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Record Information
Version3.6
Creation Date2013-06-15 18:06:23 UTC
Update Date2016-02-11 08:09:32 UTC
HMDB IDHMDB60623
Secondary Accession NumbersNone
Metabolite Identification
Common NamePerindopril Acyl-beta-D-glucuronide
DescriptionPerindopril Acyl-beta-D-glucuronide is a metabolite of perindopril. Perindopril, or perindopril arginine, (trade names include Coversyl and Aceon) is a long-acting ACE inhibitor. 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. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC25H40N2O11
Average Molecular Weight544.5919
Monoisotopic Molecular Weight544.263210132
IUPAC Name6-[(3aS,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name6-[(3aS,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]-octahydroindole-2-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CCC[C@H](N[C@@H](C)C(=O)N1[C@H]2CCCC[C@H]2CC1C(=O)OC1OC(C(O)C(O)C1O)C(O)=O)C(=O)OCC
InChI Identifier
InChI=1S/C25H40N2O11/c1-4-8-14(23(34)36-5-2)26-12(3)21(31)27-15-10-7-6-9-13(15)11-16(27)24(35)38-25-19(30)17(28)18(29)20(37-25)22(32)33/h12-20,25-26,28-30H,4-11H2,1-3H3,(H,32,33)/t12-,13-,14-,15-,16?,17?,18?,19?,20?,25?/m0/s1
InChI KeyInChIKey=VEYBPHDESXGJIN-VEYQHAJCSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha-amino acyl ester of carbohydrate
  • Alpha peptide
  • O-glucuronide
  • 1-o-glucuronide
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Glucuronic acid or derivatives
  • Alpha-amino acid ester
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Indole or derivatives
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine carboxylic acid
  • N-acylpyrrolidine
  • Fatty acid ester
  • Beta-hydroxy acid
  • Fatty acyl
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Saccharide
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Tertiary amine
  • Secondary alcohol
  • Polyol
  • Carboxylic acid ester
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Carboxylic acid
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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 Solubility7.95 mg/mLALOGPS
logP0.52ALOGPS
logP-1.7ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.13ChemAxon
pKa (Strongest Basic)5.47ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area192.16 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity127.99 m3·mol-1ChemAxon
Polarizability56.49 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
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 IDDBMET00984
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 LinkHMDB60623
Metagene LinkHMDB60623
METLIN IDNot Available
PubChem Compound45040207
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available