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Record Information
Version3.6
Creation Date2013-06-15 16:49:50 UTC
Update Date2017-03-02 22:05:13 UTC
HMDB IDHMDB60562
Secondary Accession NumbersNone
Metabolite Identification
Common NameCaptopril-cysteine disulfide
DescriptionCaptopril-cysteine disulfide is a metabolite of captopril. Captopril is an angiotensin-converting enzyme inhibitor used for the treatment of hypertension and some types of congestive heart failure. Captopril was the first ACE inhibitor developed and was considered a breakthrough both because of its novel mechanism of action and also because of the revolutionary development process. Captopril is commonly marketed by Bristol-Myers Squibb under the trade name Capoten. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
Captopril-cysteine disulfideMeSH
Captopril-L-cysteineMeSH
Chemical FormulaC12H20N2O5S2
Average Molecular Weight336.428
Monoisotopic Molecular Weight336.08136314
IUPAC Name(2S)-1-[(2S)-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}-2-methylpropanoyl]pyrrolidine-2-carboxylic acid
Traditional Name(2S)-1-[(2S)-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}-2-methylpropanoyl]pyrrolidine-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
C[C@H](CSSC[C@H](N)C(O)=O)C(=O)N1CCC[C@H]1C(O)=O
InChI Identifier
InChI=1S/C12H20N2O5S2/c1-7(5-20-21-6-8(13)11(16)17)10(15)14-4-2-3-9(14)12(18)19/h7-9H,2-6,13H2,1H3,(H,16,17)(H,18,19)/t7-,8+,9+/m1/s1
InChI KeyNEEBNBLVYKFVTK-VGMNWLOBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as l-cysteine-s-conjugates. These are compounds containing L-cysteine where the thio-group is conjugated.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentL-cysteine-S-conjugates
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Proline or derivatives
  • L-cysteine-s-conjugate
  • L-alpha-amino acid
  • Alpha-amino acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine carboxylic acid
  • N-acylpyrrolidine
  • Dicarboxylic acid or derivatives
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Carboxamide group
  • Amino acid
  • Dialkyldisulfide
  • Organic disulfide
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Primary amine
  • Primary aliphatic amine
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.53 mg/mLALOGPS
logP-1.5ALOGPS
logP-2.4ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.81ChemAxon
pKa (Strongest Basic)9.04ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area120.93 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity81.33 m3·mol-1ChemAxon
Polarizability33.3 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00803
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB60562
      Metagene LinkHMDB60562
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available