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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2016-10-26 22:25:03 UTC
Update Date2021-09-14 15:46:12 UTC
HMDB IDHMDB0062182
Secondary Accession Numbers
  • HMDB62182
Metabolite Identification
Common NameN-lactoyl-Methionine
DescriptionN-lactoyl-Methionine is lactoyl derivative of methionine. N-lactoyl-amino acids are ubiquitous pseudodipeptides of lactic acid and amino acids that are rapidly formed by reverse proteolysis. A protease, cytosolic nonspecific dipeptidase 2 (CNDP2), catalyzes their formation. The plasma levels of these metabolites strongly correlate with plasma levels of lactate and amino acid. (PMID: 25964343 )
Structure
Data?1563866276
SynonymsNot Available
Chemical FormulaC8H15NO4S
Average Molecular Weight221.27
Monoisotopic Molecular Weight221.072179141
IUPAC Name2-[(2S)-2-hydroxypropanamido]-4-(methylsulfanyl)butanoic acid
Traditional Name2-[(2S)-2-hydroxypropanamido]-4-(methylsulfanyl)butanoic acid
CAS Registry NumberNot Available
SMILES
CSCCC(NC(=O)[C@H](C)O)C(O)=O
InChI Identifier
InChI=1S/C8H15NO4S/c1-5(10)7(11)9-6(8(12)13)3-4-14-2/h5-6,10H,3-4H2,1-2H3,(H,9,11)(H,12,13)/t5-,6?/m0/s1
InChI KeyUFMNJPDGXQPVJM-ZBHICJROSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Hydroxy fatty acid
  • Thia fatty acid
  • Fatty acid
  • Fatty acyl
  • Secondary alcohol
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Thioether
  • Sulfenyl compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Dialkylthioether
  • Organooxygen compound
  • Organonitrogen compound
  • Organosulfur compound
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-0.69ALOGPS
logP-0.36ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.92ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity53.23 m³·mol⁻¹ChemAxon
Polarizability22.25 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+150.3430932474
DeepCCS[M-H]-146.82230932474
DeepCCS[M-2H]-183.15230932474
DeepCCS[M+Na]+158.90630932474
AllCCS[M+H]+149.432859911
AllCCS[M+H-H2O]+146.132859911
AllCCS[M+NH4]+152.532859911
AllCCS[M+Na]+153.432859911
AllCCS[M-H]-147.932859911
AllCCS[M+Na-2H]-149.232859911
AllCCS[M+HCOO]-150.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-lactoyl-MethionineCSCCC(NC(=O)[C@H](C)O)C(O)=O3176.5Standard polar33892256
N-lactoyl-MethionineCSCCC(NC(=O)[C@H](C)O)C(O)=O1737.8Standard non polar33892256
N-lactoyl-MethionineCSCCC(NC(=O)[C@H](C)O)C(O)=O1918.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-lactoyl-Methionine,1TMS,isomer #1CSCCC(NC(=O)[C@H](C)O[Si](C)(C)C)C(=O)O1879.2Semi standard non polar33892256
N-lactoyl-Methionine,1TMS,isomer #2CSCCC(NC(=O)[C@H](C)O)C(=O)O[Si](C)(C)C1856.8Semi standard non polar33892256
N-lactoyl-Methionine,1TMS,isomer #3CSCCC(C(=O)O)N(C(=O)[C@H](C)O)[Si](C)(C)C1843.4Semi standard non polar33892256
N-lactoyl-Methionine,2TMS,isomer #1CSCCC(NC(=O)[C@H](C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1937.2Semi standard non polar33892256
N-lactoyl-Methionine,2TMS,isomer #2CSCCC(C(=O)O)N(C(=O)[C@H](C)O[Si](C)(C)C)[Si](C)(C)C1925.4Semi standard non polar33892256
N-lactoyl-Methionine,2TMS,isomer #3CSCCC(C(=O)O[Si](C)(C)C)N(C(=O)[C@H](C)O)[Si](C)(C)C1875.1Semi standard non polar33892256
N-lactoyl-Methionine,3TMS,isomer #1CSCCC(C(=O)O[Si](C)(C)C)N(C(=O)[C@H](C)O[Si](C)(C)C)[Si](C)(C)C1970.5Semi standard non polar33892256
N-lactoyl-Methionine,3TMS,isomer #1CSCCC(C(=O)O[Si](C)(C)C)N(C(=O)[C@H](C)O[Si](C)(C)C)[Si](C)(C)C1940.6Standard non polar33892256
N-lactoyl-Methionine,3TMS,isomer #1CSCCC(C(=O)O[Si](C)(C)C)N(C(=O)[C@H](C)O[Si](C)(C)C)[Si](C)(C)C2073.4Standard polar33892256
N-lactoyl-Methionine,1TBDMS,isomer #1CSCCC(NC(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)C(=O)O2132.9Semi standard non polar33892256
