Cystathionine ketimine (CHEM021674)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:09:42 UTC
Update Date2016-11-09 01:17:20 UTC
Accession NumberCHEM021674
Identification
Common NameCystathionine ketimine
ClassSmall Molecule
DescriptionA 1-thia-4-azacyclohepta-3-ene-3,5-dicarboxylic acid that has R-configuration. It is cyclic sulfur-containing imino acid detected in bovine brain extracts.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5R)-1-Thia-4-azacyclohepta-3-ene-3,5-dicarboxylic acidChEBI
(R)-2,5,6,7-Tetrahydro-1,4-thiazepine-3,5-dicarboxylic acidChEBI
(5R)-1-Thia-4-azacyclohepta-3-ene-3,5-dicarboxylateGenerator
(R)-2,5,6,7-Tetrahydro-1,4-thiazepine-3,5-dicarboxylateGenerator
(5R)-2,5,6,7-tetrahydro-1,4-Thiazepine-3,5-dicarboxylic acidHMDB
(5R)-2,5,6,7-Tetrahydro-1,4-thiazepine-3,5-dicarboxylateGenerator, HMDB
Cystathionine ketimineMeSH
CTHMDB
Chemical FormulaC7H9NO4S
Average Molecular Mass203.216 g/mol
Monoisotopic Mass203.025 g/mol
CAS Registry Number87254-95-3
IUPAC Name(5R)-2,5,6,7-tetrahydro-1,4-thiazepine-3,5-dicarboxylic acid
Traditional Namecystathionine ketimine
SMILESOC(=O)[C@H]1CCSCC(=N1)C(O)=O
InChI IdentifierInChI=1S/C7H9NO4S/c9-6(10)4-1-2-13-3-5(8-4)7(11)12/h4H,1-3H2,(H,9,10)(H,11,12)/t4-/m1/s1
InChI KeyXJUQJVUYGRTQGI-SCSAIBSYSA-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 Solubility4.81 g/LALOGPS
logP-0.09ALOGPS
logP0.39ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)-2.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.96 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.2 m³·mol⁻¹ChemAxon
Polarizability18.44 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06tf-9700000000-064a7f74e8121806f6faSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00gi-9231000000-0d483d0949f5f897af34Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zg0-0950000000-64696a7adcffeb3a5cedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-a8ff5824ee63d1352a51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-7900000000-033d092c5e8bbcc9c0e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0890000000-c0f2a88a27ab8992b871Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-9400000000-c6ee075b30d310a4c8c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9100000000-c356cce966bf5bc71bbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0190000000-ad3fce9f1c62485e5f99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-4960000000-dca64cdeb75732fe6feeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03ec-9700000000-3d7fee60c01c76320079Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0290000000-15e3b2bb631cedd301e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-1950000000-67f23b8d22dafbc89095Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0229-9200000000-717072248046ae2e0ddbSpectrum
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 IDHMDB0002015
FooDB IDFDB022797
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-16729
METLIN ID6438
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID119692
ChEBI ID90001
PubChem Compound ID135905
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=10049498
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10708546
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=10954021
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15698597
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22001859
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=2213011
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=2361849
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=2393402
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24190565
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=3254164
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=4026871
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=6878413
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=8373176
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=8573164
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=8713134
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=9232634
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=9781627
18. Okada T, Takechi T, Wakiguchi H, Kurashige T, Sugahara K, Kodama H: Identification of new cystathionine mono-oxo acids, S-(3-oxo-3-carboxy-n-propyl) cysteine and S-(2-oxo-2-carboxyethyl) homocysteine, in the urine of a patient with cystathioninuria. Arch Biochem Biophys. 1993 Sep;305(2):385-91.
19. 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.
20. Antonucci A, Pecci L, Fontana M, Cavallini D: Influence of diet on cystathionine ketimine and lanthionine ketimine content in human urine. Ital J Biochem. 1990 Mar-Apr;39(2):100-5.
21. Zhang J, Zhang M, Sugahara K, Sagara Y, Spirito A, Dupre, Kodama H: D-cystathionine ketimine and L-cystathionine ketimine enhance superoxide generation by human neutrophils in a different manner. Arch Biochem Biophys. 1999 Mar 1;363(1):55-9.
22. Kodama H, Zhang J, Sugahara K: Novel priming compounds of cystathionine metabolites on superoxide generation in human neutrophils. Biochem Biophys Res Commun. 2000 Mar 16;269(2):297-301.