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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:04:15 UTC
Update Date2019-07-23 07:15:15 UTC
HMDB IDHMDB0060863
Secondary Accession Numbers
  • HMDB60863
Metabolite Identification
Common NamePerindoprilat glucuronide
DescriptionPerindoprilat glucuronide belongs to the class of organic compounds known as depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids), commonly but not necessarily regularly alternating. Perindopril, or perindopril arginine, (trade names include Coversyl and Aceon) is a long-acting ACE inhibitor. Perindoprilat glucuronide is a very strong basic compound (based on its pKa). Perindoprilat glucuronide is a metabolite of perindopril. In humans, perindoprilat glucuronide is involved in perindopril action pathway. Perindopril is used to treat high blood pressure, heart failure or stable coronary artery disease. It is also available in a generic form, perindopril erbumine.
Structure
Data?1563866115
SynonymsNot Available
Chemical FormulaC23H36N2O11
Average Molecular Weight516.5387
Monoisotopic Molecular Weight516.231910004
IUPAC Name(2R,3R,4S,5S,6R)-2-[(2S,3aS,7aS)-1-{2-[(1-carboxypropyl)amino]propanoyl}-octahydro-1H-indole-2-carbonyloxy]-3,4,5-trihydroxy-6-methyloxane-2-carboxylic acid
Traditional Name(2R,3R,4S,5S,6R)-2-[(2S,3aS,7aS)-1-{2-[(1-carboxypropyl)amino]propanoyl}-octahydroindole-2-carbonyloxy]-3,4,5-trihydroxy-6-methyloxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CCC(NC(C)C(=O)N1[C@H]2CCCC[C@H]2C[C@H]1C(=O)O[C@@]1(O[C@H](C)[C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C23H36N2O11/c1-4-13(20(30)31)24-10(2)19(29)25-14-8-6-5-7-12(14)9-15(25)21(32)36-23(22(33)34)18(28)17(27)16(26)11(3)35-23/h10-18,24,26-28H,4-9H2,1-3H3,(H,30,31)(H,33,34)/t10?,11-,12+,13?,14+,15+,16-,17+,18-,23-/m1/s1
InChI KeyDCYRDAKXQLERQS-FQCHSDBKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids), commonly but not necessarily regularly alternating.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassDepsipeptides
Direct ParentDepsipeptides
Alternative Parents
Substituents
  • Depsipeptide
  • Alpha-amino acyl ester of carbohydrate
  • Alpha-amino acid ester
  • Glucuronic acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Hexose monosaccharide
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Indole or derivatives
  • Tricarboxylic acid or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Ketal
  • Beta-hydroxy acid
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Secondary alcohol
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid ester
  • Amino acid
  • Secondary amine
  • Polyol
  • Acetal
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Carboxylic acid
  • Secondary aliphatic amine
  • Azacycle
  • Oxacycle
  • Carbonyl group
  • Organonitrogen compound
  • Alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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 Solubility4 g/LALOGPS
logP-0.33ALOGPS
logP-2.5ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
pKa (Strongest Basic)7.78ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area203.16 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity118.8 m³·mol⁻¹ChemAxon
Polarizability50.96 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9221100000-f04d8168a6bc6034d5b7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001r-9351012000-e478dd5dbd44d6d3df1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0arv-2739420000-e890e8000b397df7d26dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1933000000-401d708b3322006cb524Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f8c-5910000000-0a7fd00a34e46e5e6e7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-4913200000-afada72090bafecd6539Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a7r-3964200000-caf5c2ee484e65297262Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-6921000000-fc7ffdeaf8d3e2ce6ba9Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
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 Compound179962
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