Fosinopril (CED0006103)

Record Information

Version

1.0

Creation Date

2016-05-25 18:20:46 UTC

Update Date

2026-05-14 16:40:21 UTC

Accession Number

CHEM022119

Identification

Common Name

Fosinopril

Class

Small Molecule

Description

Fosinopril is an organic compound with the chemical formula C30H46NO7P. Fosinopril belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. With an average molecular weight of 563.66 g/mol, Fosinopril is a heavy molecule. This compound acts as an inhibitor of the protein target Angiotensin-converting enzyme (ACE). It is utilized within healthcare, pharmaceuticals, and veterinary products as an ACE inhibitor. Fosinopril is also found in or released from electrical and electronic equipment, specifically antennas, still video cameras, and electrically stimulated smoking devices. The recorded route of exposure for this substance is oral.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,4S)-4-Cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid	ChEBI
(2S,4S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acid	ChEBI
(S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acid	ChEBI
(2S,4S)-4-Cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylate	Generator
(2S,4S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylate	Generator
(S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylate	Generator
Fosinopril sodium	HMDB
Monopril	HMDB
Newace	HMDB
Squibb brand OF fosinopril sodium	HMDB
Staril	HMDB
Bristol-myers squibb brand OF fosinopril sodium	HMDB
Dynacil	HMDB
Fosenopril	HMDB
Fosinopril, (1(s(r)),2 alpha,4 beta)-isomer	HMDB
Fosinopril, (1(s(s)),2 alpha,4 beta)-isomer	HMDB
Fositens	HMDB
Sanol brand OF fosinopril sodium	HMDB
Sodium, fosinopril	HMDB
Tensocardil	HMDB
Bristol myers squibb brand OF fosinopril sodium	HMDB
Ferrer brand OF fosinopril sodium	HMDB
Fosinil	HMDB
Fosinorm	HMDB
Schwarz brand OF fosinopril sodium	HMDB
Esteve brand OF fosinopril sodium	HMDB
Fosinopril, (1(s(r)),2 alpha,4 alpha)-(D-pro)-isomer	HMDB
Fozitec	HMDB
Hiperlex	HMDB
Merck lipha santé brand OF fosinopril	HMDB
Tenso stop	HMDB

Chemical Formula

C₃₀H₄₆NO₇P

Average Molecular Mass

563.663 g/mol

Monoisotopic Mass

563.301 g/mol

CAS Registry Number

98048-97-6

IUPAC Name

(2S,4S)-4-cyclohexyl-1-(2-{[2-methyl-1-(propanoyloxy)propoxy](4-phenylbutyl)phosphoryl}acetyl)pyrrolidine-2-carboxylic acid

Traditional Name

fosinopril

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 Key

BIDNLKIUORFRQP-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Proline 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

L-proline derivative (CHEBI:5163 )
phosphinic ester (CHEBI:5163 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.001 g/L	ALOGPS
logP	4.71	ALOGPS
logP	5.49	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	110.21 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	149.12 m³·mol⁻¹	ChemAxon
Polarizability	61.17 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0006-9211610000-94f1646db6bff331382d	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-052f-9011161000-d47389b6092a1bdbc108	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0000900000-f61a6a8a62cc0c92102b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0000900000-ed280398ec57e4a02dce	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0090300000-4e1c300644a39a64aefe	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0090000000-85f8c80f83290feea35c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0090000000-e28a43e299ff58e3a6bc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0010900000-a142ed389f6652d197f1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-1090000000-833fa43a37b31e08737c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-1090000000-cda46913f10b57e39204	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-2290000000-8627963d14d5d091e338	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0229-7890000000-a5186e8ef5fa038d0a91	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03k9-9720000000-ff0242177e3d4ef6c38a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000f-0000900000-a2e65cd39ca7266f3a02	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0000900000-0eee13fe1a605e98c985	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00ku-0105900000-1253dd1cea86dcfde7f6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udl-0908200000-59ff4955c6e6b2d36435	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0901000000-e2b0d1bb8bfd4d6f7595	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0000900000-f625a00c8eb75cbf317d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0f6x-0409200000-5a18b8096c457898aa5f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0900000000-28e69824d7a0442561b6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0900000000-aa95f5f65aec2f92a48a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-2900000000-48b3327e8691a43ae029	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-6900000000-de8ad752f1c8f05aded2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0923000000-63e09411e5108e693e5b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ue9-0921000000-aff089cc0c53c0098919	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0090000000-e28a43e299ff58e3a6bc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0000900000-f61a6a8a62cc0c92102b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0000900000-ed280398ec57e4a02dce	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0090000000-85f8c80f83290feea35c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0090300000-4e1c300644a39a64aefe	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0000900000-63cb3ee1dc4a51a77cc9	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-1090000000-0c791ddb760c4285f84f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-1090000000-d91bec80632b35682297	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0010900000-c81ff030482abb1dad28	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0900000000-1b6ada00bc5264233819	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0f6x-0409200000-fc512665519ee66b1ae6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0000900000-ee695f160c97a9cc0035	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000f-0000900000-fd18ca1e06848ee30c4d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00ku-0105900000-d95b12c529e492860827	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udl-0908200000-3ddbc432db9a2ed8cbbd	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-003r-0910000000-0726d68552cf0c476c0f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00nr-0830900000-48042e8669c1bee16561	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0901000000-2d988759e8a68950cbf9	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000f-0000900000-d1b113cfd66ae9e2d14d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052g-8501940000-1921bd0fb11f89e7ac6d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4l-9742100000-b1fe493a8ecd28a1063b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9300100000-2565c33f04881158cfa2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-9001350000-645f2ba1f7eb05f66e9c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0adj-8956210000-4bf1693483e47cacee67	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001a-1690000000-5349ec5626e3dd64f38d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03e9-0020590000-cd73b13b52f638582327	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0089-3431900000-0d8814ddab723074d86b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002b-0920000000-ccad80da7e887dbfae5e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0020920000-99b02ce809885a44a55e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0195700000-0c05b02c1e95d886dc2f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ab9-9110000000-5f12deae45d294c2333c	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
832.0	Log mg/kg	[470:1500]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
295	ACE inhibitors	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
534	Still Video Cameras	Electrical & Electronic Equipment	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available

