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

• ChemBase ID: 44456
• Molecular Formular: C21H35N3O7
• Molecular Mass: 441.5185
• Monoisotopic Mass: 441.24750048
• SMILES: N1(C(=O)[C@@H](N[C@H](C(=O)O)CCc2ccccc2)CCCCN)[C@H](C(=O)O)CCC1.O.O
• Canonical SMILES: NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N[C@H](C(=O)O)CCc1ccccc1.O.O
• InChI: InChI=1S/C21H31N3O5.2H2O/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);2*1H2/t16-,17-,18-;;/m0../s1
• InChIKey: CZRQXSDBMCMPNJ-ZUIPZQNBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-6-amino-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid dihydrate
• IUPAC Traditional name: lisinopril dihydrate
• Synonyms: Lisinopril; (S)-1-[N2-(1-carboxy-3-phenylpropyl)-lysyl-proline dihydrate; MK-521; Lisinopril

Database IDs

• CAS Number: 83915-83-7
• EC Number: 278-488-1
• MDL Number: MFCD01698825
• PubChem SID: 162049219
• PubChem CID: 5362118

CALCULATED PROPERTIES

• Acid pKa: 3.1725657
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -3.1054642
• LogD (pH = 7.4): -3.1834292
• Log P: -3.1026032
• Molar Refractivity: 107.3691 cm^3
• Polarizability: 42.540714 Å^3
• Polar Surface Area: 132.96 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ~6.5 mg/mL (with heating and sonicating); H2O: ≥10 mg/mL
• Apperance: white solid

Safety Information

• Storage Warning: IRRITANT
• RTECS: TW3589990
• German water hazard class: 2; 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ACE(1636)

Product Information

• Purity: >95%; ≥98% (HPLC)
• Grade: certified reference material
• Packaging: pkg of 1 g
• Pharmacopeia Traceability: traceable to BP 695; traceable to PhEur L0702000; traceable to USP 1368609
• Empirical Formula (Hill Notation): C21H31O5N3 · 2H2O

DETAILS

Sigma Aldrich - L6292

Biochem/physiol Actions
Angiotensin converting enzyme (ACE) inhibitor.

Sigma Aldrich - PHR1143

Biochem/physiol Actions
Angiotensin converting enzyme (ACE) inhibitor.
General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.