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Glycyl-Serine

July 21, 2017
Common Name

Glycyl-Serine Description

Glycyl-Serine is a dipeptide composed of glycine 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 HMDB28850 (Glycyl-Serine)

Synonyms

Value Source g-S DipeptideHMDB Gly-serHMDB Glycine serine dipeptideHMDB Glycine-serine dipeptideHMDB GlycylserineHMDB GS DipeptideHMDB L-Glycyl-L-serineHMDB

Chemical Formlia

C5H10N2O4 Average Molecliar Weight

162.1439 Monoisotopic Molecliar Weight

162.064056818 IUPAC Name

2-(2-aminoacetamido)-3-hydroxypropanoic acid Traditional Name

2-(2-aminoacetamido)-3-hydroxypropanoic acid CAS Registry Number

Not Available SMILES

NCC(=O)NC(CO)C(O)=O

InChI Identifier

InChI=1S/C5H10N2O4/c6-1-4(9)7-3(2-8)5(10)11/h3,8H,1-2,6H2,(H,7,9)(H,10,11)

InChI Key

BCCRXDTUTZHDEU-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

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

    • Substituents

  • Alpha-dipeptide
  • 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
  • Hydroxy acid
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Alcohol
  • Amine
  • Organooxygen compound
  • Primary alcohol
  • Primary amine
  • Organic oxygen compound
  • Aliphatic acyclic compound

    • Molecliar Framework

    Aliphatic acyclic compounds External Descriptors

    Not Available Ontology Status

    Detected 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-5.0Extrapolated

    Predicted Properties

    Property Value Source Water Solubility90.4 mg/mLALOGPS logP-3.3ALOGPS logP-5ChemAxon logS-0.25ALOGPS pKa (Strongest Acidic)3.36ChemAxon pKa (Strongest Basic)8.14ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area112.65 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity34.84 m3·mol-1ChemAxon Polarizability14.76 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

  • Sweat

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations Not Available Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details SweatDetected but not Quantified Infant (0-1 year old)Not Specifiedscreen-positive CF

  • Adriana Nori…

    • details

    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

    HMDB28850 Metagene Link

    HMDB28850 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: Nicotinamide N-oxide

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Blagojevic V, Chramow A, Schneider BB, Covey TR, Bohme DK: Differential mobility spectrometry of isomeric protonated dipeptides: modifier and field effects on ion mobility and stability. Anal Chem. 2011 May 1;83(9):3470-6. doi: 10.1021/ac200100s. Epub 2011 Apr 19. [PubMed:21504141 ]
    2. Benz R, Francis G, Nakae T, Ferenci T: Investigation of the selectivity of maltoporin channels using mutant LamB proteins: mutations changing the maltodextrin binding site. Biochim Biophys Acta. 1992 Mar 2;1104(2):299-307. [PubMed:1547266 ]
    3. Robinson JM, Hardman JK, Sloan GL: Relationship between lysostaphin endopeptidase production and cell wall composition in Staphylococcus staphylolyticus. J Bacteriol. 1979 Mar;137(3):1158-64. [PubMed:438117 ]
    4. Fujii Y, Kiss T, Gajda T, Tan XS, Sato T, Nakano Y, Hayashi Y, Yashiro M: Copper(II)- cis, cis-1,3,5-triaminocyclohexane complex-promoted hydrolysis of dipeptides: kinetic, speciation and structural studies. J Biol Inorg Chem. 2002 Sep;7(7-8):843-51. Epub 2002 Apr 30. [PubMed:12203021 ]
    5. Weber AL, Orgel LE: The formation of peptides from the 2(3)-glycyl ester of a nucleotide. J Mol Evol. 1978 Aug 2;11(3):189-98. [PubMed:29132 ]
    6. Weber AL, Orgel LE: The formation of dipeptides from amino acids and the 2(3)-glycyl ester of an adenylate. J Mol Evol. 1979 Oct;13(3):185-92. [PubMed:501742 ]
    7. Kucukhuseyin O, Yilmaz-Aydogan H, Isbir CS, Isbir T: Is there any association between GLY82 ser polymorphism of rage gene and Turkish diabetic and non diabetic patients with coronary artery disease? Mol Biol Rep. 2012 Apr;39(4):4423-8. doi: 10.1007/s11033-011-1230-3. Epub 2011 Sep 25. [PubMed:21947881 ]
    8. Wang DX, Lu GS, Liu W, Wang NG, Guan MZ, Zhao YL, Wang XN, Cheng ZP: [Synthesis of small peptides containing hydroxy-amino-acid, and its effects on progesterone production]. Yao Xue Xue Bao. 1991;26(1):25-9. [PubMed:1887790 ]
    9. 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 ]
    10. Olafsen T, Tan GJ, Cheung CW, Yazaki PJ, Park JM, Shively JE, Williams LE, Raubitschek AA, Press MF, Wu AM: Characterization of engineered anti-p185HER-2 (scFv-CH3)2 antibody fragments (minibodies) for tumor targeting. Protein Eng Des Sel. 2004 Apr;17(4):315-23. Epub 2004 Jun 8. [PubMed:15187222 ]
    11. Shiomi K, Yang H, Inokoshi J, Van der Pyl D, Nakagawa A, Takeshima H, Omura S: Pepticinnamins, new farnesyl-protein transferase inhibitors produced by an actinomycete. II. Structural elucidation of pepticinnamin E. J Antibiot (Tokyo). 1993 Feb;46(2):229-34. [PubMed:8468236 ]
    12. Buhl M: Density-functional study of vanadate-glycylserine isomers. J Inorg Biochem. 2000 May 30;80(1-2):137-9. [PubMed:10885474 ]
    13. Toyoda T, Sakaguchi T, Imai K, Inocencio NM, Gotoh B, Hamaguchi M, Nagai Y: Structural comparison of the cleavage-activation site of the fusion glycoprotein between virulent and avirulent strains of Newcastle disease virus. Virology. 1987 May;158(1):242-7. [PubMed:3576973 ]
    14. 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 ]
    15. Sahoo H, Roccatano D, Zacharias M, Nau WM: Distance distributions of short polypeptides recovered by fluorescence resonance energy transfer in the 10 A domain. J Am Chem Soc. 2006 Jun 28;128(25):8118-9. [PubMed:16787059 ]

    PMID: 8804051

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