Pathways

4 pathways

Fosinopril Action Pathway

Fosinopril Metabolism Pathway

Fosinopril ACE Inhibitor Action Pathway

Fosinopril Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Prolyl endopeptidase	P48147	Humans	Predicted (SEA)	79.5619
Click to view 3D structure	Breast cancer type 1 susceptibility protein	P38398	Humans	Predicted (SEA)	126.427
Click to view 3D structure	Prolyl endopeptidase	O70196	Rattus norvegicus	Predicted (SEA)	38.224
Click to view 3D structure	Prolyl endopeptidase	Q9XTA2	Bos taurus	Predicted (SEA)	62.9022
Click to view 3D structure	Mitofusin-2	O95140	Humans	Predicted (SEA)	45.3861
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	1704.43
Click to view 3D structure	Neprilysin	P08049	Oryctolagus cuniculus	Predicted (SEA)	301.977
Click to view 3D structure	Serine protease 1	P00760	Bos taurus	Predicted (SEA)	409.876
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	2883.54
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	1571.78
Click to view 3D structure	Glutamyl aminopeptidase	P16406	Mus musculus	Predicted (SEA)	58.3869
Click to view 3D structure	Renin	P00797	Humans	Predicted (SEA)	353.513
Click to view 3D structure	72 kDa type IV collagenase	P08253	Humans	Predicted (SEA)	1647.21
Click to view 3D structure	Angiotensin-converting enzyme	P12821	Humans	Predicted (SEA)	44.6855
Click to view 3D structure	Angiotensin-converting enzyme	P12822	Oryctolagus cuniculus	Predicted (SEA)	33.8644
Click to view 3D structure	Angiotensin-converting enzyme	P47820	Rattus norvegicus	Predicted (SEA)	35.11
Click to view 3D structure	FK506 binding protein 12	Q8QGU2	Gallus gallus	Predicted (SEA)	4.12601
Click to view 3D structure	Prolyl endopeptidase	P23687	Sus scrofa	Predicted (SEA)	32.4631
Click to view 3D structure	Peptidyl-prolyl cis-trans isomerase FKBP1A	Q62658	Rattus norvegicus	Predicted (SEA)	9.73115
Click to view 3D structure	GIM-1 protein	Q704V1	Pseudomonas aeruginosa	Predicted (SEA)	14.48
Click to view 3D structure	Inositol monophosphatase 1	P20456	Bos taurus	Predicted (SEA)	4.7488
Click to view 3D structure	Prolyl endopeptidase	Q9QUR6	Mus musculus	Predicted (SEA)	30.439
Click to view 3D structure	Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	Humans	Predicted (SEA)	14.0129
Click to view 3D structure	Neprilysin	P07861	Rattus norvegicus	Predicted (SEA)	218.756
Click to view 3D structure	Angiotensin-converting enzyme 2	Q5EGZ1	Rattus norvegicus	Predicted (SEA)	36.7448