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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2014-06-23 10:26:39 UTC
Update Date2021-09-14 15:47:06 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
Physiological effectNot Available
DispositionNot Available
Process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+205.02931661259
DarkChem[M-H]-196.90331661259
DeepCCS[M+H]+200.63730932474
DeepCCS[M-H]-198.24130932474
DeepCCS[M-2H]-231.12530932474
DeepCCS[M+Na]+206.5530932474
AllCCS[M+H]+210.132859911
AllCCS[M+H-H2O]+208.232859911
AllCCS[M+NH4]+211.832859911
AllCCS[M+Na]+212.332859911
AllCCS[M-H]-201.432859911
AllCCS[M+Na-2H]-202.432859911
AllCCS[M+HCOO]-203.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TemocaprilCCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CS[C@@H](CN(CC(O)=O)C1=O)C1=CC=CS15465.2Standard polar33892256
TemocaprilCCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CS[C@@H](CN(CC(O)=O)C1=O)C1=CC=CS13208.5Standard non polar33892256
TemocaprilCCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CS[C@@H](CN(CC(O)=O)C1=O)C1=CC=CS13728.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Temocapril,1TMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C)C1=O3803.4Semi standard non polar33892256
Temocapril,1TMS,isomer #2CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O)C1=O)[Si](C)(C)C3787.8Semi standard non polar33892256
Temocapril,2TMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C)C1=O)[Si](C)(C)C3731.9Semi standard non polar33892256
Temocapril,2TMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C)C1=O)[Si](C)(C)C3516.8Standard non polar33892256
Temocapril,2TMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C)C1=O)[Si](C)(C)C4878.1Standard polar33892256
Temocapril,1TBDMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C(C)(C)C)C1=O4037.4Semi standard non polar33892256
Temocapril,1TBDMS,isomer #2CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O)C1=O)[Si](C)(C)C(C)(C)C3969.8Semi standard non polar33892256
Temocapril,2TBDMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C(C)(C)C)C1=O)[Si](C)(C)C(C)(C)C4111.3Semi standard non polar33892256
Temocapril,2TBDMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C(C)(C)C)C1=O)[Si](C)(C)C(C)(C)C3935.0Standard non polar33892256
Temocapril,2TBDMS,isomer #1CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C(C)(C)C)C1=O)[Si](C)(C)C(C)(C)C4887.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Temocapril GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3300900000-07c0bde728f9e7cad38a2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Temocapril GC-MS (1 TMS) - 70eV, Positivesplash10-004i-3200910000-b52f07bd2a96ae84f2c22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Temocapril GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Temocapril 10V, Positive-QTOFsplash10-0fmi-2900400000-06af7a1143b5abccba262017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Temocapril 20V, Positive-QTOFsplash10-003u-4362900000-0743a982c0ed45c1affb2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Temocapril 40V, Positive-QTOFsplash10-00du-9300000000-2585084c57fba4d3130f2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Temocapril 10V, Negative-QTOFsplash10-004i-2921400000-ea6d0202eb7b0a7b86b42017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Temocapril 20V, Negative-QTOFsplash10-004i-3953400000-eea8b567695e041631322017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Temocapril 40V, Negative-QTOFsplash10-00ej-9430000000-053ca4271d92f5f59f9d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Temocapril 10V, Positive-QTOFsplash10-004i-0000900000-55f39eb3922a0c1c8f262021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Temocapril 20V, Positive-QTOFsplash10-004i-0511900000-9d098ce150dd0dd4ee3e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Temocapril 40V, Positive-QTOFsplash10-08ir-0790000000-ef9ad031ca41af6d886f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Temocapril 10V, Negative-QTOFsplash10-004i-0000900000-2c8feffe734e85cdc0852021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Temocapril 20V, Negative-QTOFsplash10-00fr-1091400000-22c4735d269f91570e2a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Temocapril 40V, Negative-QTOFsplash10-01zi-1490100000-9fff467ed2cf416a6dce2021-09-24Wishart LabView Spectrum
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 IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available