L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine (PAMDB001647)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001647
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
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🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • L-Alanine-D-glutamic acid-meso-2,6-diaminoheptanedioic acid-D-alanine
Chemical Formula: C18H31N5O9
Average Molecular Weight: 461.4668
Monoisotopic Molecular Weight: 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
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
  • Alpha-amino acid or derivatives
  • Tricarboxylic acid or derivatives
  • 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: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:
Adenosine triphosphate + Water + L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine > L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + ADP + Hydrogen ion + Phosphate
Adenosine triphosphate + Water + L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine > L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + ADP + Hydrogen ion + Phosphate
N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide + Water > L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramic acid
1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide + Water > L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + 1,6-Anhydro-N-acetylmuramate
L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + Water > L-alanine-D-glutamate-meso-2,6-diaminoheptanedioate + D-Alanine
Pathways: 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

Protein Details
• N-acetylmuramoyl-L-alanine amidase AmiB
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
Locus Tag:
PA4947
Molecular weight:
50.7 kDa
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.
Protein Details
• Probable N-acetylmuramoyl-L-alanine amidase AmiA
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
Locus Tag:
PA5538
Molecular weight:
42.9 kDa
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.
Protein Details
• N-acetylmuramoyl-L-alanine amidase AmiC
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
Locus Tag:
PA3364
Molecular weight:
42.8 kDa
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.
Protein Details
• Murein tetrapeptide carboxypeptidase
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
Locus Tag:
PA1818
Molecular weight:
82.8 kDa
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.
Protein Details
• 1,6-anhydro-N-acetylmuramyl-L-alanine amidase AmpD
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
Locus Tag:
PA4522
Molecular weight:
21 kDa
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.
Protein Details
• UDP-N-acetylmuramate:L-alanyl-gamma-D-glutamyl-meso-diaminopimelate ligase
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