Showing Compound Lisinopril (FDB022753)

Record Information

Version

1.0

Creation date

2011-09-21 00:19:05 UTC

Update date

2018-05-28 18:33:55 UTC

Primary ID

FDB022753

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Lisinopril

Description

One of the Angiotensin-converting enzyme inhibitors (ACE inhibitors), orally active, that has been used in the treatment of hypertension and congestive heart failure. -- Pubchem; Lisinopril is a drug of the angiotensin converting enzyme (ACE) inhibitor class that is primarily used in treatment of hypertension, congestive heart failure and heart attacks. Historically, lisinopril was the third ACE inhibitor, after captopril and enalapril that was introduced into therapy in early 1990s . Lisinopril has a number of properties that distinguish it from other ACE inhibitors: it is hydrophilic, has long half life and tissue penetration and is not metabolized by the liver. -- Wikipedia; Lisinopril is solely excreted in urine in the unchanged form. Elimination of the drug depends on glomerular filtration and tubular excretion. Rate of lisinopril elimination decreases with old age and kidney or heart failure. There is a relation between creatinine and lisinopril clearance. With prolonged therapy dose reduction can be necessary to avoid accumulation. -- Wikipedia [HMDB]

CAS Number

83915-83-7

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(S)-1-(N(2)-(1-Carboxy-3-phenylpropyl)-L-lysyl)-L-proline	ChEBI
[N2-[(S)-1-CARBOXY-3-phenylpropyl]-L-lysyl-L-proline	ChEBI
Lisinopril anhydrous	ChEBI
Zestril	Kegg
Acerbon	HMDB
Acercomp	HMDB
Alapril	HMDB
Carace	HMDB
Cipral	HMDB
Cipril	HMDB
Coric	HMDB
Inhibril	HMDB
Inopril	HMDB
Linopril	HMDB
Linvas	HMDB
Lipril	HMDB
Lisinal	HMDB
Lisinoprilum	HMDB
Lisipril	HMDB
Lisoril	HMDB
Lispril	HMDB
Loril	HMDB
LPR	HMDB
Lysinopril	HMDB
Noperten	HMDB
Novatec	HMDB
Presiten	HMDB
Prinil	HMDB
Prinivil	HMDB
Sinopril	HMDB
Sinopryl	HMDB
Tensopril	HMDB
Tensyn	HMDB
Tersif	HMDB
Vivatec	HMDB
Lisinopril maleate (1:1)	HMDB
Lisinopril sulfate (1:2)	HMDB
Lisinopril	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-3.1	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.96 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	107.37 m³·mol⁻¹	ChemAxon
Polarizability	43.64 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C21H31N3O5

IUPAC name

(2S)-1-[(2S)-6-amino-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid

InChI Identifier

InChI=1S/C21H31N3O5/c22-13-5-4-9-16(19(25)24-14-6-10-18(24)21(28)29)23-17(20(26)27)12-11-15-7-2-1-3-8-15/h1-3,7-8,16-18,23H,4-6,9-14,22H2,(H,26,27)(H,28,29)/t16-,17-,18-/m0/s1

InChI Key

RLAWWYSOJDYHDC-BZSNNMDCSA-N

Isomeric SMILES

NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1CCC[C@H]1C(O)=O

Average Molecular Weight

405.4879

Monoisotopic Molecular Weight

405.226371117

Classification

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
N-acyl-alpha-amino acid
Proline or derivatives
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
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
Organoheterocyclic compound
Secondary amine
Azacycle
Carboxylic acid
Secondary aliphatic amine
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Organooxygen compound
Primary amine
Amine
Organic oxygen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:43755 )

Ontology

Disposition

Biological location:

Organ and components:

Tissue and substructures:

Skeletal muscle

Role

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Lisinopril, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9344000000-3673a7191e97a0ee02e0	Spectrum
Predicted GC-MS	Lisinopril, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0f6x-9201340000-bc9644b3a3a4109f3722	Spectrum
Predicted GC-MS	Lisinopril, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0ik9-0900500000-85d2bfa23ac02fce017d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-03di-0900000000-b4cd463dbaeec149b805	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-c2a4ab9f5fb48e5480bf	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4r-0194100000-d9a47a283478b88bb101	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9040000000-8d6d4ae6ba18da11e336	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-77e20f7eb799eea58ab0	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-01q0-0940000000-116994867a4e2c649c00	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-01q0-0940000000-116994867a4e2c649c00	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9120000000-fd2acaa1eae37a6f7ba6	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-2010900000-67e85126826eedd63b6c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-053r-9052300000-d651e557fe1ae7eac452	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0w29-0119600000-219bea00e0a247bc0888	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-2429100000-404746794cb47e7eb6fc	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-3920000000-b1093c7b1913ec8ec8d0	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0002900000-ce436e39fbead59af3f2	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ik9-3933500000-a236ac37e133779ee0ac	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03dj-8910000000-db165b4504f7321c51e0	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06ri-0229300000-236b576cdfc8112530c7	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03xu-4497000000-ad2ca7e02728a51b0051	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9760000000-517501fe175444669d72	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0002900000-a76c25515295bb79175b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0901-2395300000-cc32f663c74e5f0f3306	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9110000000-ccd25ccd5c2ff94948b4	2021-09-24	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		Spectrum