Record Information
Version2.0
Creation Date2012-07-30 14:55:05 -0600
Update Date2015-06-03 17:20:58 -0600
Secondary Accession Numbers
  • ECMDB21239
Identification
Name:L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine
Description:L-alanine-d-glutamate-meso-2,6-diaminoheptanedioate-d-alanine 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-glutamic acid-meso-2,6-diaminoheptanedioic acid-D-alanine
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
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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
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 Solubility0.179 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity107.89 m3·mol-1ChemAxon
Polarizability45.04 Å3ChemAxon
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 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
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 IDCPD0-2256
EcoCyc IDCPD0-2256

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:
This protein is a component of the oligopeptide permease, a binding protein-dependent transport system, it binds peptides up to five amino acids long with high affinity
Gene Name:
oppA
Uniprot ID:
P23843
Molecular weight:
60899
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:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
This protein is a component of the oligopeptide permease, a binding protein-dependent transport system, it binds peptides up to five amino acids long with high affinity
Gene Name:
oppA
Uniprot ID:
P23843
Molecular weight:
60899
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