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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:04:34 UTC
Update Date2019-07-23 07:15:16 UTC
HMDB IDHMDB0060869
Secondary Accession Numbers
  • HMDB60869
Metabolite Identification
Common NameRamipril Diketopiperazine
DescriptionRamipril Diketopiperazine is a metabolite of ramipril. Ramipril is an angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressure and congestive heart failure. It is marketed as Prilace by Arrow Pharmaceuticals in Australia, Ramipro by Westfield Pharma in the Philippines, Tritace by Sanofi-Aventis in Italy and United States and Altace by King Pharmaceuticals in the United States, Ramitens by PharmaSwiss, Ampril by Krka in Slovenia, Corpril by Cemelog-BRS in Hungary, Piramil and Prilinda by Hemofarm in Serbia, by Lek in Poland and by Novartis in Bangladesh, and in Canada as Altace (Sonfi) and Ramipril (Pharmascience). (Wikipedia)
Structure
Data?1563866116
SynonymsNot Available
Chemical FormulaC23H30N2O4
Average Molecular Weight398.4953
Monoisotopic Molecular Weight398.220557458
IUPAC Nameethyl (2S)-2-[(2S,6S,8S,11S)-11-methyl-9,12-dioxo-1,10-diazatricyclo[6.4.0.0²,⁶]dodecan-10-yl]-4-phenylbutanoate
Traditional Nameethyl (2S)-2-[(2S,6S,8S,11S)-11-methyl-9,12-dioxo-1,10-diazatricyclo[6.4.0.0²,⁶]dodecan-10-yl]-4-phenylbutanoate
CAS Registry NumberNot Available
SMILES
CCOC(=O)[C@H](CCC1=CC=CC=C1)N1[C@@H](C)C(=O)N2[C@H]3CCC[C@H]3C[C@H]2C1=O
InChI Identifier
InChI=1S/C23H30N2O4/c1-3-29-23(28)19(13-12-16-8-5-4-6-9-16)24-15(2)21(26)25-18-11-7-10-17(18)14-20(25)22(24)27/h4-6,8-9,15,17-20H,3,7,10-14H2,1-2H3/t15-,17-,18-,19-,20-/m0/s1
InChI KeyKOVMAAYRBJCASY-JBDAPHQKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid esters
Alternative Parents
Substituents
  • Alpha-amino acid ester
  • Dioxopiperazine
  • 2,5-dioxopiperazine
  • Fatty acid ester
  • N-alkylpiperazine
  • Monocyclic benzene moiety
  • 1,4-diazinane
  • Piperazine
  • Benzenoid
  • Fatty acyl
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Carboxamide group
  • Carboxylic acid ester
  • Lactam
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

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 Solubility0.2 g/LALOGPS
logP2.47ALOGPS
logP2.91ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)19.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.92 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity108.11 m³·mol⁻¹ChemAxon
Polarizability44.27 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-004i-5309000000-2afcfb697215cb9cda27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-1f728b746605d158e1a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fgn-2239000000-2094826fe233bc122d80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ec-9710000000-34a3c7ab049a258735feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0009000000-62b15887eb38e4d7cd6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-4797000000-d74c13f086dd40a7389cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kfy-9740000000-9fd225213e54ad3b8bb0Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
      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 LinkNot Available
      METLIN IDNot Available
      PubChem Compound14520363
      PDB IDNot Available
      ChEBI IDNot Available
      Food Biomarker OntologyNot Available
      VMH IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available