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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:47 UTC
HMDB IDHMDB0014928
Secondary Accession Numbers
  • HMDB14928
Metabolite Identification
Common NamePerindopril
DescriptionPerindopril is a nonsulfhydryl prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is rapidly metabolized in the liver to perindoprilat, its active metabolite, following oral administration. Perindoprilat is a potent, competitive inhibitor of ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Perindopril may be used to treat mild to moderate essential hypertension, mild to moderate congestive heart failure, and to reduce the cardiovascular risk of individuals with hypertension or post-myocardial infarction and stable coronary disease.
Structure
Data?1582753236
Synonyms
ValueSource
(2S,3AS,7as)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]octahydro-1H-indole-2-carboxylic acidChEBI
PerindoprilumChEBI
(2S,3AS,7as)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]octahydro-1H-indole-2-carboxylateGenerator
Perindopril erbumineHMDB
Erbumine, perindoprilHMDB
PerstariumHMDB
PirindoprilHMDB
Chemical FormulaC19H32N2O5
Average Molecular Weight368.4678
Monoisotopic Molecular Weight368.231122144
IUPAC Name(2S,3aS,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid
Traditional Nameperindopril
CAS Registry Number107133-36-8
SMILES
[H][C@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@@]1([H])CCCC2)C(O)=O
InChI Identifier
InChI=1S/C19H32N2O5/c1-4-8-14(19(25)26-5-2)20-12(3)17(22)21-15-10-7-6-9-13(15)11-16(21)18(23)24/h12-16,20H,4-11H2,1-3H3,(H,23,24)/t12-,13-,14-,15-,16-/m0/s1
InChI KeyIPVQLZZIHOAWMC-QXKUPLGCSA-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
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Indole or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine carboxylic acid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid ester
  • Amino acid
  • Azacycle
  • Secondary aliphatic amine
  • Carboxylic acid
  • Organoheterocyclic compound
  • Secondary amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.22 g/LNot Available
LogP2.6Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available188.771http://allccs.zhulab.cn/database/detail?ID=AllCCS00001290
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.22 g/LALOGPS
logP0.56ALOGPS
logP0.63ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.79ChemAxon
pKa (Strongest Basic)5.48ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.94 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity95.69 m³·mol⁻¹ChemAxon
Polarizability40 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+188.75131661259
DarkChem[M-H]-184.53631661259
DeepCCS[M-2H]-228.00830932474
DeepCCS[M+Na]+203.43130932474
AllCCS[M+H]+191.332859911
AllCCS[M+H-H2O]+188.932859911
AllCCS[M+NH4]+193.432859911
AllCCS[M+Na]+194.032859911
AllCCS[M-H]-189.932859911
AllCCS[M+Na-2H]-190.532859911
AllCCS[M+HCOO]-191.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Perindopril[H][C@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@@]1([H])CCCC2)C(O)=O3582.5Standard polar33892256
Perindopril[H][C@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@@]1([H])CCCC2)C(O)=O2511.1Standard non polar33892256
Perindopril[H][C@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@@]1([H])CCCC2)C(O)=O2643.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Perindopril,1TMS,isomer #1CCC[C@H](N[C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCCC[C@@H]21)C(=O)OCC2502.7Semi standard non polar33892256
Perindopril,1TMS,isomer #2CCC[C@@H](C(=O)OCC)N([C@@H](C)C(=O)N1[C@H](C(=O)O)C[C@@H]2CCCC[C@@H]21)[Si](C)(C)C2559.8Semi standard non polar33892256
Perindopril,2TMS,isomer #1CCC[C@@H](C(=O)OCC)N([C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCCC[C@@H]21)[Si](C)(C)C2584.6Semi standard non polar33892256
Perindopril,2TMS,isomer #1CCC[C@@H](C(=O)OCC)N([C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCCC[C@@H]21)[Si](C)(C)C2626.8Standard non polar33892256
Perindopril,2TMS,isomer #1CCC[C@@H](C(=O)OCC)N([C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCCC[C@@H]21)[Si](C)(C)C3568.4Standard polar33892256
Perindopril,1TBDMS,isomer #1CCC[C@H](N[C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCCC[C@@H]21)C(=O)OCC2732.6Semi standard non polar33892256
Perindopril,1TBDMS,isomer #2CCC[C@@H](C(=O)OCC)N([C@@H](C)C(=O)N1[C@H](C(=O)O)C[C@@H]2CCCC[C@@H]21)[Si](C)(C)C(C)(C)C2801.4Semi standard non polar33892256
Perindopril,2TBDMS,isomer #1CCC[C@@H](C(=O)OCC)N([C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCCC[C@@H]21)[Si](C)(C)C(C)(C)C3034.6Semi standard non polar33892256
Perindopril,2TBDMS,isomer #1CCC[C@@H](C(=O)OCC)N([C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCCC[C@@H]21)[Si](C)(C)C(C)(C)C3015.9Standard non polar33892256
Perindopril,2TBDMS,isomer #1CCC[C@@H](C(=O)OCC)N([C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCCC[C@@H]21)[Si](C)(C)C(C)(C)C3687.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Perindopril GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-9432000000-cd5a3e77250a4c168d5f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perindopril GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-9717300000-83b70572a2f77f254c1f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perindopril GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Perindopril 10V, Positive-QTOFsplash10-014i-0009000000-c0f0dd0396757c3cf0ce2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perindopril 30V, Positive-QTOFsplash10-00dj-7900000000-6fb82e41c5f7509bf2d92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perindopril 20V, Positive-QTOFsplash10-00di-0911000000-bcbd5878353663a0becf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perindopril 40V, Positive-QTOFsplash10-0002-9100000000-b7ff9447b924f0855be02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perindopril 30V, Positive-QTOFsplash10-00dj-7900000000-06fd81d1ed4113d2cced2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perindopril 