Leucyl-Alanine

Common Name

Leucyl-Alanine Description

Leucyl-Alanine is a dipeptide composed of leucine 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

Synonyms

Value Source L-a DipeptideHMDB L-Leucyl-L-alanineHMDB LA dipeptideHMDB Leu-alaHMDB Leucine alanine dipeptideHMDB Leucine-alanine dipeptideHMDB LeucylalanineHMDB

Chemical Formlia

C₉H₁₈N₂O₃ Average Molecliar Weight

202.2508 Monoisotopic Molecliar Weight

202.131742452 IUPAC Name

2-(2-amino-4-methylpentanamido)propanoic acid Traditional Name

leu-ala CAS Registry Number

Not Available SMILES

InChI Identifier

InChI Key

HSQGMTRYSIHDAC-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

Leucine and derivatives

N-acyl-alpha amino acids

Alpha amino acid amides

Alanine and derivatives

N-acyl amines

Secondary carboxylic acid amides

Amino acids

Monocarboxylic acids and derivatives

Carboxylic acids

Organopnictogen compounds

Organic oxides

Monoalkylamines

Hydrocarbon derivatives

Carbonyl compounds

Substituents

Alpha-dipeptide

Leucine or derivatives

N-acyl-alpha-amino acid

N-acyl-alpha amino acid or derivatives

Alpha-amino acid amide

Alanine or derivatives

Alpha-amino acid or derivatives

Fatty amide

Fatty acyl

N-acyl-amine

Amino acid or derivatives

Carboxamide group

Amino acid

Secondary carboxylic acid amide

Carboxylic acid

Monocarboxylic acid or derivatives

Primary amine

Organic nitrogen compound

Primary aliphatic amine

Hydrocarbon derivative

Organic oxide

Carbonyl group

Organopnictogen compound

Amine

Organic oxygen compound

Organooxygen compound

Organonitrogen compound

Aliphatic acyclic compound

Molecliar Framework

Aliphatic acyclic 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-2.13Extrapolated

Predicted Properties

Property Value Source Water Solubility20.6 mg/mLALOGPS logP-1.4ALOGPS logP-2.1ChemAxon logS-0.99ALOGPS pKa (Strongest Acidic)3.96ChemAxon pKa (Strongest Basic)8.43ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area92.42 ŲChemAxon Rotatable Bond Count5ChemAxon Refractivity51.47 m³·mol^-1ChemAxon Polarizability21.74 ųChemAxon Number of Rings0ChemAxon 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

HMDB28922 Metagene Link

HMDB28922 METLIN ID

Not Available PubChem Compound

Not Available PDB ID

Not Available ChEBI ID

Not Available

Product: Isosilybin

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References

1. Hong L, Turner RT 3rd, Koelsch G, Shin D, Ghosh AK, Tang J: Crystal structure of memapsin 2 (beta-secretase) in complex with an inhibitor OM00-3. Biochemistry. 2002 Sep 10;41(36):10963-7. [PubMed:12206667 ]
2. Nath M, Pokharia S, Eng G, Song X, Kumar A: New triorganotin (IV) derivatives of dipeptides as models for metal-protein interactions: synthesis, structural characterization and biological studies. Spectrochim Acta A Mol Biomol Spectrosc. 2006 Jan;63(1):66-75. Epub 2005 Jun 9. [PubMed:15950528 ]
3. Wang T, Simbulan-Rosenthal CM, Smulson ME, Chock PB, Yang DC: Polyubiquitylation of PARP-1 through ubiquitin K48 is modulated by activated DNA, NAD+, and dipeptides. J Cell Biochem. 2008 May 1;104(1):318-28. [PubMed:18041763 ]
4. Kilic N, Kustimur S, Arslan S, Aldemir H: Fluorometric determination of acid proteinase activity in vulvovaginal candidosis. Mycoses. 1996 Sep-Oct;39(9-10):347-51. [PubMed:9009656 ]
5. Krishnakumar SS, London E: Effect of sequence hydrophobicity and bilayer width upon the minimum length required for the formation of transmembrane helices in membranes. J Mol Biol. 2007 Nov 30;374(3):671-87. Epub 2007 Sep 20. [PubMed:17950311 ]
6. Bedner M, MacCrehan WA, Helz GR: Making chlorine greener: investigation of alternatives to sulfite for dechlorination. Water Res. 2004 May;38(10):2505-14. [PubMed:15159154 ]
7. Turner RT 3rd, Koelsch G, Hong L, Castanheira P, Ermolieff J, Ghosh AK, Tang J: Subsite specificity of memapsin 2 (beta-secretase): implications for inhibitor design. Biochemistry. 2001 Aug 28;40(34):10001-6. [PubMed:11513577 ]

PMID: 19056862