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Leucyl-Serine

July 21, 2017
Common Name

Leucyl-Serine Description

Leucyl-Serine is a dipeptide composed of leucine and serine. 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

Structure for HMDB28938 (Leucyl-Serine)

Synonyms

Value Source L-Leucyl-L-serineHMDB L-S DipeptideHMDB Leu-serHMDB Leucine serine dipeptideHMDB Leucine-serine dipeptideHMDB LeucylserineHMDB LS DipeptideHMDB

Chemical Formlia

C9H18N2O4 Average Molecliar Weight

218.2502 Monoisotopic Molecliar Weight

218.126657074 IUPAC Name

2-(2-amino-4-methylpentanamido)-3-hydroxypropanoic acid Traditional Name

2-(2-amino-4-methylpentanamido)-3-hydroxypropanoic acid CAS Registry Number

Not Available SMILES

CC(C)CC(N)C(=O)NC(CO)C(O)=O

InChI Identifier

InChI=1S/C9H18N2O4/c1-5(2)3-6(10)8(13)11-7(4-12)9(14)15/h5-7,12H,3-4,10H2,1-2H3,(H,11,13)(H,14,15)

InChI Key

XGDCYUQSFDQISZ-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
  • Serine and derivatives
  • Alpha amino acid amides
  • Beta hydroxy acids and derivatives
  • N-acyl amines
  • Secondary carboxylic acid amides
  • Amino acids
  • Carboxylic acids
  • Monocarboxylic acids and derivatives
  • Hydrocarbon derivatives
  • Primary alcohols
  • Carbonyl compounds
  • Organic oxides
  • Organopnictogen compounds
  • Monoalkylamines

    • Substituents

  • Alpha-dipeptide
  • Leucine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Serine or derivatives
  • Alpha-amino acid or derivatives
  • Beta-hydroxy acid
  • Fatty amide
  • Hydroxy acid
  • N-acyl-amine
  • Fatty acyl
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Alcohol
  • Amine
  • Primary amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • 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-3.17Extrapolated

    Predicted Properties

    Property Value Source Water Solubility51.2 mg/mLALOGPS logP-2.5ALOGPS logP-3.2ChemAxon logS-0.63ALOGPS pKa (Strongest Acidic)3.74ChemAxon pKa (Strongest Basic)8.43ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area112.65 Å2ChemAxon Rotatable Bond Count6ChemAxon Refractivity53.01 m3·mol-1ChemAxon Polarizability22.69 Å3ChemAxon 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

    HMDB28938 Metagene Link

    HMDB28938 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: BIA 10-2474

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Ho PH, Stroobants K, Parac-Vogt TN: Hydrolysis of serine-containing peptides at neutral pH promoted by [MoO4]2- oxyanion. Inorg Chem. 2011 Dec 5;50(23):12025-33. doi: 10.1021/ic2015034. Epub 2011 Oct 31. [PubMed:22040112 ]
    2. Ho PH, Mihaylov T, Pierloot K, Parac-Vogt TN: Hydrolytic activity of vanadate toward serine-containing peptides studied by kinetic experiments and DFT theory. Inorg Chem. 2012 Aug 20;51(16):8848-59. doi: 10.1021/ic300761g. Epub 2012 Jul 30. [PubMed:22845736 ]
    3. Wibisono HT, Linkie M, Guillera-Arroita G, Smith JA, Sunarto, Pusparini W, Asriadi, Baroto P, Brickle N, Dinata Y, Gemita E, Gunaryadi D, Haidir IA, Herwansyah, Karina I, Kiswayadi D, Kristiantono D, Kurniawan H, Lahoz-Monfort JJ, Leader-Williams N, Maddox T, Martyr DJ, Maryati, Nugroho A, Parakkasi K, Priatna D, Ramadiyanta E, Ramono WS, Reddy GV, Rood EJ, Saputra DY, Sarimudi A, Salampessy A, Septayuda E, Suhartono T, Sumantri A, Susilo, Tanjung I, Tarmizi, Yulianto K, Yunus M, Zulfahmi: Population status of a cryptic top predator: an island-wide assessment of tigers in Sumatran rainforests. PLoS One. 2011;6(11):e25931. doi: 10.1371/journal.pone.0025931. Epub 2011 Nov 2. [PubMed:22087218 ]
    4. Girard-Buttoz C, Heistermann M, Krummel S, Engelhardt A: Seasonal and social influences on fecal androgen and glucocorticoid excretion in wild male long-tailed macaques (Macaca fascicularis). Physiol Behav. 2009 Aug 4;98(1-2):168-75. doi: 10.1016/j.physbeh.2009.05.005. Epub 2009 May 18. [PubMed:19454293 ]
    5. Sugardjito J, van Hooff JA: Age-sex class differences in the positional behaviour of the Sumatran orang-utan (Pongo pygmaeus abelii) in the Gunung Leuser National Park, Indonesia. Folia Primatol (Basel). 1986;47(1):14-25. [PubMed:3557227 ]
    6. Elliott S, Brimacombe J: The medicinal plants of Gunung Leuser National Park, Indonesia. J Ethnopharmacol. 1987 May;19(3):285-317. [PubMed:3669690 ]
    7. Ungar PS: Patterns of ingestive behavior and anterior tooth use differences in sympatric anthropoid primates. Am J Phys Anthropol. 1994 Oct;95(2):197-219. [PubMed:7802096 ]
    8. McWherter CA, Rocque WJ, Zupec ME, Freeman SK, Brown DL, Devadas B, Getman DP, Sikorski JA, Gordon JI: Scanning alanine mutagenesis and de-peptidization of a Candida albicans myristoyl-CoA:protein N-myristoyltransferase octapeptide substrate reveals three elements critical for molecular recognition. J Biol Chem. 1997 May 2;272(18):11874-80. [PubMed:9115247 ]
    9. Thorpe SK, Crompton RH: Locomotor ecology of wild orangutans (Pongo pygmaeus abelii) in the Gunung Leuser Ecosystem, Sumatra, Indonesia: a multivariate analysis using log-linear modelling. Am J Phys Anthropol. 2005 May;127(1):58-78. [PubMed:15386279 ]
    10. Wich S, Buij R, van Schaik C: Determinants of orangutan density in the dryland forests of the Leuser Ecosystem. Primates. 2004 Jul;45(3):177-82. Epub 2004 Apr 20. [PubMed:15098098 ]

    PMID: 1982626

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