ethyl (2S)-2-[(3S,11aS)-8,9-dimethoxy-3-methyl-1,4-dioxo-1H,2H,3H,4H,6H,11H,11aH-piperazino[1,2-b]isoquinolin-2-yl]-4-phenylbutanoate

• ChemBase ID: 174686
• Molecular Formular: C27H32N2O6
• Molecular Mass: 480.55278
• Monoisotopic Mass: 480.22603675
• SMILES: c1(c(cc2c(c1)C[C@@H]1N(C2)C(=O)[C@@H](N(C1=O)[C@@H](CCc1ccccc1)C(=O)OCC)C)OC)OC
• Canonical SMILES: CCOC(=O)[C@@H](N1[C@@H](C)C(=O)N2[C@H](C1=O)Cc1c(C2)cc(c(c1)OC)OC)CCc1ccccc1
• InChI: InChI=1S/C27H32N2O6/c1-5-35-27(32)21(12-11-18-9-7-6-8-10-18)29-17(2)25(30)28-16-20-15-24(34-4)23(33-3)14-19(20)13-22(28)26(29)31/h6-10,14-15,17,21-22H,5,11-13,16H2,1-4H3/t17-,21-,22-/m0/s1
• InChIKey: UYPPDNXTLSUNRF-HSQYWUDLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2S)-2-[(3S,11aS)-8,9-dimethoxy-3-methyl-1,4-dioxo-1H,2H,3H,4H,6H,11H,11aH-piperazino[1,2-b]isoquinolin-2-yl]-4-phenylbutanoate
• IUPAC Traditional name: ethyl (2S)-2-[(3S,11aS)-8,9-dimethoxy-3-methyl-1,4-dioxo-3H,6H,11H,11aH-piperazino[1,2-b]isoquinolin-2-yl]-4-phenylbutanoate
• Synonyms: (αS,3S,11aS)-1,3,4,6,11,11a-Hexahydro-8,9-dimethoxy-3-methyl-1,4-dioxo-α-(2-phenylethyl)-2H-pyrazino[1,2-b]isoquinoline-2-acetic Acid Ethyl Ester; [3S-[2(R*),3α,11aβ]]-1,3,4,6,11,11a-Hexahydro-8,9-dimethoxy-3-methyl-1,4-dioxo-α-(2-phenylethyl)-2H-pyrazino[1,2-b]isoquinoline-2-acetic Acid Ethyl Ester; PD 114009; Moexipril Diketopiperazine

Database IDs

• CAS Number: 103733-51-3
• PubChem SID: 164230596
• PubChem CID: 71750760

CALCULATED PROPERTIES

• Acid pKa: 18.696732
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 3.11687
• LogD (pH = 7.4): 3.11687
• Log P: 3.11687
• Molar Refractivity: 129.8044 cm^3
• Polarizability: 50.64177 Å^3
• Polar Surface Area: 85.38 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 74-77°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M485340

An impurity of Moexipril (M485350). The degradation kinetics of Moexipril produced by organic solvents.

REFERENCES

• Gu, L., et al.: Int. J. Pharmaceutics., 60, 99 (1990)
• Strickley, R.G., et al.: Pharmaceut. Res., 6, 971 (1990)