Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110629
Identification
Name: N-formyl-L-methionine
Description:The conjugate base of N-formyl-L-methionine; major species at pH 7.3.
Structure
Thumb
Synonyms:
  • fMet
  • N-formyl-methionine
  • formylmethionine
Chemical Formula: C6H10NO3S
Average Molecular Weight: 176.21
Monoisotopic Molecular Weight: 177.0459639146
InChI Key: PYUSHNKNPOHWEZ-YFKPBYRVSA-M
InChI: InChI=1S/C6H11NO3S/c1-11-3-2-5(6(9)10)7-4-8/h4-5H,2-3H2,1H3,(H,7,8)(H,9,10)/p-1/t5-/m0/s1
CAS number: 4289-98-9
IUPAC Name:(2S)-2-formamido-4-(methylsulfanyl)butanoate
Traditional IUPAC Name: N-formylmethionine
SMILES:C(=O)NC(CCSC)C(=O)[O-]
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as methionine and derivatives. These 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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct Parent Methionine and derivatives
Alternative Parents
Substituents
  • Methionine or derivatives
  • N-formyl-alpha-amino acid
  • N-formyl-alpha amino acid or derivatives
  • Thia fatty acid
  • Fatty acyl
  • Fatty acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Thioether
  • Sulfenyl compound
  • Dialkylthioether
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.75 mg/mLALOGPS
logP-0.61ALOGPS
logP-0.16ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.93ChemAxon
pKa (Strongest Basic)-0.91ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity42.54 m3·mol-1ChemAxon
Polarizability17.46 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0fb9-0900000000-4beb911575f3b3d2f1eaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03e9-9000000000-c2c1d1013bdc15802a84View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-9000000000-9dae6c72fe61c0d106d9View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Sherriff RM, Broom MF, Chadwick VS: Isolation and purification of N-formylmethionine aminopeptidase from rat intestine. Biochim Biophys Acta. 1992 Mar 12;1119(3):275-80. [1547272 ]
Synthesis Reference: Milligan D L; Koshland D E Jr The amino terminus of the aspartate chemoreceptor is formylmethionine. The Journal of biological chemistry (1990), 265(8), 4455-60.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CAS4289-98-9
ChEBI57809
DrugBankDB04464
HMDBHMDB01015
KEGGC03145
PubChem25244433