(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoic acid

• ChemBase ID: 71001
• Molecular Formular: C15H21NO4
• Molecular Mass: 279.33154
• Monoisotopic Mass: 279.14705816
• SMILES: C(=O)([C@H](C)N[C@H](C(=O)OCC)CCc1ccccc1)O
• Canonical SMILES: CCOC(=O)[C@@H](N[C@H](C(=O)O)C)CCc1ccccc1
• InChI: InChI=1S/C15H21NO4/c1-3-20-15(19)13(16-11(2)14(17)18)10-9-12-7-5-4-6-8-12/h4-8,11,13,16H,3,9-10H2,1-2H3,(H,17,18)/t11-,13-/m0/s1
• InChIKey: CEIWXEQZZZHLDM-AAEUAGOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoic acid
• IUPAC Traditional name: (2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoic acid
• Synonyms: (S)-2-(((S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoic acid; N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine; (αS)-α-[[(1S)-1-carboxyethyl]amino]benzenebutanoic Acid; N-[(S)-1-Ethoxycarbonyl-3-phenylpropyl]-L-alanine; (+)-N-[1-(S)-Ethoxycarbonxyl-3-phenylpropyl]-L-alanine; N-[(S)-(+)-1-(乙氧羰基)-3-苯丙基]-L-丙氨酸

Database IDs

• CAS Number: 82717-96-2
• MDL Number: MFCD00209976
• PubChem SID: 162036709; 24870822
• PubChem CID: 5702571

CALCULATED PROPERTIES

• Polarizability: 29.715288 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true
• Acid pKa: 3.2602518
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.97740525
• LogD (pH = 7.4): -0.46684456
• Log P: 1.1734784
• Molar Refractivity: 74.5881 cm^3

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 150-152 °C(lit.); 153-154°C
• Optical Rotation: [α]20/D +28°, c = 1 in methanol

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false

Product Information

• Purity: 95+%; 98%
• Linear Formula: C6H5CH2CH2CH(CO2C2H5)NHCH(CH3)CO2H

DETAILS

Sigma Aldrich - 472735

Packaging
5 g in glass bottle

Toronto Research Chemicals - E891586

Moexipril intermediate; the main metabolite of Imidapril.

REFERENCES

• Yamada, Y., et al.: Arzneim.-Forsch., 42(4)
• 490 (4)