N-Acetyl-L-methionine (PAMDB003432)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB003432
Identification
Name: N-Acetyl-L-methionine
Description:N-Acetyl-L-methionine is an acylated methionine derivative. The N-terminal methionine is often released from peptides and proteins in Pseudomonas aeruginosa 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
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 191.248
Monoisotopic Molecular Weight: 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:(2S)-2-acetamido-4-(methylsulfanyl)butanoic acid
Traditional IUPAC Name: N-acetylmethionine
SMILES:[H][C@@](CCSC)(NC(C)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as n-acyl-aliphatic-alpha amino acids. These are alpha amino acids carrying a N-acylated aliphatic chain.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent N-acyl-aliphatic-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-l-alpha-amino acid
  • Methionine or derivatives
  • Thia fatty acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Acetamide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic 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 mg/mLALOGPS
logP-0.15ALOGPS
logP-0.11ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity47.03 m3·mol-1ChemAxon
Polarizability19.59 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: 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 LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-15861132c8b2269198aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-2900000000-dfeda97a2049e74815ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w2m-9400000000-6da930234f6033225c78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0005-4900000000-fd1e8a8512a5adc4f78bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9500000000-ba3c2cf457f39b90d9b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-63ccb712a985eedfd16aView in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID21557
HMDB IDHMDB11745
Pubchem Compound ID448580
Kegg IDC02712
ChemSpider ID395338
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoAME

Enzymes

Protein Details
• predicted acyltransferase with acyl-CoA N-acyltransferase domain
General function:
Not Available
Specific function:
Not Available
Gene Name:
yncA
Locus Tag:
PA4866
Molecular weight:
18.7 kDa