Lisinopril

Athanor · official

C₂₁H₃₁N₃O₅ · 405.5 g/mol

IUPAC name: (2S)-1-[(2S)-6-amino-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid

Also called Zestril, Prinivil, ACE inhibitor

Drugs Amino acids

Open in Athanor

Drawn from its SMILES with RDKit

DangerCauses skin irritation · Causes serious eye irritation · May damage fertility or the unborn child · May damage the unborn child · Suspected of damaging fertility or the unborn child · May cause harm to breast-fed children · May causes damage to organs through prolonged or repeated exposure

Names and identifiers

IUPAC name: (2S)-1-[(2S)-6-amino-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid
Synonyms: Zestril, Prinivil, ACE inhibitor
+ 36 more
Lisinopril anhydrous, Lysinopril, Carace, Novatec, Lisinoprilum, Lisinoprilum [Latin], Qbrelis, 7Q3P4BS2FD, MK-521, [N2-[(S)-1-CARBOXY-3-PHENYLPROPYL]-L-LYSYL-L-PROLINE, N-(1(S)-Carboxy-3-phenylpropyl)-L-lysyl-L-proline, N2-((S)-1-Carboxy-3-phenylpropyl)-L-lysyl-L-proline, (2S)-1-[(2S)-6-amino-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid, L-Proline, N2-((1S)-1-carboxy-3-phenylpropyl)-L-lysyl-, DTXSID6040537, (S)-1-(N(2)-(1-carboxy-3-phenylpropyl)-L-lysyl)-L-proline, CHEBI:43755, Lisinoprilum (Latin), L-Proline, 1-(N2-(1-carboxy-3-phenylpropyl)-L-lysyl)-, (S)-, NSC-751176, NSC-758151, (2S)-1-[(2S)-6-amino-2-[[(2S)-1-hydroxy-1-oxo-4-phenylbutan-2-yl]amino]hexanoyl]pyrrolidine-2-carboxylic acid, L-PROLINE, 1-(N(SUP 2)-(1-CARBOXY-3-PHENYLPROPYL)-L-LYSYL)-, 1-(N(SUP 2)-((S)-1-CARBOXY-3-PHENYLPROPYL)-L-LYSYL)-L-PROLINE, (2S)-1-[(2S)-6-amino-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid, (N2-((S)-1-carboxy-3-phenylpropyl)-L-lysyl-L-proline, L-Proline, N2-[(1S)-1-carboxy-3-phenylpropyl]-L-lysyl-, Lisinoril, Lisopress, (2S)-1-((2S)-6-amino-2-(((1S)-1-carboxy-3-phenylpropyl)amino)hexanoyl)pyrrolidine-2-carboxylic acid, (2S)-1-((2S)-6-amino-2-(((2S)-1-hydroxy-1-oxo-4-phenylbutan-2-yl)amino)hexanoyl)pyrrolidine-2-carboxylic acid, L-Proline, 1-(N2-(1-carboxy-3-phenylpropyl)-L-lysyl)-, dihydrate, (S)-, RefChem:5952, L-Proline, 1-(N(sup 2)-(1-carboxy-3-phenylpropyl)-L-lysyl)-, dihydrate, (S)-, DTXCID4020537, C09AA03
Molecular formula: C₂₁H₃₁N₃O₅
Empirical formula: C₂₁H₃₁N₃O₅
Molecular weight: 405.5 g/mol
Exact mass: 405.22637
CAS number: 83915-83-7
PubChem CID: 5362119
Canonical SMILES: C1CC(N(C1)C(=O)C(CCCCN)NC(CCC2=CC=CC=C2)C(=O)O)C(=O)O
Isomeric SMILES: C1C[C@H](N(C1)C(=O)[C@H](CCCCN)N[C@@H](CCC2=CC=CC=C2)C(=O)O)C(=O)O
InChI: 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
InChIKey: RLAWWYSOJDYHDC-BZSNNMDCSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Physical properties

log P: log Kow = -1.22[1]

Each value as its source reports it, with the source's number after it (listed under References). Where several sources report a property, the row shows the value most of them agree on, the rule the app uses; open the values to see every one.

Calculated

Heavy atoms: 29
Rings: 2
Aromatic rings: 1
Fraction sp³ carbons (Fsp3): 0.57
H-bond donors: 4
H-bond acceptors: 5 computed here · PubChem 7
Rotatable bonds: 12
TPSA (Å²): 133
Formal charge: 0
XLogP3: -2.9 PubChem
Complexity: 550 PubChem
Stereocenters: 3 definedCIP: C6: S · C8: S · C26: S
Double-bond geometry: None specified
Point group: C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

C62.20%
H7.71%
N10.36%
O19.73%

Isotope pattern

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P: 1.24 Crippen (Wildman and Crippen 1999)
log S (water solubility): -2.49 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 3.17 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 405.5
log P ≤ 5 (Crippen): 1.24
H-bond donors ≤ 5: 4
H-bond acceptors ≤ 10: 5

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Danger

Most widely reported: 7 company reports to ECHA. Source [2].

Harmful or irritant
Health hazard

H315Causes skin irritation (28.6% of reports)
H319Causes serious eye irritation (71.4% of reports)
H360May damage fertility or the unborn child (42.9% of reports)
H360DMay damage the unborn child (14.3% of reports)
H361Suspected of damaging fertility or the unborn child (28.6% of reports)
H362May cause harm to breast-fed children (28.6% of reports)
H373May causes damage to organs through prolonged or repeated exposure (42.9% of reports)

Precautionary statements: P203, P260, P263, P264, P264+P265, P270, P280, P302+P352, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P405, P501

View all classifications (3)

[2] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for 14.3% (1 of 7) of reports.
[2] European Chemicals Agency (ECHA) · 7 reports · DangerH315, H319, H360, H360D, H361, H362, H373
[2] European Chemicals Agency (ECHA) · DangerH360

Storage

Keep container tightly closed in a dry and well-ventilated place. Storage class (TRGS 510): Non Combustible Solids.[1]
Store at controlled room temperature, 15-30 °C (59-86 °F), and protect from moisture.[1]

Incompatibilities

Incompatible materials: Strong oxidizing agents.[1]

Safety data sheets on the supplier’s page: AbMole Bioscience, Alfa Chemistry, Protheragen.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

[1]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
[2]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
[3]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
[4]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
[5]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
[6]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
[7]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
·Literature on PubChem

Data last updated 2026-10-14.