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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-15 16:49:50 UTC
Update Date2017-10-23 19:15:44 UTC
HMDB IDHMDB0060562
Secondary Accession Numbers
  • HMDB60562
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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity81.33 m³·mol⁻¹ChemAxon
Polarizability33.3 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, Positivesplash10-0006-9420000000-1e9f91d2d1efa46fc197View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03xs-8983200000-7b08be09237de09d0fc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014u-1498000000-092d5ab2e49b20b5f7baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00r6-5891000000-ccb01429cf0929d73fe8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00yu-9820000000-1e9aff4fc707a4070367View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f79-1596000000-98258469d8e47f11a7aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-2930000000-4af36cae664d5b02b289View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01w0-9520000000-32337ef8ce43c185983fView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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
      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