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Record Information
StatusDetected and Quantified
Creation Date2006-05-22 14:17:32 UTC
Update Date2018-05-20 20:22:30 UTC
Secondary Accession Numbers
  • HMDB02015
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 ).
(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
InChI Identifier
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
  • 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 location:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility4.81 g/LALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06tf-9700000000-064a7f74e8121806f6faView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00gi-9231000000-0d483d0949f5f897af34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zg0-0950000000-64696a7adcffeb3a5cedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-a8ff5824ee63d1352a51View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-7900000000-033d092c5e8bbcc9c0e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0890000000-c0f2a88a27ab8992b871View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-9400000000-c6ee075b30d310a4c8c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9100000000-c356cce966bf5bc71bbdView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationNot Available
Normal Concentrations
BloodExpected but not Quantified Not AvailableNot Available
    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
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB022797
    KNApSAcK IDNot Available
    Chemspider ID119692
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID6438
    PubChem Compound135905
    PDB IDNot Available
    ChEBI IDNot Available
    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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:10708546 ]