Lanthionine ketimine (CHEM021678)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:09:49 UTC
Update Date2016-11-09 01:17:20 UTC
Accession NumberCHEM021678
Identification
Common NameLanthionine ketimine
ClassSmall Molecule
DescriptionA member of the class of 1,4-thiazines that is 3,6-dihydro-2H-1,4-thiazine substituted by carboxy groups at positions 3 and 5. It is a natural but non-proteogenic amino acid found in human urine and brain.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,6-Dihydro-2H-1,4-thiazine-3,5-dicarboxylateHMDB
Lanthionine ketimineMeSH
Chemical FormulaC6H7NO4S
Average Molecular Mass189.189 g/mol
Monoisotopic Mass189.010 g/mol
CAS Registry Number83923-11-9
IUPAC Name3,6-dihydro-2H-1,4-thiazine-3,5-dicarboxylic acid
Traditional Namelanthionine ketimine
SMILESOC(=O)C1CSCC(=N1)C(O)=O
InChI IdentifierInChI=1S/C6H7NO4S/c8-5(9)3-1-12-2-4(7-3)6(10)11/h3H,1-2H2,(H,8,9)(H,10,11)
InChI KeyXIVVIYYWXOMYOD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Dicarboxylic acid or derivatives
  • Ketimine
  • Carboxylic acid
  • Thioether
  • Azacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Imine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.46 g/LALOGPS
logP-0.29ALOGPS
logP0.17ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.1ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.96 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.49 m³·mol⁻¹ChemAxon
Polarizability16.74 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9500000000-309e1867d9ad6c4c2a13Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-9161000000-d8ad5bdcce13115f5542Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-5f1adeab0d59ee7b7becSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-4df44c76ec174857f040Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-6900000000-f8d2d44e0ed5f6587498Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-64c808af23378863affdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-5900000000-9e5b517823e0f4b6aa38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-8900000000-fc2f6a20e60563afee81Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-b826da11214451de7764Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1900000000-306d71c7fd5fa967955bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c03-9000000000-fb202312621d19ddce70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-e2330d7ba32c7b65a991Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-4900000000-15070ec72d16fee1ba73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9000000000-1703a915eadd87796debSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004823
FooDB IDFDB023431
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-16728
METLIN ID7085
PDB IDNot Available
Wikipedia LinkLanthionine_ketimine
Chemspider ID118424
ChEBI ID89479
PubChem Compound ID134340
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1761027
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20181595
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20714314
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21271304
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24042198
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=28044206
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=29398540
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=29475037
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=3254164
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=8103986
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=9232634
12. Pecci L, Antonucci A, Nardini M, Cavallini D: Detection of cystathionine and lanthionine ketimines in human urine. Biochem Int. 1988 Nov;17(5):877-83.
13. Cavallini D, Ricci G, Dupre S, Pecci L, Costa M, Matarese RM, Pensa B, Antonucci A, Solinas SP, Fontana M: Sulfur-containing cyclic ketimines and imino acids. A novel family of endogenous products in the search for a role. Eur J Biochem. 1991 Dec 5;202(2):217-23.