(2S)-2-{[(2S,6R)-4-(carboxymethyl)-5-oxo-2-(thiophen-2-yl)-1,4-thiazepan-6-yl]amino}-4-phenylbutanoic acid

• ChemBase ID: 178135
• Molecular Formular: C21H24N2O5S2
• Molecular Mass: 448.55566
• Monoisotopic Mass: 448.11266388
• SMILES: c1cccc(c1)CC[C@@H](C(=O)O)N[C@@H]1C(=O)N(C[C@H](SC1)c1cccs1)CC(=O)O
• Canonical SMILES: OC(=O)CN1C[C@H](SC[C@@H](C1=O)N[C@H](C(=O)O)CCc1ccccc1)c1cccs1
• InChI: InChI=1S/C21H24N2O5S2/c24-19(25)12-23-11-18(17-7-4-10-29-17)30-13-16(20(23)26)22-15(21(27)28)9-8-14-5-2-1-3-6-14/h1-7,10,15-16,18,22H,8-9,11-13H2,(H,24,25)(H,27,28)/t15-,16-,18-/m0/s1
• InChIKey: KZVWEOXAPZXAFB-BQFCYCMXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S,6R)-4-(carboxymethyl)-5-oxo-2-(thiophen-2-yl)-1,4-thiazepan-6-yl]amino}-4-phenylbutanoic acid
• IUPAC Traditional name: temocaprilat
• Synonyms: (2S,6R)-6-[[(1S)-1-Carboxy-3-phenylpropyl]amino]tetrahydro-5-oxo-2-(2-thienyl)-1,4- thiazepine-4(5H)-acetic Acid; RS-5139; Temocapril Diacid; Temocaprilate; Temocaprilat

Database IDs

• CAS Number: 110221-53-9
• PubChem SID: 164234045
• PubChem CID: 443151

CALCULATED PROPERTIES

• Polarizability: 44.996315 Å^3
• Polar Surface Area: 106.94 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true
• Acid pKa: 3.4293299
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.937514
• LogD (pH = 7.4): -2.8066957
• Log P: 0.13352434
• Molar Refractivity: 114.5822 cm^3

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White to Off-White Solid
• Melting Point: >230°C (dec)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T017305

Antihypertensive.

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)