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Record Information
Version3.6
Creation Date2013-06-15 16:49:50 UTC
Update Date2016-02-11 08:08:22 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
SynonymsNot Available
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=1/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+/s2
InChI KeyInChIKey=NEEBNBLVYKFVTK-PQCSWJAFNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • 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
  • Dialkyldisulfide
  • Tertiary amine
  • Organic disulfide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • 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 QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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