(3S)-2-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrate

• ChemBase ID: 155036
• Molecular Formular: C23H28N2O6
• Molecular Mass: 428.47822
• Monoisotopic Mass: 428.19473663
• SMILES: C[C@@H](C(=O)N1Cc2ccccc2C[C@H]1C(=O)O)N[C@@H](CCc1ccccc1)C(=O)O.O
• Canonical SMILES: OC(=O)[C@@H](N[C@H](C(=O)N1Cc2ccccc2C[C@H]1C(=O)O)C)CCc1ccccc1.O
• InChI: InChI=1S/C23H26N2O5.H2O/c1-15(24-19(22(27)28)12-11-16-7-3-2-4-8-16)21(26)25-14-18-10-6-5-9-17(18)13-20(25)23(29)30;/h2-10,15,19-20,24H,11-14H2,1H3,(H,27,28)(H,29,30);1H2/t15-,19-,20-;/m0./s1
• InChIKey: OFYSYEOWQQCPEU-ZAFWUOJLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-2-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrate
• IUPAC Traditional name: quinaprilat hydrate
• Synonyms: Quinaprilat hydrate; (3S)-2-[(2S)-2-[[(1S)-1-Carboxy-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid hydrate

Database IDs

• CAS Number: 82768-85-2(anhydrous)
• MDL Number: MFCD08060097
• PubChem SID: 162249174
• PubChem CID: 25030442

CALCULATED PROPERTIES

• Acid pKa: 3.066926
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.9201111
• LogD (pH = 7.4): -2.675691
• Log P: 0.29924572
• Molar Refractivity: 110.4381 cm^3
• Polarizability: 43.2194 Å^3
• Polar Surface Area: 106.94 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥23 mg/mL
• Apperance: white to tan powder
• Optical Rotation: [α]/D +16 to +23 ( C=1, MeOH)

Safety Information

• European Hazard Symbols: Nature polluting (N); Toxic (T)
• German water hazard class: 3
• Risk Statements: 25-50
• Safety Statements: 45-61
• GHS Pictograms: GHS06; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H400
• GHS Precautionary statements: P273-P301 + P310
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C23H26N2O5 · xH2O

DETAILS

Sigma Aldrich - Q0264

Biochem/physiol Actions
Quinaprilat is the active metabolite of Quinapril. It is an angiotensin converting enzyme (ACE) inhibitor, an antihypertensive used in treatment of congestive heart failure. Quinaprilat has high affinity to tissue ACE, and has been shown to improve impaired flow-dependent (endothelium-mediated) dilation (FDD) in patients with chronic heart failure compared to other ACE inhibitors with low affinity for tissue ACE.