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Arginyl-Proline

July 24, 2017
Common Name

Arginyl-Proline Description

Arginyl-Proline is a dipeptide composed of arginine and proline. 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

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source Arg-proHMDB Arginine proline dipeptideHMDB Arginine-proline dipeptideHMDB ArginylprolineHMDB L-Arginyl-L-prolineHMDB R-P DipeptideHMDB RP DipeptideHMDB Arginylproline diacetate, (L)-isomerMeSH

Chemical Formlia

C11H21N5O3 Average Molecliar Weight

271.3161 Monoisotopic Molecliar Weight

271.164439563 IUPAC Name

1-(2-amino-5-carbamimidamidopentanoyl)pyrrolidine-2-carboxylic acid Traditional Name

1-(2-amino-5-carbamimidamidopentanoyl)pyrrolidine-2-carboxylic acid CAS Registry Number

Not Available SMILES

NC(CCCNC(N)=N)C(=O)N1CCCC1C(O)=O

InChI Identifier

InChI=1S/C11H21N5O3/c12-7(3-1-5-15-11(13)14)9(17)16-6-2-4-8(16)10(18)19/h7-8H,1-6,12H2,(H,18,19)(H4,13,14,15)

InChI Key

LQJAALCCPOTJGB-UHFFFAOYSA-N Chemical Taxonomy Description

This 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. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

Dipeptides Alternative Parents

  • Proline and derivatives
  • N-acyl-alpha amino acids
  • Alpha amino acid amides
  • Pyrrolidine carboxylic acids
  • N-acylpyrrolidines
  • Tertiary carboxylic acid amides
  • Amino acids
  • Guanidines
  • Propargyl-type 1,3-dipolar organic compounds
  • Azacyclic compounds
  • Carboximidamides
  • Carboxylic acids
  • Monocarboxylic acids and derivatives
  • Carbonyl compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Monoalkylamines
  • Organopnictogen compounds

    • Substituents

  • Alpha-dipeptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Proline or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Guanidine
  • Amino acid
  • Azacycle
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Aliphatic heteromonocyclic compound

    • Molecliar Framework

    Aliphatic heteromonocyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Endogenous

    • Biofunction

    Not Available Application

    Not Available Cellliar locations

    Not Available Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogP-3.25Extrapolated

    Predicted Properties

    Property Value Source Water Solubility1.09 mg/mLALOGPS logP-3.5ALOGPS logP-3.4ChemAxon logS-2.4ALOGPS pKa (Strongest Acidic)3.65ChemAxon pKa (Strongest Basic)12.02ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count7ChemAxon Hydrogen Donor Count5ChemAxon Polar Surface Area145.53 Å2ChemAxon Rotatable Bond Count6ChemAxon Refractivity78.91 m3·mol-1ChemAxon Polarizability28.18 Å3ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

    Not Available Biofluid Locations

    Not Available Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations Not Available Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    Not Available KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB28717 Metagene Link

    HMDB28717 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: Quinapril (hydrochloride)

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Bisof V, Salihovic MP, Narancic NS, Skaric-Juric T, Jakic-Razumovic J, Janicijevic B, Turek S, Rudan P: TP53 gene polymorphisms and breast cancer in Croatian women: a pilot study. Eur J Gynaecol Oncol. 2010;31(5):539-44. [PubMed:21061796 ]
    2. Nadji SA, Mahmoodi M, Ziaee AA, Naghshvar F, Torabizadeh J, Yahyapour Y, Nategh R, Mokhtari-Azad T: An increased lung cancer risk associated with codon 72 polymorphism in the TP53 gene and human papillomavirus infection in Mazandaran province, Iran. Lung Cancer. 2007 May;56(2):145-51. Epub 2007 Jan 8. [PubMed:17208332 ]
    3. Hamajima N, Matsuo K, Suzuki T, Nakamura T, Matsuura A, Hatooka S, Shinoda M, Kodera Y, Yamamura Y, Hirai T, Kato T, Tajima K: No associations of p73 G4C14-to-A4T14 at exon 2 and p53 Arg72Pro polymorphisms with the risk of digestive tract cancers in Japanese. Cancer Lett. 2002 Jul 8;181(1):81-5. [PubMed:12430182 ]
    4. Havranek O, Spacek M, Hubacek P, Mocikova H, Benesova K, Soucek P, Trneny M, Kleibl Z: No association between the TP53 codon 72 polymorphism and risk or prognosis of Hodgkin and non-Hodgkin lymphoma. Leuk Res. 2011 Aug;35(8):1117-9. doi: 10.1016/j.leukres.2011.04.001. Epub 2011 May 5. [PubMed:21546086 ]
    5. Lacha J, Hubacek JA, Potmesil P, Viklicky O, Malek I, Vitko S: TGF-beta I gene polymorphism in heart transplant recipients–effect on renal function. Ann Transplant. 2001;6(1):39-43. [PubMed:11803605 ]
    6. Mitchell WM: Hydrolysis at arginylproline in polypeptides by clostridiopeptidase B. Science. 1968 Oct 18;162(3851):374-5. [PubMed:5677534 ]
    7. Irarrazabal CE, Rojas C, Aracena R, Marquez C, Gil L: Chilean pilot study on the risk of lung cancer associated with codon 72 polymorphism in the gene of protein p53. Toxicol Lett. 2003 Sep 15;144(1):69-76. [PubMed:12919725 ]
    8. 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 ]

    PMID: 16221703

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