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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:41 UTC
HMDB IDHMDB0014635
Secondary Accession Numbers
  • HMDB14635
Metabolite Identification
Common NameFosinopril
DescriptionFosinopril is a phosphinic acid-containing ester prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is rapidly hydrolyzed to fosinoprilat, its principle active metabolite. Fosinoprilat inhibits 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). Fosinopril may be used to treat mild to moderate hypertension, as an adjunct in the treatment of congestive heart failure, and to slow the rate of progression of renal disease in hypertensive individuals with diabetes mellitus and microalbuminuria or overt nephropathy.
Structure
Data?1582753201
Synonyms
ValueSource
(2S,4S)-4-Cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acidChEBI
(2S,4S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acidChEBI
(S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acidChEBI
(2S,4S)-4-Cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylateGenerator
(2S,4S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylateGenerator
(S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylateGenerator
Fosinopril sodiumHMDB
MonoprilHMDB
NewaceHMDB
Squibb brand OF fosinopril sodiumHMDB
StarilHMDB
Bristol-myers squibb brand OF fosinopril sodiumHMDB
DynacilHMDB
FosenoprilHMDB
Fosinopril, (1(s*(r*)),2 alpha,4 beta)-isomerHMDB
Fosinopril, (1(s*(s*)),2 alpha,4 beta)-isomerHMDB
FositensHMDB
Sanol brand OF fosinopril sodiumHMDB
Sodium, fosinoprilHMDB
TensocardilHMDB
Bristol myers squibb brand OF fosinopril sodiumHMDB
Ferrer brand OF fosinopril sodiumHMDB
FosinilHMDB
FosinormHMDB
Schwarz brand OF fosinopril sodiumHMDB
Esteve brand OF fosinopril sodiumHMDB
Fosinopril, (1(s*(r*)),2 alpha,4 alpha)-(D-pro)-isomerHMDB
FozitecHMDB
HiperlexHMDB
Merck lipha santé brand OF fosinoprilHMDB
Tenso stopHMDB
Chemical FormulaC30H46NO7P
Average Molecular Weight563.6625
Monoisotopic Molecular Weight563.301189343
IUPAC Name(2S,4S)-4-cyclohexyl-1-(2-{[2-methyl-1-(propanoyloxy)propoxy](4-phenylbutyl)phosphoryl}acetyl)pyrrolidine-2-carboxylic acid
Traditional Namefosinopril
CAS Registry Number98048-97-6
SMILES
CCC(=O)OC(OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N1C[C@@H](C[C@H]1C(O)=O)C1CCCCC1)C(C)C
InChI Identifier
InChI=1S/C30H46NO7P/c1-4-28(33)37-30(22(2)3)38-39(36,18-12-11-15-23-13-7-5-8-14-23)21-27(32)31-20-25(19-26(31)29(34)35)24-16-9-6-10-17-24/h5,7-8,13-14,22,24-26,30H,4,6,9-12,15-21H2,1-3H3,(H,34,35)/t25-,26+,30?,39?/m1/s1
InChI KeyBIDNLKIUORFRQP-FKDWWROVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentProline and derivatives
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Proline or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Carboxylic acid ester
  • Carboxamide group
  • Phosphinic acid ester
  • Organoheterocyclic compound
  • Carboxylic acid
  • Azacycle
  • Organophosphorus compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point149 - 153 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.001 g/LNot Available
LogP6.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.001 g/LALOGPS
logP4.71ALOGPS
logP5.49ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)3.87ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area110.21 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity149.12 m³·mol⁻¹ChemAxon
Polarizability61.17 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+230.35531661259
DarkChem[M-H]-219.40931661259
DeepCCS[M+H]+230.50130932474
DeepCCS[M-H]-228.40430932474
DeepCCS[M-2H]-261.64730932474
DeepCCS[M+Na]+236.70530932474
AllCCS[M+H]+229.932859911
AllCCS[M+H-H2O]+228.832859911
AllCCS[M+NH4]+231.032859911
AllCCS[M+Na]+231.232859911
AllCCS[M-H]-210.432859911
AllCCS[M+Na-2H]-213.232859911
AllCCS[M+HCOO]-216.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FosinoprilCCC(=O)OC(OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N1C[C@@H](C[C@H]1C(O)=O)C1CCCCC1)C(C)C4533.5Standard polar33892256
FosinoprilCCC(=O)OC(OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N1C[C@@H](C[C@H]1C(O)=O)C1CCCCC1)C(C)C3492.3Standard non polar33892256
FosinoprilCCC(=O)OC(OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N1C[C@@H](C[C@H]1C(O)=O)C1CCCCC1)C(C)C3978.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fosinopril,1TMS,isomer #1CCC(=O)OC(OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N1C[C@H](C2CCCCC2)C[C@H]1C(=O)O[Si](C)(C)C)C(C)C3894.7Semi standard non polar33892256
