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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:03:21 UTC
Update Date2022-09-22 18:35:08 UTC
HMDB IDHMDB0029011
Secondary Accession Numbers
  • HMDB29011
Metabolite Identification
Common NameProlyl-Arginine
DescriptionProlyl-Arginine is a dipeptide composed of proline and arginine. 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
Data?1582753365
Synonyms
ValueSource
L-Prolyl-L-arginineHMDB
p-R DipeptideHMDB
PR DipeptideHMDB
Pro-argHMDB
Proline arginine dipeptideHMDB
Proline-arginine dipeptideHMDB
ProlylarginineHMDB
Prolylarginine, (D-arg-L-pro)-isomerHMDB
Prolylarginine, (L-arg-D-pro)-isomerHMDB
5-Carbamimidamido-2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}pentanoateHMDB
Chemical FormulaC11H21N5O3
Average Molecular Weight271.3161
Monoisotopic Molecular Weight271.164439563
IUPAC Name5-carbamimidamido-2-[(pyrrolidin-2-yl)formamido]pentanoic acid
Traditional Name5-carbamimidamido-2-(pyrrolidin-2-ylformamido)pentanoic acid
CAS Registry NumberNot Available
SMILES
NC(=N)NCCCC(NC(=O)C1CCCN1)C(O)=O
InChI Identifier
InChI=1S/C11H21N5O3/c12-11(13)15-6-2-4-8(10(18)19)16-9(17)7-3-1-5-14-7/h7-8,14H,1-6H2,(H,16,17)(H,18,19)(H4,12,13,15)
InChI KeyHMNSRTLZAJHSIK-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
  • Proline or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Heterocyclic fatty acid
  • Fatty acyl
  • Fatty acid
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Guanidine
  • Amino acid
  • Secondary carboxylic acid amide
  • Organoheterocyclic compound
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Secondary amine
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • 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-3.41Extrapolated
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112027
KNApSAcK IDNot Available
Chemspider ID7989825
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9814075
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. Schug KA, Lindner W, Lemr K: Isomeric discrimination of arginine-containing dipeptides using electrospray ionization-ion trap mass spectrometry and the kinetic method. J Am Soc Mass Spectrom. 2004 Jun;15(6):840-7. [PubMed:15144973 ]
  2. Kurzwelly D, Barann M, Kostanian A, Combrink S, Bonisch H, Gothert M, Bruss M: Pharmacological and electrophysiological properties of the naturally occurring Pro391Arg variant of the human 5-HT3A receptor. Pharmacogenetics. 2004 Mar;14(3):165-72. [PubMed:15167704 ]
  3. Zhu YS, Zhang XY, Cartwright CP, Tipper DJ: Kex2-dependent processing of yeast K1 killer preprotoxin includes cleavage at ProArg-44. Mol Microbiol. 1992 Feb;6(4):511-20. [PubMed:1560780 ]
  4. Yegneswaran S, Nguyen PM, Gale AJ, Griffin JH: Prothrombin amino terminal region helps protect coagulation factor Va from proteolytic inactivation by activated protein C. Thromb Haemost. 2009 Jan;101(1):55-61. [PubMed:19132189 ]
  5. Chang JY, Alkan SS, Hilschmann N, Braun DG: Thrombin specificity. Selective cleavage of antibody light chains at the joints of variable with joining regions and joining with constant regions. Eur J Biochem. 1985 Sep 2;151(2):225-30. [PubMed:3928376 ]