N-lactoyl-Methionine,1TBDMS,isomer #2CSCCC(NC(=O)[C@H](C)O)C(=O)O[Si](C)(C)C(C)(C)C2104.7Semi standard non polar33892256
N-lactoyl-Methionine,1TBDMS,isomer #3CSCCC(C(=O)O)N(C(=O)[C@H](C)O)[Si](C)(C)C(C)(C)C2082.0Semi standard non polar33892256
N-lactoyl-Methionine,2TBDMS,isomer #1CSCCC(NC(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2416.2Semi standard non polar33892256
N-lactoyl-Methionine,2TBDMS,isomer #2CSCCC(C(=O)O)N(C(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2406.0Semi standard non polar33892256
N-lactoyl-Methionine,2TBDMS,isomer #3CSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](C)O)[Si](C)(C)C(C)(C)C2355.7Semi standard non polar33892256
N-lactoyl-Methionine,3TBDMS,isomer #1CSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2651.8Semi standard non polar33892256
N-lactoyl-Methionine,3TBDMS,isomer #1CSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2558.3Standard non polar33892256
N-lactoyl-Methionine,3TBDMS,isomer #1CSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2480.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-lactoyl-Methionine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9200000000-fb8859f7570dbefed0f52017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-lactoyl-Methionine GC-MS (2 TMS) - 70eV, Positivesplash10-014i-7941000000-94aa4d9feac3619b4dc92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-lactoyl-Methionine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-lactoyl-Methionine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-lactoyl-Methionine 10V, Positive-QTOFsplash10-0fk9-2790000000-6dbafbe2d31899a71d8b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-lactoyl-Methionine 20V, Positive-QTOFsplash10-0ufr-4920000000-799b56141a9e1b2678572017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-lactoyl-Methionine 40V, Positive-QTOFsplash10-0udi-7900000000-35771f1eab0f5a013e502017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-lactoyl-Methionine 10V, Negative-QTOFsplash10-00dj-8590000000-754e1a9b2cfcc7a0184a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-lactoyl-Methionine 20V, Negative-QTOFsplash10-0002-9210000000-235b1178fdbb7b6b45872017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-lactoyl-Methionine 40V, Negative-QTOFsplash10-0002-9000000000-427fb93ebfaaa92922d22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-lactoyl-Methionine 10V, Negative-QTOFsplash10-00di-0090000000-9994357b10d8773d21e42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-lactoyl-Methionine 20V, Negative-QTOFsplash10-0002-9100000000-564d61cb00638e9786b92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-lactoyl-Methionine 40V, Negative-QTOFsplash10-0002-9000000000-e1d92d2a30bee517d7542021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-lactoyl-Methionine 10V, Positive-QTOFsplash10-0udi-0930000000-f58a5c9195e9e85f3ae32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-lactoyl-Methionine 20V, Positive-QTOFsplash10-0udi-1900000000-5d9d04849cf14f9361f22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-lactoyl-Methionine 40V, Positive-QTOFsplash10-03di-9100000000-0154f817e660197717eb2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131770418
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jansen RS, Addie R, Merkx R, Fish A, Mahakena S, Bleijerveld OB, Altelaar M, IJlst L, Wanders RJ, Borst P, van de Wetering K: N-lactoyl-amino acids are ubiquitous metabolites that originate from CNDP2-mediated reverse proteolysis of lactate and amino acids. Proc Natl Acad Sci U S A. 2015 May 26;112(21):6601-6. doi: 10.1073/pnas.1424638112. Epub 2015 May 11. [PubMed:25964343 ]