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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-15 17:07:22 UTC
Update Date2021-09-14 15:40:14 UTC
HMDB IDHMDB0060583
Secondary Accession Numbers
  • HMDB60583
Metabolite Identification
Common NameTrandolaprilat
DescriptionTrandolaprilat 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. It is marketed by Abbott Laboratories with the brand name Mavik. Trandolaprilat is a very strong basic compound (based on its pKa). In humans, trandolaprilat is involved in trandolapril metabolism pathway. Trandolapril is an ACE inhibitor used to treat high blood pressure, it may also be used to treat other conditions. Trandolaprilat is a metabolite of trandolapril.
Structure
Data?1563866078
Synonyms
ValueSource
1-(2-((1-Carboxy-3-phenylpropyl)amino)-1-oxopropyl)octahydro-1H-indole-2-carboxylic acidHMDB
Trandolaprilat, (2S-(1R*(r*)),2alpha,3aalpha,7abeta)-isomerHMDB
TrandolaprilateHMDB
Trandolaprilat, (2S-(1(s*(r*)),2alpha,3aalpha,7abeta))-isomerHMDB
Trandolaprilat, (2S-(1(r*(r*)),2alpha,3abeta,7abeta))-isomerHMDB
Chemical FormulaC22H30N2O5
Average Molecular Weight402.484
Monoisotopic Molecular Weight402.21547208
IUPAC Name(2S,3aR,7aS)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid
Traditional Name(2S,3aR,7aS)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-octahydroindole-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]2CCCC[C@@H]2C[C@H]1C(O)=O
InChI Identifier
InChI=1S/C22H30N2O5/c1-14(23-17(21(26)27)12-11-15-7-3-2-4-8-15)20(25)24-18-10-6-5-9-16(18)13-19(24)22(28)29/h2-4,7-8,14,16-19,23H,5-6,9-13H2,1H3,(H,26,27)(H,28,29)/t14-,16+,17-,18-,19-/m0/s1
InChI KeyAHYHTSYNOHNUSH-HXFGRODQSA-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-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Indole or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary amine
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Organonitrogen compound
  • Amine
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.083 g/LALOGPS
logP0.77ALOGPS
logP0.19ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)3.13ChemAxon
pKa (Strongest Basic)8.04ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.94 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity106.27 m³·mol⁻¹ChemAxon
Polarizability42.91 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]+192.83831661259
DarkChem[M-H]-190.47231661259
DeepCCS[M+H]+189.53530932474
DeepCCS[M-H]-187.13930932474
DeepCCS[M-2H]-220.02230932474
DeepCCS[M+Na]+195.44730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TrandolaprilatC[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1[C@H]2CCCC[C@@H]2C[C@H]1C(O)=O4403.4Standard polar33892256
TrandolaprilatC[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1[C@H]2CCCC[C@@H]2C[C@H]1C(O)=O3001.6Standard non polar33892256
TrandolaprilatC[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1[C@H]2CCCC[C@@H]2C[C@H]1C(O)=O3291.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Trandolaprilat,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]2CCCC[C@@H]213027.8Semi standard non polar33892256
Trandolaprilat,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]2CCCC[C@@H]213056.7Semi standard non polar33892256
Trandolaprilat,1TMS,isomer #3C[C@@H](C(=O)N1[C@H](C(=O)O)C[C@H]2CCCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C3102.7Semi standard non polar33892256
Trandolaprilat,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]2CCCC[C@@H]213017.6Semi standard non polar33892256
Trandolaprilat,2TMS,isomer #2C[C@@H](C(=O)N1[C@H](C(=O)O)C[C@H]2CCCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C3047.9Semi standard non polar33892256
Trandolaprilat,2TMS,isomer #3C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@H]2CCCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C3061.4Semi standard non polar33892256
Trandolaprilat,3TMS,isomer #1C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@H]2CCCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C3080.5Semi standard non polar33892256
Trandolaprilat,3TMS,isomer #1C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@H]2CCCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C3123.0Standard non polar33892256
Trandolaprilat,3TMS,isomer #1C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@H]2CCCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C3954.7Standard polar33892256
Trandolaprilat,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]2CCCC[C@@H]213297.6Semi standard non polar33892256
Trandolaprilat,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]2CCCC[C@@H]213315.5Semi standard non polar33892256
Trandolaprilat,1TBDMS,isomer #3C[C@@H](C(=O)N1[C@H](C(=O)O)C[C@H]2CCCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C3354.5Semi standard non polar33892256
Trandolaprilat,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]2CCCC[C@@H]213489.7Semi standard non polar33892256
Trandolaprilat,2TBDMS,isomer #2C[C@@H](C(=O)N1[C@H](C(=O)O)C[C@H]2CCCC[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)C3547.7Semi standard non polar33892256
Trandolaprilat,2TBDMS,isomer #3C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2CCCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C3557.8Semi standard non polar33892256
Trandolaprilat,3TBDMS,isomer #1C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2CCCC[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)C3742.8Semi standard non polar33892256
Trandolaprilat,3TBDMS,isomer #1C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2CCCC[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)C3717.6Standard non polar33892256
Trandolaprilat,3TBDMS,isomer #1C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2CCCC[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)C4134.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Trandolaprilat GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-9527000000-a643d41bd64e07adba5a2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trandolaprilat GC-MS (2 TMS) - 70eV, Positivesplash10-00su-9222430000-0069ccf8184bd033698c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trandolaprilat 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 - Trandolaprilat 10V, Positive-QTOFsplash10-0k9i-0239400000-ab8bb14e56c9f83e8e162017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trandolaprilat 20V, Positive-QTOFsplash10-0a4i-1953000000-fdf35cfce0f13a2da0fa2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trandolaprilat 40V, Positive-QTOFsplash10-08ml-3910000000-249f7038306c9dfa5c022017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trandolaprilat 10V, Negative-QTOFsplash10-0zfr-0009500000-926c6ad77a5d3f549f5b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trandolaprilat 20V, Negative-QTOFsplash10-0rl0-0519100000-4bede66895662526d8302017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trandolaprilat 40V, Negative-QTOFsplash10-01b9-1900000000-99dcb0b8ac33262690fd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trandolaprilat 10V, Positive-QTOFsplash10-0udi-0004900000-86ea00e1726806b2e12c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trandolaprilat 20V, Positive-QTOFsplash10-0r6r-1924100000-8ec17a909156436e97bd2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trandolaprilat 40V, Positive-QTOFsplash10-014i-2900000000-aff52d5f6fcb564c63052021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trandolaprilat 10V, Negative-QTOFsplash10-0udi-0003900000-aa8d32acfe381a17f46b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trandolaprilat 20V, Negative-QTOFsplash10-0ue9-1942300000-0b762c05765866d551562021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trandolaprilat 40V, Negative-QTOFsplash10-0i03-3900000000-6b6ee1d22a0b4eb4677a2021-10-12Wishart 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 Compound5464097
PDB IDX93
ChEBI IDNot Available
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 ReferencesNot Available