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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-15 17:03:38 UTC
Update Date2021-09-14 15:40:14 UTC
HMDB IDHMDB0060579
Secondary Accession Numbers
  • HMDB60579
Metabolite Identification
Common NameRamiprilat
DescriptionRamiprilat, also known as ramiprilic acid, 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. Ramiprilat is a very strong basic compound (based on its pKa). In humans, ramiprilat is involved in ramipril metabolism pathway. Ramiprilat is a metabolite of ramipril.
Structure
Data?1563866078
Synonyms
ValueSource
RamiprilateChEBI
RamiprilatumChEBI
Ramiprilic acidGenerator
Chemical FormulaC21H28N2O5
Average Molecular Weight388.4574
Monoisotopic Molecular Weight388.199822016
IUPAC Name(2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-octahydrocyclopenta[b]pyrrole-2-carboxylic acid
Traditional Name(2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
C[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1[C@H]2CCC[C@H]2C[C@H]1C(O)=O
InChI Identifier
InChI=1S/C21H28N2O5/c1-13(22-16(20(25)26)11-10-14-6-3-2-4-7-14)19(24)23-17-9-5-8-15(17)12-18(23)21(27)28/h2-4,6-7,13,15-18,22H,5,8-12H2,1H3,(H,25,26)(H,27,28)/t13-,15-,16-,17-,18-/m0/s1
InChI KeyKEDYTOTWMPBSLG-HILJTLORSA-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
  • N-acyl-alpha-amino acid
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine carboxylic acid
  • N-acylpyrrolidine
  • Aralkylamine
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Organoheterocyclic compound
  • Azacycle
  • Secondary aliphatic amine
  • Carboxylic acid
  • Secondary amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Process

Naturally occurring process

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 Solubility0.21 g/LALOGPS
logP0.54ALOGPS
logP-0.18ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.13ChemAxon
pKa (Strongest Basic)8.05ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.94 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity101.67 m³·mol⁻¹ChemAxon
Polarizability40.37 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]+190.03931661259
DarkChem[M-H]-183.76231661259
DeepCCS[M+H]+187.20130932474
DeepCCS[M-H]-184.80630932474
DeepCCS[M-2H]-217.68930932474
DeepCCS[M+Na]+193.11430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
RamiprilatC[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1[C@H]2CCC[C@H]2C[C@H]1C(O)=O4654.5Standard polar33892256
RamiprilatC[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1[C@H]2CCC[C@H]2C[C@H]1C(O)=O2962.9Standard non polar33892256
RamiprilatC[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1[C@H]2CCC[C@H]2C[C@H]1C(O)=O3199.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ramiprilat,1TMS,isomer #1C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)N1[C@H](C(=O)O)C[C@@H]2CCC[C@@H]213046.2Semi standard non polar33892256
Ramiprilat,1TMS,isomer #2C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O)C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCC[C@@H]213073.5Semi standard non polar33892256
Ramiprilat,1TMS,isomer #3C[C@@H](C(=O)N1[C@H](C(=O)O)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C3050.3Semi standard non polar33892256
Ramiprilat,2TMS,isomer #1C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCC[C@@H]213035.6Semi standard non polar33892256
Ramiprilat,2TMS,isomer #2C[C@@H](C(=O)N1[C@H](C(=O)O)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C3020.2Semi standard non polar33892256
Ramiprilat,2TMS,isomer #3C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C3023.7Semi standard non polar33892256
Ramiprilat,3TMS,isomer #1C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C3038.0Semi standard non polar33892256
Ramiprilat,3TMS,isomer #1C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C3015.3Standard non polar33892256
Ramiprilat,3TMS,isomer #1C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C3781.8Standard polar33892256
Ramiprilat,1TBDMS,isomer #1C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1[C@H](C(=O)O)C[C@@H]2CCC[C@@H]213294.4Semi standard non polar33892256
Ramiprilat,1TBDMS,isomer #2C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O)C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCC[C@@H]213320.8Semi standard non polar33892256
