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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2014-06-23 10:26:39 UTC
Update Date2019-07-23 07:17:04 UTC
HMDB IDHMDB0061720
Secondary Accession Numbers
  • HMDB61720
Metabolite Identification
Common NameTemocapril
DescriptionTemocapril belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Temocapril is a very strong basic compound (based on its pKa). In humans, temocapril is involved in temocapril metabolism pathway. Temocapril can also be used in hemodialysis patients without risk of serious accumulation. When compared with other Angiotensin-converting Enzyme Inhibitors, temocapril's advantages include a rapid onset of action and what research suggests is tighter vascular ACE binding than enalaprilat. ACE inhibitors exert their hemodynamic effect mainly by inhibiting the renin-angiotensin system. Temocaprilat has slightly higher potency than enalaprilat in ACE inhibition isolated from rabbit lung. Temocapril is a prodrug-type angiotensin-I converting enzyme (ACE) inhibitor not approved for use in the United States, but is approved in Japan and South Korea. Temocapril is a prodrug of its active metabolite (and diacid form) temocaprilat which contains a thiazepine ring. They cause mainly vasodilation and mild natriuresis without affecting heart rate and contractility. They also modulate sympathetic nervous system activity and increase prostaglandin synthesis.
Structure
Data?1563866223
Synonyms
ValueSource
alpha-((2S,6R)-6-((1S)-1-Ethoxycarbonyl-3-phenylpropyl)amino-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepin-4-yl)acetic acid.hclHMDB
Temocapril hydrochlorideHMDB
Chemical FormulaC23H28N2O5S2
Average Molecular Weight476.609
Monoisotopic Molecular Weight476.143963396
IUPAC Name2-[(2S,6R)-6-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-5-oxo-2-(thiophen-2-yl)-1,4-thiazepan-4-yl]acetic acid
Traditional Name[(2S,6R)-6-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-5-oxo-2-(thiophen-2-yl)-1,4-thiazepan-4-yl]acetic acid
CAS Registry NumberNot Available
SMILES
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CS[C@@H](CN(CC(O)=O)C1=O)C1=CC=CS1
InChI Identifier
InChI=1S/C23H28N2O5S2/c1-2-30-23(29)17(11-10-16-7-4-3-5-8-16)24-18-15-32-20(19-9-6-12-31-19)13-25(22(18)28)14-21(26)27/h3-9,12,17-18,20,24H,2,10-11,13-15H2,1H3,(H,26,27)/t17-,18-,20-/m0/s1
InChI KeyFIQOFIRCTOWDOW-BJLQDIEVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Alpha-amino acid ester
  • Alpha-amino acid or derivatives
  • Fatty acid ester
  • Aralkylamine
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Thiophene
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid ester
  • Amino acid
  • Lactam
  • Secondary amine
  • Dialkylthioether
  • Organoheterocyclic compound
  • Azacycle
  • Thioether
  • Carboxylic acid
  • Secondary aliphatic amine
  • Organooxygen compound
  • Organic oxide
  • Amine
  • Organic oxygen compound
  • Carbonyl group
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

Role

Industrial application:

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 Solubility0.0034 g/LALOGPS
logP2.46ALOGPS
logP2.04ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)3.88ChemAxon
pKa (Strongest Basic)5.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.94 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity124.1 m³·mol⁻¹ChemAxon
Polarizability49.28 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3300900000-07c0bde728f9e7cad38aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-3200910000-b52f07bd2a96ae84f2c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fmi-2900400000-06af7a1143b5abccba26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003u-4362900000-0743a982c0ed45c1affbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00du-9300000000-2585084c57fba4d3130fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2921400000-ea6d0202eb7b0a7b86b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-3953400000-eea8b567695e04163132Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ej-9430000000-053ca4271d92f5f59f9dSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08836
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTemocapril
METLIN IDNot Available
PubChem Compound443874
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available