Record Information
Version3.6
Creation Date2006-08-24 14:03:25 UTC
Update Date2013-05-29 19:41:06 UTC
HMDB IDHMDB04823
Secondary Accession NumbersNone
Metabolite Identification
Common NameLanthionine ketimine
DescriptionLanthionine ketimine binds specifically and with high affinity to brain membranes and belong to a class of endogenous sulfur-containing cyclic products provided with a possible neurochemical function (PMID 1761027 ).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC6H7NO4S
Average Molecular Weight189.189
Monoisotopic Molecular Weight189.009578407
IUPAC Name3,6-dihydro-2H-1,4-thiazine-3,5-dicarboxylic acid
Traditional IUPAC Name3,6-dihydro-2H-1,4-thiazine-3,5-dicarboxylic acid
CAS Registry Number83923-11-9
SMILES
OC(=O)C1CSCC(=N1)C(O)=O
InChI Identifier
InChI=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
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassAlpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
Substituents
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Imine
  • Para Thiazine
  • Thioether
Direct ParentAlpha Amino Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 area86.96ChemAxon
rotatable bond count2ChemAxon
refractivity41.49ChemAxon
polarizability16.74ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Brain
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableCommentNormal
  • Not Applicable
UrineDetected and Quantified0.0502 umol/mmol creatinineAdult (>18 years old)BothNormal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023431
KNApSAcK IDNot Available
Chemspider ID118424
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04823
Metagene LinkHMDB04823
METLIN ID7085
PubChem Compound134340
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. Pubmed: 3254164
  2. 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. Pubmed: 1761027