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N-Acetyl-L-methionine (M2MDB003432)

Record Information
Version2.0
Creation Date2012-10-10 12:13:48 -0600
Update Date2015-09-13 12:56:17 -0600
Secondary Accession Numbers
  • ECMDB23042
Identification
Name:N-Acetyl-L-methionine
DescriptionN-Acetyl-L-methionine is an acylated methionine derivative. The N-terminal methionine is often released from peptides and proteins in E. coli via methionine aminopeptidase. The free methionine can be acetylated by the enzyme YncA or N acyltransferase in a reaction using a CoA thioester as cofactor.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2S)-2-acetamido-4-Methylsulfanylbutanoate
  • (2S)-2-acetamido-4-methylsulfanylbutanoic acid
  • (2S)-2-acetamido-4-Methylsulphanylbutanoate
  • (2S)-2-acetamido-4-Methylsulphanylbutanoic acid
  • Acetyl-l-methionine
  • Acetylmethionin
  • Acetylmethionine
  • DL-n-acetylmethionine
  • L-(n-acetyl)methionine
  • L-n-acetyl-Methionine
  • Methionamine
  • Methionin
  • N-acetyl(methyl)homocysteine
  • N-acetyl-Methionine
  • N-acetyl-S-methylhomocysteine
  • N-acetylmethionine
  • Thiomedon
Chemical Formula:C7H13NO3S
Weight:Average: 191.248
Monoisotopic: 191.061613977
InChI Key:XUYPXLNMDZIRQH-LURJTMIESA-N
InChI:InChI=1S/C7H13NO3S/c1-5(9)8-6(7(10)11)3-4-12-2/h6H,3-4H2,1-2H3,(H,8,9)(H,10,11)/t6-/m0/s1
CAS number:65-82-7
IUPAC Name:2-acetamido-4-(methylsulfanyl)butanoic acid
Traditional IUPAC Name:L-methionine, N-acetyl-
SMILES:[H][C@@](CCSC)(NC(C)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentMethionine and derivatives
Alternative Parents
Substituents
  • Methionine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Thia fatty acid
  • Fatty acid
  • Fatty acyl
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:105.5 C
Experimental Properties:
PropertyValueSource
Water Solubility:307mg/mL at 25oC [BEILSTEIN]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility6.84 g/LALOGPS
logP-0.15ALOGPS
logP-0.11ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity47.03 m³·mol⁻¹ChemAxon
Polarizability19.59 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Acetyl-CoA + L-Methionine > CoA + N-Acetyl-L-methionine
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0v4j-2920000000-21fd3a4d7b12ac2aca3cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0002-6900000000-3e9fc6c1775a4e3d390aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-c255d0240b6e3f4a5643View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006w-9310000000-580909b614389c497c25View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-006x-0900000000-e657a0db51c30ae3be19View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udl-1900000000-f56fad3e53b5ea9b2ecbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0002-9300000000-8202aca0e38266373acbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0005-1900000000-e28b73dfa967365c0250View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0f6x-3900000000-12868e3ab2754a2f9ee3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-137674c500bfd008d801View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-2900000000-8b99d2bc00227110da81View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9300000000-d8b36ea8efa070adb63eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0005-4900000000-f1e7e9d2f55dc3f8e191View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9300000000-bc39cc7c889e3f0d4390View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-012406ad4998287d85a8View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID165927
HMDB IDHMDB11745
Pubchem Compound ID448580
Kegg IDC02712
ChemSpider ID5945
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoAME

Enzymes

Protein Details
1. predicted acyltransferase with acyl-CoA N-acyltransferase domain
General function:
Not Available
Specific function:
Not Available
Gene Name:
yncA
Uniprot ID:
P76112
Molecular weight:
Not Available