2-[(2S,6R)-6-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-5-oxo-2-(thiophen-2-yl)-1,4-thiazepan-4-yl]acetic acid hydrochloride

• ChemBase ID: 178133
• Molecular Formular: C23H29ClN2O5S2
• Molecular Mass: 513.06976
• Monoisotopic Mass: 512.12064172
• SMILES: c1cccc(c1)CC[C@@H](C(=O)OCC)N[C@@H]1C(=O)N(C[C@H](SC1)c1cccs1)CC(=O)O.Cl
• Canonical SMILES: CCOC(=O)[C@@H](N[C@H]1CS[C@@H](CN(C1=O)CC(=O)O)c1cccs1)CCc1ccccc1.Cl
• InChI: InChI=1S/C23H28N2O5S2.ClH/c1-2-30-23(29)17(11-10-16-7-4-3-5-8-16)24-18-15-32-20(19-9-6-12-31-19)13-25(22(18)28)14-21(26)27;/h3-9,12,17-18,20,24H,2,10-11,13-15H2,1H3,(H,26,27);1H/t17-,18-,20-;/m0./s1
• InChIKey: XDDQNOKKZKHBIX-ASBZXGSUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2S,6R)-6-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-5-oxo-2-(thiophen-2-yl)-1,4-thiazepan-4-yl]acetic acid hydrochloride
• IUPAC Traditional name: [(2S,6R)-6-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-5-oxo-2-(thiophen-2-yl)-1,4-thiazepan-4-yl]acetic acid hydrochloride
• Synonyms: (2S,6R)-6-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]tetrahydro-5-oxo-2-(2-thienyl)-1,4-thiazepine-4(5H)-acetic Acid Hydrochloride; CS-622; Acecol; Temocapril Hydrochloride; Temocapril HCl

Database IDs

• CAS Number: 110221-44-8
• PubChem SID: 164234043
• PubChem CID: 443873

CALCULATED PROPERTIES

• Acid pKa: 3.87721
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.7803457
• LogD (pH = 7.4): 0.22307292
• Log P: 2.042777
• Molar Refractivity: 124.0999 cm^3
• Polarizability: 48.907978 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Methanol,
• Apperance: White To Off-White Solid
• Melting Point: 188-191°C (dec)

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Target: RAAS

Product Information

• Salt Data: HCl

DETAILS

Toronto Research Chemicals - T017301

Angiotensin-converting enzyme (ACE) inhibitor. Hydrolyzed in vivo to the active diacid metabolite.

REFERENCES

• Qizumi, K., et al.: Jpn. J. Pharmacol., 48, 349 (1988)
• Arita, M., et al.: Clin. Exp. Pharmacol. Physiol., 21, 195 (1988)
• Tokunaga, S., et al.: Drug Invest., 7, 161 (1994)