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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-24 14:03:25 UTC
Update Date2017-10-23 19:04:12 UTC
HMDB IDHMDB0004823
Secondary Accession Numbers
  • HMDB04823
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 Namelanthionine ketimine
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
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
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
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

  Organ and components:

Source:

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 Area86.96 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.49 m³·mol⁻¹ChemAxon
Polarizability16.74 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9500000000-309e1867d9ad6c4c2a13View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-9161000000-d8ad5bdcce13115f5542View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-5f1adeab0d59ee7b7becView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-4df44c76ec174857f040View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-6900000000-f8d2d44e0ed5f6587498View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-64c808af23378863affdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-5900000000-9e5b517823e0f4b6aa38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-8900000000-fc2f6a20e60563afee81View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Brain
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.0502 umol/mmol creatinineAdult (>18 years old)BothNormal details
    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
    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 ]