Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001645
Identification
Name: L-Prolinylglycine
Description:Prolinylglycine is a dipeptide. It is a proteolytic breakdown product of larger proteins. Pseudomonas aeruginosa can use this dipeptide as a substrate for carbon/nitrogen metabolism and a source of proline. It is transported via DppA, which appears to be both a dipeptide transporter and a dipeptidase. Pro-Gly utilization does not require any of the three major proline transport systems. [PMID:1702779]
Structure
Thumb
Synonyms:
  • ((2-pyrrolidinylcarbonyl)amino)acetate
  • ((2-pyrrolidinylcarbonyl)amino)acetic acid
  • L-Prolinylglycine
  • L-Prolylglycine
  • L-Prolylgycine
  • N-L-Prolyl-Glycine
  • Pro-Gly
  • Prolylglycine
Chemical Formula: C7H12N2O3
Average Molecular Weight: 172.1818
Monoisotopic Molecular Weight: 172.08479226
InChI Key: RNKSNIBMTUYWSH-UHFFFAOYSA-N
InChI:InChI=1S/C7H12N2O3/c10-6(11)4-9-7(12)5-2-1-3-8-5/h5,8H,1-4H2,(H,9,12)(H,10,11)
CAS number: 2578-57-6
IUPAC Name:2-(pyrrolidin-2-ylformamido)acetic acid
Traditional IUPAC Name: (pyrrolidin-2-ylformamido)acetic acid
SMILES:OC(=O)CNC(=O)C1CCCN1
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 amide
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Pyrrolidine-2-carboxamide
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Secondary aliphatic amine
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility6.91 mg/mLALOGPS
logP-2.9ALOGPS
logP-3.7ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.66ChemAxon
pKa (Strongest Basic)9.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area78.43 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity40.87 m3·mol-1ChemAxon
Polarizability17.07 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-00di-6900000000-057d72c7813e86a7fd98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9100000000-05a4b0dbdd1dc09295e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9000000000-36b9e0d3dbb8b2f9ae2fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1900000000-0034ef8a997bcb9ff06aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-8900000000-128eb62510d75852e054View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9000000000-da6e1d91757d26d9b0b2View in MoNA
References
References:
  • Jandke J, Spiteller G: Dipeptide analysis in human urine. J Chromatogr. 1986 Oct 31;382:39-45. Pubmed: 3782411
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID61695
HMDB IDHMDB11178
Pubchem Compound ID98206
Kegg IDNot Available
ChemSpider ID88677
Wikipedia IDNot Available
BioCyc IDCPD0-2182
EcoCyc IDCPD0-2182

Enzymes

General function:
Involved in proteolysis
Specific function:
Aminopeptidase N is involved in the degradation of intracellular peptides generated by protein breakdown during normal growth as well as in response to nutrient starvation
Gene Name:
pepN
Locus Tag:
PA3083
Molecular weight:
100 kDa
Reactions
Release of an N-terminal amino acid, Xaa-|-Yaa- from a peptide, amide or arylamide. Xaa is preferably Ala, but may be most amino acids including Pro (slow action). When a terminal hydrophobic residue is followed by a prolyl residue, the two may be released as an intact Xaa-Pro dipeptide.
General function:
Involved in aminopeptidase activity
Specific function:
Presumably involved in the processing and regular turnover of intracellular proteins. Catalyzes the removal of unsubstituted N-terminal amino acids from various peptides. Required for plasmid ColE1 site-specific recombination but not in its aminopeptidase activity. Could act as a structural component of the putative nucleoprotein complex in which the Xer recombination reaction takes place
Gene Name:
pepA
Locus Tag:
PA3831
Molecular weight:
52.3 kDa
Reactions
Release of an N-terminal amino acid, Xaa-|-Yaa-, in which Xaa is preferably Leu, but may be other amino acids including Pro although not Arg or Lys, and Yaa may be Pro. Amino acid amides and methyl esters are also readily hydrolyzed, but rates on arylamides are exceedingly low.
Release of an N-terminal amino acid, preferentially leucine, but not glutamic or aspartic acids.
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 nucleotide binding
Specific function:
Part of the binding-protein-dependent transport system for dipeptides. Probably responsible for energy coupling to the transport system
Gene Name:
dppD
Locus Tag:
PA4505
Molecular weight:
35.4 kDa
General function:
Involved in nucleotide binding
Specific function:
Part of the binding-protein-dependent transport system for dipeptides. Probably responsible for energy coupling to the transport system
Gene Name:
dppF
Locus Tag:
PA4506
Molecular weight:
36.3 kDa
General function:
Involved in transporter activity
Specific function:
Dipeptide-binding protein of a transport system that can be subject to osmotic shock. DppA is also required for peptide chemotaxis
Gene Name:
dppA
Locus Tag:
PA4496
Molecular weight:
60.1 kDa

Transporters

General function:
Involved in proteolysis
Specific function:
Aminopeptidase N is involved in the degradation of intracellular peptides generated by protein breakdown during normal growth as well as in response to nutrient starvation
Gene Name:
pepN
Locus Tag:
PA3083
Molecular weight:
100 kDa
Reactions
Release of an N-terminal amino acid, Xaa-|-Yaa- from a peptide, amide or arylamide. Xaa is preferably Ala, but may be most amino acids including Pro (slow action). When a terminal hydrophobic residue is followed by a prolyl residue, the two may be released as an intact Xaa-Pro dipeptide.
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 nucleotide binding
Specific function:
Part of the binding-protein-dependent transport system for dipeptides. Probably responsible for energy coupling to the transport system
Gene Name:
dppD
Locus Tag:
PA4505
Molecular weight:
35.4 kDa
General function:
Involved in nucleotide binding
Specific function:
Part of the binding-protein-dependent transport system for dipeptides. Probably responsible for energy coupling to the transport system
Gene Name:
dppF
Locus Tag:
PA4506
Molecular weight:
36.3 kDa
General function:
Involved in transporter activity
Specific function:
Dipeptide-binding protein of a transport system that can be subject to osmotic shock. DppA is also required for peptide chemotaxis
Gene Name:
dppA
Locus Tag:
PA4496
Molecular weight:
60.1 kDa