20V, Positive-QTOFsplash10-00di-1900000000-5c07491310faaef3dcb52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perindopril 40V, Positive-QTOFsplash10-0002-9100000000-f50db0738e177a8967422021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perindopril 10V, Positive-QTOFsplash10-014i-0309000000-24875256bb05cbaf71422021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Perindopril 50V, Positive-QTOFsplash10-0002-9000000000-4d9452d99f15221077722021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perindopril 10V, Positive-QTOFsplash10-00xr-0419000000-0e51e0565dc0448212142016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perindopril 20V, Positive-QTOFsplash10-00di-2911000000-f881afe8478f809812e52016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perindopril 40V, Positive-QTOFsplash10-00dj-7900000000-499eef769e6c62234d002016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perindopril 10V, Negative-QTOFsplash10-00xr-1019000000-651b3131d4943a27d13d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perindopril 20V, Negative-QTOFsplash10-00xs-3869000000-63563bd6f1750d029d0c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perindopril 40V, Negative-QTOFsplash10-01ba-7920000000-49269668d5fb9b6e35b22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perindopril 10V, Positive-QTOFsplash10-014i-0109000000-4e9eb37e2b101ab0d3282021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perindopril 20V, Positive-QTOFsplash10-0092-2933000000-3aebf3a627740b77e5ad2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perindopril 40V, Positive-QTOFsplash10-00di-8900000000-f0eeabeb32b9b945d9e82021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perindopril 10V, Negative-QTOFsplash10-014i-0009000000-75ed3bac35742770931b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perindopril 20V, Negative-QTOFsplash10-0v6r-2932000000-efd1b65151e2c1476ba72021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perindopril 40V, Negative-QTOFsplash10-014i-1901000000-b8ee2f14b02c83d2d9212021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00790 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00790 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00790
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID96956
KEGG Compound IDC07706
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPerindopril
METLIN IDNot Available
PubChem Compound107807
PDB IDNot Available
ChEBI ID8024
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 References
  1. Yoshiji H, Kuriyama S, Kawata M, Yoshii J, Ikenaka Y, Noguchi R, Nakatani T, Tsujinoue H, Fukui H: The angiotensin-I-converting enzyme inhibitor perindopril suppresses tumor growth and angiogenesis: possible role of the vascular endothelial growth factor. Clin Cancer Res. 2001 Apr;7(4):1073-8. [PubMed:11309359 ]
  2. Hurst M, Jarvis B: Perindopril: an updated review of its use in hypertension. Drugs. 2001;61(6):867-96. [PubMed:11398915 ]
  3. Simpson D, Noble S, Goa KL: Perindopril: in congestive heart failure. Drugs. 2002;62(9):1367-77; discussion 1378-9. [PubMed:12076191 ]
  4. Yasumatsu R, Nakashima T, Masuda M, Ito A, Kuratomi Y, Nakagawa T, Komune S: Effects of the angiotensin-I converting enzyme inhibitor perindopril on tumor growth and angiogenesis in head and neck squamous cell carcinoma cells. J Cancer Res Clin Oncol. 2004 Oct;130(10):567-73. Epub 2004 Jul 27. [PubMed:15449186 ]
  5. Jastrzebskal M, Widecka K, Naruszewicz M, Ciechanowicz A, Janczak-Bazan A, Foltynska A, Goracy I, Chetstowski K, Wesotowska T: Effects of perindopril treatment on hemostatic function in patients with essential hypertension in relation to angiotensin converting enzyme (ACE) and plasminogen activator inhibitor-1 (PAI-1) gene polymorphisms. Nutr Metab Cardiovasc Dis. 2004 Oct;14(5):259-69. [PubMed:15673060 ]
  6. Parker E, Aarons L, Rowland M, Resplandy G: The pharmacokinetics of perindoprilat in normal volunteers and patients: influence of age and disease state. Eur J Pharm Sci. 2005 Sep;26(1):104-13. [PubMed:15982858 ]

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575
References
  1. Mehta A, Iyer L, Parmar S, Shah G, Goyal R: Oculohypotensive effect of perindopril in acute and chronic models of glaucoma in rabbits. Can J Physiol Pharmacol. 2010 May;88(5):595-600. doi: 10.1139/y10-026. [PubMed:20555429 ]
General function:
Involved in metallopeptidase activity
Specific function:
Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent vasodilator. Has also a glycosidase activity which releases GPI-anchored proteins from the membrane by cleaving the mannose linkage in the GPI moiety
Gene Name:
ACE
Uniprot ID:
P12821
Molecular weight:
149713.7
References
  1. Alfakih K, Hall AS: Perindopril. Expert Opin Pharmacother. 2006 Jan;7(1):63-71. [PubMed:16370923 ]
  2. Brugts JJ, Ferrari R, Simoons ML: Angiotensin-converting enzyme inhibition by perindopril in the treatment of cardiovascular disease. Expert Rev Cardiovasc Ther. 2009 Apr;7(4):345-60. doi: 10.1586/erc.09.2. [PubMed:19379059 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  4. Song JC, White CM: Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update. Clin Pharmacokinet. 2002;41(3):207-24. [PubMed:11929321 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Takara K, Kakumoto M, Tanigawara Y, Funakoshi J, Sakaeda T, Okumura K: Interaction of digoxin with antihypertensive drugs via MDR1. Life Sci. 2002 Feb 15;70(13):1491-500. [PubMed:11895100 ]
General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular weight:
78805.3
References
  1. Knutter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M: Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. [PubMed:18713951 ]
General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:
SLC15A2
Uniprot ID:
Q16348
Molecular weight:
81782.8
References
  1. Knutter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M: Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. [PubMed:18713951 ]