15(26)9(2)20/h8-12H,3-7,19-20H2,1-2H3,(H,21,24)(H,22,25)(H,23,26)(H,27,28)(H,29,30)(H,31,32)
CAS number:Not Available
IUPAC Name:2-[(2-amino-1-hydroxypropylidene)amino]-6-({4-[(2-amino-1-hydroxypropylidene)amino]-4-carboxy-1-hydroxybutylidene}amino)heptanedioic acid
Traditional IUPAC Name:2-[(2-amino-1-hydroxypropylidene)amino]-6-({4-[(2-amino-1-hydroxypropylidene)amino]-4-carboxy-1-hydroxybutylidene}amino)heptanedioic acid
SMILES:CC(N)C(O)=NC(CCCC(N=C(O)CCC(N=C(O)C(C)N)C(O)=O)C(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Gamma-glutamyl alpha-amino acid
  • Glutamine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • Alanine or derivatives
  • Alpha-amino acid or derivatives
  • Tricarboxylic acid or derivatives
  • N-acyl-amine
  • Fatty acyl
  • Fatty amide
  • Carboxylic acid salt
  • Secondary carboxylic acid amide
  • Amino acid
  • Carboxamide group
  • Amino acid or derivatives
  • Carboxylic acid
  • Organooxygen compound
  • Primary amine
  • Primary aliphatic amine
  • Organic zwitterion
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP-3.4ALOGPS
logP-5.4ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.09ChemAxon
pKa (Strongest Basic)9.87ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area261.71 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity107.89 m³·mol⁻¹ChemAxon
Polarizability45.04 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_6_40) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-1046900000-8426fa1b8b51ee154716View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-8249100000-997556b0351da0c5a0ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02gc-2639000000-2245ec94b27468843986View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xu-0014900000-38722628f23ead5b489cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dm-2029500000-29c2f1849c59dd022979View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0076-9557000000-6d7f5643e4c278c62f76View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID46173126
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:
Cell-wall hydrolase probably involved in cell-wall hydrolysis, septation or recycling
Gene Name:
amiB
Uniprot ID:
P26365
Molecular weight:
47985
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.
General function:
Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides
Gene Name:
amiA
Uniprot ID:
P36548
Molecular weight:
31412
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.
General function:
Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:
Cell-wall hydrolase probably involved in cell-wall hydrolysis, septation or recycling
Gene Name:
amiC
Uniprot ID:
P63883
Molecular weight:
45634
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.
General function:
Defense mechanisms
Specific function:
Releases the terminal D-alanine residue from the cytoplasmic tetrapeptide recycling product L-Ala-gamma-D-Glu-meso- Dap-D-Ala. To a lesser extent, can also cleave D-Ala from murein derivatives containing the tetrapeptide, i.e. MurNAc-tetrapeptide, UDP-MurNAc-tetrapeptide, GlcNAc-MurNAc-tetrapeptide, and GlcNAc- anhMurNAc-tetrapeptide. Does not act on murein sacculi or cross- linked muropeptides. The tripeptides produced by the lcdA reaction can then be reused as peptidoglycan building blocks; lcdA is thereby involved in murein recycling. Is also essential for viability during stationary phase
Gene Name:
ldcA
Uniprot ID:
P76008
Molecular weight:
33567
Reactions
GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelyl-D-alanine + H(2)O = GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelate + D-alanine.
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppB
Uniprot ID:
P0AFH2
Molecular weight:
33443
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppC
Uniprot ID:
P0AFH6
Molecular weight:
33022
General function:
Involved in nucleotide binding
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides. Probably responsible for energy coupling to the transport system
Gene Name:
oppF
Uniprot ID:
P77737
Molecular weight:
37197
General function:
Involved in transporter activity
Specific function:
Essential for the uptake of the murein peptide L-alanyl- gamma-D-glutamyl-meso-diaminopimelate. Also transports some alpha- linked peptides such as Pro-Phe-Lys with low affinity. The transport is effected by the oligopeptide permease system
Gene Name:
mppA
Uniprot ID:
P77348
Molecular weight:
59900
General function:
Involved in metallocarboxypeptidase activity
Specific function:
Specific function unknown
Gene Name:
mpaA
Uniprot ID:
P0ACV6
Molecular weight:
26558
General function:
Involved in nucleotide binding
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides. Probably responsible for energy coupling to the transport system
Gene Name:
oppD
Uniprot ID:
P76027
Molecular weight:
37188
General function:
Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:
Involved in both cell wall peptidoglycans recycling and beta-lactamase induction. Specifically cleaves the amide bond between the lactyl group of N-acetylmuramic acid and the alpha- amino group of the L-alanine in degradation products containing an anhydro N-acetylmuramyl moiety
Gene Name:
ampD
Uniprot ID:
P13016
Molecular weight:
20536
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.
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
Uniprot ID:
P37773
Molecular weight:
49874

Transporters

General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppB
Uniprot ID:
P0AFH2
Molecular weight:
33443
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides; probably responsible for the translocation of the substrate across the membrane
Gene Name:
oppC
Uniprot ID:
P0AFH6
Molecular weight:
33022
General function:
Involved in nucleotide binding
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides. Probably responsible for energy coupling to the transport system
Gene Name:
oppF
Uniprot ID:
P77737
Molecular weight:
37197
General function:
Involved in transporter activity
Specific function:
Essential for the uptake of the murein peptide L-alanyl- gamma-D-glutamyl-meso-diaminopimelate. Also transports some alpha- linked peptides such as Pro-Phe-Lys with low affinity. The transport is effected by the oligopeptide permease system
Gene Name:
mppA
Uniprot ID:
P77348
Molecular weight:
59900
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in nucleotide binding
Specific function:
Part of the binding-protein-dependent transport system for oligopeptides. Probably responsible for energy coupling to the transport system
Gene Name:
oppD
Uniprot ID:
P76027
Molecular weight:
37188
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368