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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:03:21 UTC
Update Date2022-09-22 18:34:23 UTC
HMDB IDHMDB0029010
Secondary Accession Numbers
  • HMDB29010
Metabolite Identification
Common NameProlyl-Alanine
DescriptionProlyl-Alanine is a dipeptide composed of proline and alanine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite.
Structure
Thumb
Synonyms
ValueSource
L-Prolyl-L-alanineHMDB
p-a DipeptideHMDB
PA dipeptideHMDB
Pro-alaHMDB
Proline alanine dipeptideHMDB
Proline-alanine dipeptideHMDB
ProlylalanineHMDB
2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}propanoateHMDB
Chemical FormulaC8H14N2O3
Average Molecular Weight186.2084
Monoisotopic Molecular Weight186.100442324
IUPAC Name2-[(pyrrolidin-2-yl)formamido]propanoic acid
Traditional Name2-(pyrrolidin-2-ylformamido)propanoic acid
CAS Registry NumberNot Available
SMILES
CC(NC(=O)C1CCCN1)C(O)=O
InChI Identifier
InChI=1S/C8H14N2O3/c1-5(8(12)13)10-7(11)6-3-2-4-9-6/h5-6,9H,2-4H2,1H3,(H,10,11)(H,12,13)
InChI KeyFELJDCNGZFDUNR-UHFFFAOYSA-N
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
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Proline or derivatives
  • Alpha-amino acid amide
  • Alanine or derivatives
  • Alpha-amino acid or derivatives
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Secondary aliphatic amine
  • Carboxylic acid
  • Azacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.11Extrapolated
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112026
KNApSAcK IDNot Available
Chemspider ID370069
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound418041
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pierpoint WS: o-Quinones formed in plant extracts. Their reactions with amino acids and peptides. Biochem J. 1969 May;112(5):609-16. [PubMed:4980678 ]
  2. Paynter RA, Hankinson SE, Colditz GA, Hunter DJ, De Vivo I: No evidence of a role for PPARgamma Pro12Ala polymorphism in endometrial cancer susceptibility. Pharmacogenetics. 2004 Dec;14(12):851-6. [PubMed:15608564 ]
  3. Unnithan AG, Myer MJ, Veale CJ, Danell AS: MS/MS of protonated polyproline peptides: the influence of N-terminal protonation on dissociation. J Am Soc Mass Spectrom. 2007 Dec;18(12):2198-203. Epub 2007 Oct 2. [PubMed:17964801 ]
  4. Patamia M, Messana I, Petruzzelli R, Vitali A, Inzitari R, Cabras T, Fanali C, Scarano E, Contucci A, Galtieri A, Castagnola M: Two proline-rich peptides from pig (Sus scrofa) salivary glands generated by pre-secretory pathway underlying the action of a proteinase cleaving ProAla bonds. Peptides. 2005 Sep;26(9):1550-9. Epub 2005 Apr 18. [PubMed:16112392 ]