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Record Information
Version3.6
Creation Date2006-05-22 14:17:32 UTC
Update Date2016-02-11 01:05:13 UTC
HMDB IDHMDB02015
Secondary Accession NumbersNone
Metabolite Identification
Common NameCystathionine ketimine
DescriptionD-cystathionine ketimine and L-cystathionine ketimine enhance superoxide generation by human neutrophils in a different manner. D-Cystathionine Ketimine enhanced seryl phosphorylation of 16. 5-kDa protein in human neutrophils, while L-Cystathionine Ketimine enhanced tyrosyl phosphorylation of 45-kDa protein.(PMID: 10049498 ). Among the cystathionine metabolites, cystathionine ketimine and N-acetyl-S-(3-oxo-3-carboxy-n-propyl) cysteine (NAc-OCPC) significantly enhanced the N-formylmethionylleucylphenylalanine (fMLP)-induced superoxide generation, but cystathionine, NAc-cystathionine, and cyclothionine did not enhance the superoxide generation. Cystathionine ketimine and NAc-OCPC also enhanced superoxide generation induced by opsonized zymosan (OZ) but not that induced by arachidonic acid (AA) and phorbol 12-myristate 13-acetate (PMA). Superoxide generation induced by cystathionine ketimine and NAc-OCPC was inhibited by genistein, an inhibitor of tyrosine kinase, and was enhanced by 1-(5-isoquinoline sulfonyl)-2-methylpiperazine (H-7), an inhibitor of protein kinase C.(PMID: 10708546 ).
Structure
Thumb
Synonyms
ValueSource
(5R)-2,5,6,7-tetrahydro-1,4-Thiazepine-3,5-dicarboxylic acidHMDB
Chemical FormulaC7H9NO4S
Average Molecular Weight203.216
Monoisotopic Molecular Weight203.025228471
IUPAC Name(5R)-2,5,6,7-tetrahydro-1,4-thiazepine-3,5-dicarboxylic acid
Traditional Namecystathionine ketimine
CAS Registry Number87254-95-3
SMILES
OC(=O)[C@H]1CCSCC(=N1)C(O)=O
InChI Identifier
InChI=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 KeyInChIKey=XJUQJVUYGRTQGI-SCSAIBSYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Azacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Thioether
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 Solubility4.81 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.2 m3·mol-1ChemAxon
Polarizability18.44 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified0.33 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 IDFDB022797
KNApSAcK IDNot Available
Chemspider ID119692
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02015
Metagene LinkHMDB02015
METLIN ID6438
PubChem Compound135905
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [8373176 ]
  2. 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. [3254164 ]
  3. 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. [2361849 ]
  4. 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. [10049498 ]
  5. 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. [10708546 ]