Sat. Sep 7th, 2024

N-Acetyl-L-alanine

By rofalproject
Common Name

N-Acetyl-L-alanine Description

N-Acetyl-L-alanine is a substrate for Guanine nucleotide-binding protein G(I)/G(S)/G(O) gamma-2 subunit, Myelin basic protein, GTP-binding nuclear protein Ran, Tropomyosin alpha 4 chain, HIV-1 Rev binding protein 2, Xaa-Pro dipeptidase, Thymosin beta-10, Actin-like protein 3, Alanine aminotransferase, Serine/threonine protein phosphatase PP1-beta catalytic subunit, 10 kDa heat shock protein (mitochondrial), Calmodliin and Beta-1-syntrophin. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (S)-2-(acetylamino)Propanoic acidChEBI 2-Acetamidopropionic acidChEBI Ac-ala-OHChEBI AcetylalanineChEBI L-N-AcetylalanineChEBI N-Acetyl-L-alpha-alanineChEBI N-Acetyl-S-alanineChEBI N-AcetylalanineChEBI (S)-2-(acetylamino)PropanoateGenerator 2-AcetamidopropionateGenerator N-Acetyl-L-a-alanineGenerator N-Acetyl-L-α-alanineGenerator (S)-(-)-N-AcetylalanineHMDB (S)-N-AcetylalanineHMDB Acetyl-L-alanineHMDB N-Acetyl-(S)-alanineHMDB

Chemical Formlia

C5H9NO3 Average Molecliar Weight

131.1299 Monoisotopic Molecliar Weight

131.058243159 IUPAC Name

(2S)-2-acetamidopropanoic acid Traditional Name

N-acetylalanine CAS Registry Number

97-69-8 SMILES

C[C@H](NC(C)=O)C(O)=O

InChI Identifier

InChI=1S/C5H9NO3/c1-3(5(8)9)6-4(2)7/h3H,1-2H3,(H,6,7)(H,8,9)/t3-/m0/s1

InChI Key

KTHDTJVBEPMMGL-VKHMYHEASA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

N-acyl-L-alpha-amino acids Alternative Parents

  • Alanine and derivatives
  • Acetamides
  • Secondary carboxylic acid amides
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Organopnictogen compounds
  • Organonitrogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • N-acyl-l-alpha-amino acid
  • Alanine or derivatives
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound

    • Molecliar Framework

    Aliphatic acyclic compounds External Descriptors

  • L-alanine derivative (CHEBI:40992 )
  • N-acetyl-L-amino acid (CHEBI:40992 )

    • Ontology Status

    Detected and Quantified Origin

  • Endogenous

    • Biofunction

  • Protein synthesis, amino acid biosynthesis

    • Application

    Not Available Cellliar locations

  • Cytoplasm (predicted from logP)

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility43.6 mg/mLALOGPS logP-0.53ALOGPS logP-0.76ChemAxon logS-0.48ALOGPS pKa (Strongest Acidic)3.89ChemAxon pKa (Strongest Basic)-1.5ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area66.4 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity29.94 m3·mol-1ChemAxon Polarizability12.49 Å3ChemAxon Number of Rings0ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key GC-MS

    GC-MS Spectrum – GC-MS (1 TMS)splash10-05n0-2900000000-c0a5e66723f41ac78751View in MoNA Predicted GC-MS

    Predicted GC-MS Spectrum – GC-MSNot Available LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9000000000-4cea4517104b7a324debView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-4497242e6b422cf3f913View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-22d764f7b773b82c6515View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , negativesplash10-000i-9000000000-e6becb5f8b8bbb53304aView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available 1D NMR

    13C NMR SpectrumNot Available 1D NMR

    1H NMR SpectrumNot Available 2D NMR

    [1H,1H] 2D NMR SpectrumNot Available 2D NMR

    [1H,13C] 2D NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm (predicted from logP)

    • Biofluid Locations

  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations Not Available Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details UrineDetected and Quantified0.5 (0.0-1.0) umol/mmol creatinineAdlit (>18 years old)Both

    Prostate Cancer

  • 19212411

    • details

    Associated Disorders and Diseases Disease References

    Prostate cancer

    1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]

    Associated OMIM IDs

  • 176807 (Prostate cancer)

    • 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

    FDB022231 KNApSAcK ID

    Not Available Chemspider ID

    79449 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB00766 Metagene Link

    HMDB00766 METLIN ID

    5733 PubChem Compound

    88064 PDB ID

    AYA ChEBI ID

    40992

    Product: Tyrphostin AG 879

    References Synthesis Reference Vanzura, Jiri; Kasafirek, Evzen; Hrabalek, Alexandr; Vinsova, Jarmila; Krepelka, Jiri. Process for preparing highly pure N-acetyl-L- or -D-alanine. Czech. (1989), 4 pp. Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in catalytic activity
    Specific function:
    Involved in the urea cycle of ureotelic animals where the enzyme plays an important role in removing excess ammonia from the cell.
    Gene Name:
    CPS1
    Uniprot ID:
    P31327
    Molecular weight:
    165649.075
    General function:
    Involved in N-acetyltransferase activity
    Specific function:
    Plays a role in the regulation of ureagenesis by producing variable amounts of N-acetylglutamate (NAG), thus modulating carbamoylphosphate synthase I (CPSI) activity.
    Gene Name:
    NAGS
    Uniprot ID:
    Q8N159
    Molecular weight:
    58155.835
    General function:
    Involved in glycine N-acyltransferase activity
    Specific function:
    Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
    Gene Name:
    GLYAT
    Uniprot ID:
    Q6IB77
    Molecular weight:
    18506.33
    General function:
    Involved in glycine N-acyltransferase activity
    Specific function:
    Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
    Gene Name:
    GLYATL1
    Uniprot ID:
    Q969I3
    Molecular weight:
    35100.895
    General function:
    Involved in glycine N-acyltransferase activity
    Specific function:
    Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
    Gene Name:
    GLYATL2
    Uniprot ID:
    Q8WU03
    Molecular weight:
    34277.055

    PMID: 19299917

    By rofalproject

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