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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:47:17 UTC
Update Date2021-09-14 15:40:14 UTC
HMDB IDHMDB0041908
Secondary Accession Numbers
  • HMDB41908
Metabolite Identification
Common NameImidaprilat
DescriptionImidaprilat, is the active metabolite of Imidapril. Imidapril is a prodrug used to treat hypertension, chronic congestive heart failure (CHF), acute myocardial infarction (AMI), and diabetic nephropathy (PMID: 17547476 ,18192036 ,12177688 , 17094051 ). Imidapril belongs to a class of long-acting, non-sulfhydryl angiotensin-converting enzyme (ACE) inhibitors (PMID: 8851752 , 12177688 ). Imidaprilat competitively binds and inhibits the catalytic activity of ACE, which results in a reduction of peripheral resistance and a reduction in systemic blood pressure (BP) (PMID: 17547476 ). Imidaprilat is only found in individuals that have used or taken imidapril.
Structure
Data?1563863713
Synonyms
ValueSource
(4S)-1-Methyl-3-{(2S)-2-[N-((1S)-1-carboxy-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylic acidChEBI
ImidaprilateChEBI
ImidaprilatumChEBI
(4S)-1-Methyl-3-{(2S)-2-[N-((1S)-1-carboxy-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylateGenerator
Imidaprilic acidGenerator
6366aHMDB
Imidaprilat, (4S-(3(R(r*)),4R*))-isomerHMDB
Imidaprilat, monosodium salt, (4S-(3(r*(r*)),4R*))-isomerHMDB
3-(2-(N-(1-Carboxy-3-phenylpropyl)amino)propionyl)-1-methyl-2-oxoimidazolidine-4-carboxylic acidHMDB
Imidaprilat hydrochloride, (4S-(3(r*(r*)),4R*))HMDB
Imidaprilat hydrochloride, (4S-(3(s*(r*)),4R*))-isomerHMDB
Chemical FormulaC18H23N3O6
Average Molecular Weight377.3917
Monoisotopic Molecular Weight377.158685483
IUPAC Name(4S)-3-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-1-methyl-2-oxoimidazolidine-4-carboxylic acid
Traditional Name(4S)-3-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-1-methyl-2-oxoimidazolidine-4-carboxylic acid
CAS Registry Number89371-44-8
SMILES
[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(O)=O)C(=O)N1C(=O)N(C)C[C@@]1([H])C(O)=O
InChI Identifier
InChI=1S/C18H23N3O6/c1-11(15(22)21-14(17(25)26)10-20(2)18(21)27)19-13(16(23)24)9-8-12-6-4-3-5-7-12/h3-7,11,13-14,19H,8-10H2,1-2H3,(H,23,24)(H,25,26)/t11-,13-,14-/m0/s1
InChI KeyVFAVNRVDTAPBNR-UBHSHLNASA-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-l-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • N-acyl urea
  • Aralkylamine
  • Ureide
  • Imidazolidinone
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Dicarboximide
  • Imidazolidine
  • Urea
  • Amino acid
  • Amino acid or derivatives
  • Carbonic acid derivative
  • Carboxylic acid
  • Secondary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
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 ID4576629
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkImidapril
METLIN IDNot Available
PubChem Compound5464344
PDB IDNot Available
ChEBI ID141520
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. Yamanaka K, Morikawa S, Murata K, Banno K, Sato T, Takai T, Suzuki T, Mizobe M, Ito M, Ishibashi K: Radioimmunoassay for imidapril, a new angiotensin-converting enzyme inhibitor, and imidaprilat, its active metabolite, in human plasma and urine. J Pharm Biomed Anal. 1996 Jan;14(3):281-7. [PubMed:8851752 ]
  2. Hosoya K, Ishimitsu T: Protection of the cardiovascular system by imidapril, a versatile angiotensin-converting enzyme inhibitor. Cardiovasc Drug Rev. 2002 Summer;20(2):93-110. doi: 10.1111/j.1527-3466.2002.tb00185.x. [PubMed:12177688 ]
  3. Robinson DM, Curran MP, Lyseng-Williamson KA: Imidapril: a review of its use in essential hypertension, Type 1 diabetic nephropathy and chronic heart failure. Drugs. 2007;67(9):1359-78. doi: 10.2165/00003495-200767090-00008. [PubMed:17547476 ]
  4. Dolezal T: Imidapril in heart failure. J Renin Angiotensin Aldosterone Syst. 2006 Sep;7(3):146-54. doi: 10.3317/jraas.2006.024. [PubMed:17094051 ]
  5. Guo XG, Uzui H, Mizuguchi T, Ueda T, Chen JZ, Lee JD: Imidaprilat inhibits matrix metalloproteinase-2 activity in human cardiac fibroblasts induced by interleukin-1beta via NO-dependent pathway. Int J Cardiol. 2008 Jun 6;126(3):414-20. doi: 10.1016/j.ijcard.2007.08.134. Epub 2008 Jan 14. [PubMed:18192036 ]