(2S,3S)-5-(2-aminoethyl)-2-(4-hydroxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate

• ChemBase ID: 178986
• Molecular Formular: C19H20N2O4S
• Molecular Mass: 372.4381
• Monoisotopic Mass: 372.11437813
• SMILES: c1(ccc(cc1)[C@H]1[C@H](C(=O)N(c2c(S1)cccc2)CCN)OC(=O)C)O
• Canonical SMILES: NCCN1C(=O)[C@H](OC(=O)C)[C@@H](Sc2c1cccc2)c1ccc(cc1)O
• InChI: InChI=1S/C19H20N2O4S/c1-12(22)25-17-18(13-6-8-14(23)9-7-13)26-16-5-3-2-4-15(16)21(11-10-20)19(17)24/h2-9,17-18,23H,10-11,20H2,1H3/t17-,18+/m1/s1
• InChIKey: HLUHIUIPTZZNFN-MSOLQXFVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-5-(2-aminoethyl)-2-(4-hydroxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate
• IUPAC Traditional name: (2S,3S)-5-(2-aminoethyl)-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl acetate
• Synonyms: (2S,3S)-3-(Acetyloxy)-5-(2-aminoethyl)-2,3-dihydro-2-(4-hydroxyphenyl)-1,5-benzothiazepin-4(5H)-one; (2S-cis)-3-(Acetyloxy)-5-(2-aminoethyl)-2,3-dihydro-2-(4-hydroxyphenyl)-1,5-benzothiazepin-4(5H)-one; N,N,O-Tridesmethyl Diltiazem

Database IDs

• CAS Number: 159734-23-3
• PubChem SID: 164234896
• PubChem CID: 71752721

CALCULATED PROPERTIES

• Acid pKa: 9.608366
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.134414
• LogD (pH = 7.4): 0.18798743
• Log P: 1.3617759
• Molar Refractivity: 99.8147 cm^3
• Polarizability: 39.2302 Å^3
• Polar Surface Area: 92.86 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T775500

A metabolite of Diltiazem (D460620).

REFERENCES

• Gendron, F., et al.: Biochem. Pharmacol., 60, 1959 (2000)
• Molden, E., et al.: J. Pharm. Biomed. Anal., 33, 275 (2000)
• Ma, J., et al.: Mol. Pharmacol., 72, 380 (2000)