Fosinopril,1TBDMS,isomer #1CCC(=O)OC(OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N1C[C@H](C2CCCCC2)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)C(C)C4095.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Fosinopril GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9211610000-94f1646db6bff331382d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosinopril GC-MS (1 TMS) - 70eV, Positivesplash10-052f-9011161000-d47389b6092a1bdbc1082017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosinopril GC-MS ("Fosinopril,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosinopril GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Fosinopril LC-ESI-QTOF , negative-QTOFsplash10-014i-0000900000-f61a6a8a62cc0c92102b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fosinopril LC-ESI-QTOF , negative-QTOFsplash10-014i-0000900000-ed280398ec57e4a02dce2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fosinopril LC-ESI-QTOF , negative-QTOFsplash10-00di-0090300000-4e1c300644a39a64aefe2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fosinopril LC-ESI-QTOF , negative-QTOFsplash10-00di-0090000000-85f8c80f83290feea35c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fosinopril LC-ESI-QTOF , negative-QTOFsplash10-00di-0090000000-e28a43e299ff58e3a6bc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fosinopril LC-ESI-QFT , negative-QTOFsplash10-014i-0010900000-a142ed389f6652d197f12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fosinopril LC-ESI-QFT , negative-QTOFsplash10-00di-1090000000-833fa43a37b31e08737c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fosinopril LC-ESI-QFT , negative-QTOFsplash10-00di-1090000000-cda46913f10b57e392042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fosinopril LC-ESI-QFT , negative-QTOFsplash10-00di-2290000000-8627963d14d5d091e3382017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fosinopril LC-ESI-QFT , negative-QTOFsplash10-0229-7890000000-a5186e8ef5fa038d0a912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fosinopril LC-ESI-QFT , negative-QTOFsplash10-03k9-9720000000-ff0242177e3d4ef6c38a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fosinopril LC-ESI-QTOF , positive-QTOFsplash10-000f-0000900000-a2e65cd39ca7266f3a022017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fosinopril LC-ESI-QTOF , positive-QTOFsplash10-000i-0000900000-0eee13fe1a605e98c9852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fosinopril LC-ESI-QTOF , positive-QTOFsplash10-00ku-0105900000-1253dd1cea86dcfde7f62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fosinopril LC-ESI-QTOF , positive-QTOFsplash10-0udl-0908200000-59ff4955c6e6b2d364352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fosinopril LC-ESI-QTOF , positive-QTOFsplash10-0udi-0901000000-e2b0d1bb8bfd4d6f75952017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fosinopril LC-ESI-QFT , positive-QTOFsplash10-000i-0000900000-f625a00c8eb75cbf317d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fosinopril LC-ESI-QFT , positive-QTOFsplash10-0f6x-0409200000-5a18b8096c457898aa5f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fosinopril LC-ESI-QFT , positive-QTOFsplash10-0udi-0900000000-28e69824d7a0442561b62017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosinopril 10V, Positive-QTOFsplash10-052g-8501940000-1921bd0fb11f89e7ac6d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosinopril 20V, Positive-QTOFsplash10-0a4l-9742100000-b1fe493a8ecd28a1063b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosinopril 40V, Positive-QTOFsplash10-0006-9300100000-2565c33f04881158cfa22016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosinopril 10V, Negative-QTOFsplash10-0a4i-9001350000-645f2ba1f7eb05f66e9c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosinopril 20V, Negative-QTOFsplash10-0adj-8956210000-4bf1693483e47cacee672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosinopril 40V, Negative-QTOFsplash10-001a-1690000000-5349ec5626e3dd64f38d2016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 DB00492 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00492 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00492
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID50469
KEGG Compound IDC07016
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFosinopril
METLIN IDNot Available
PubChem Compound55891
PDB IDNot Available
ChEBI ID5163
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. Sharma S, Deitchman D, Eni JS, Gelperin K, Ilgenfritz JP, Blumenthal M: The hemodynamic effects of long-term ACE inhibition with fosinopril in patients with heart failure. Fosinopril Hemodynamics Study Group. Am J Ther. 1999 Jul;6(4):181-9. [PubMed:11329095 ]
  2. David D, Jallad N, Germino FW, Willett MS, de Silva J, Weidner SM, Mills DJ: A Comparison of the Cough Profile of Fosinopril and Enalapril in Hypertensive Patients with a History of ACE Inhibitor-Associated Cough. Am J Ther. 1995 Oct;2(10):806-813. [PubMed:11854791 ]

Enzymes

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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Ondetti MA: Structural relationships of angiotensin converting-enzyme inhibitors to pharmacologic activity. Circulation. 1988 Jun;77(6 Pt 2):I74-8. [PubMed:2836111 ]
  3. Piepho RW: Overview of the angiotensin-converting-enzyme inhibitors. Am J Health Syst Pharm. 2000 Oct 1;57 Suppl 1:S3-7. [PubMed:11030016 ]
  4. Sharma S, Deitchman D, Eni JS, Gelperin K, Ilgenfritz JP, Blumenthal M: The hemodynamic effects of long-term ACE inhibition with fosinopril in patients with heart failure. Fosinopril Hemodynamics Study Group. Am J Ther. 1999 Jul;6(4):181-9. [PubMed:11329095 ]

Transporters

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 ]