Ramiprilat,1TBDMS,isomer #3C[C@@H](C(=O)N1[C@H](C(=O)O)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C3309.7Semi standard non polar33892256
Ramiprilat,2TBDMS,isomer #1C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCC[C@@H]213505.8Semi standard non polar33892256
Ramiprilat,2TBDMS,isomer #2C[C@@H](C(=O)N1[C@H](C(=O)O)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3527.6Semi standard non polar33892256
Ramiprilat,2TBDMS,isomer #3C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C3540.5Semi standard non polar33892256
Ramiprilat,3TBDMS,isomer #1C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3732.7Semi standard non polar33892256
Ramiprilat,3TBDMS,isomer #1C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3608.3Standard non polar33892256
Ramiprilat,3TBDMS,isomer #1C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3996.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ramiprilat GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lu-9323000000-940b006da9cc06b5fc6f2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ramiprilat GC-MS (2 TMS) - 70eV, Positivesplash10-01bc-9141420000-7b066a10b282ca0372032017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ramiprilat 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 - Ramiprilat 10V, Positive-QTOFsplash10-05g3-0129000000-f89fdd99fb3669abd1432017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ramiprilat 20V, Positive-QTOFsplash10-0btc-1953000000-dfe1ab2c8f9ea43b55d92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ramiprilat 40V, Positive-QTOFsplash10-08fu-3910000000-087ef0850acdcd1f8f502017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ramiprilat 10V, Negative-QTOFsplash10-000l-0009000000-b5af622fa6177501b3e12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ramiprilat 20V, Negative-QTOFsplash10-0frg-0649000000-fd1f4001ead8c583d80b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ramiprilat 40V, Negative-QTOFsplash10-11p0-1900000000-0b5f7e804738b6a5e86d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ramiprilat 10V, Negative-QTOFsplash10-000i-0009000000-e43abe228ffb93ba92512021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ramiprilat 20V, Negative-QTOFsplash10-01q3-1946000000-d8f9fa67c21f695490902021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ramiprilat 40V, Negative-QTOFsplash10-0udi-3910000000-7248ba42f7d521ea892f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ramiprilat 10V, Positive-QTOFsplash10-000i-0009000000-8ffcb38a7676a96d10df2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ramiprilat 20V, Positive-QTOFsplash10-01p6-1935000000-2b66e2a4796a046c7eff2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ramiprilat 40V, Positive-QTOFsplash10-066r-1900000000-13f50f12fb869bbe2aaa2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
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 Compound5464096
PDB IDNot Available
ChEBI ID77363
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. Gupta VK, Jain R, Lukram O, Agarwal S, Dwivedi A: Simultaneous determination of ramipril, ramiprilat and telmisartan in human plasma using liquid chromatography tandem mass spectrometry. Talanta. 2011 Jan 15;83(3):709-16. doi: 10.1016/j.talanta.2010.10.011. Epub 2010 Nov 18. [PubMed:21147310 ]
  2. Efsen E, Saermark T, Hansen A, Bruun E, Brynskov J: Ramiprilate inhibits functional matrix metalloproteinase activity in Crohn's disease fistulas. Basic Clin Pharmacol Toxicol. 2011 Sep;109(3):208-16. doi: 10.1111/j.1742-7843.2011.00713.x. Epub 2011 Jun 3. [PubMed:21535409 ]
  3. Potier L, Waeckel L, Vincent MP, Chollet C, Gobeil F Jr, Marre M, Bruneval P, Richer C, Roussel R, Alhenc-Gelas F, Bouby N: Selective kinin receptor agonists as cardioprotective agents in myocardial ischemia and diabetes. J Pharmacol Exp Ther. 2013 Jul;346(1):23-30. doi: 10.1124/jpet.113.203927. Epub 2013 Apr 16. [PubMed:23591995 ]
  4. van Griensven JM, Schoemaker RC, Cohen AF, Luus HG, Seibert-Grafe M, Rothig HJ: Pharmacokinetics, pharmacodynamics and bioavailability of the ACE inhibitor ramipril. Eur J Clin Pharmacol. 1995;47(6):513-8. [PubMed:7768254 ]