(2R)-2-[(3S,5aS,9aR,10aS)-3-methyl-1,4-dioxo-dodecahydropiperazino[1,2-a]indol-2-yl]-4-phenylbutanoic acid

• ChemBase ID: 178806
• Molecular Formular: C22H28N2O4
• Molecular Mass: 384.46872
• Monoisotopic Mass: 384.20490739
• SMILES: N12[C@@H]3[C@@H](C[C@H]1C(=O)N([C@H](C2=O)C)[C@H](CCc1ccccc1)C(=O)O)CCCC3
• Canonical SMILES: OC(=O)[C@H](N1[C@@H](C)C(=O)N2[C@H](C1=O)C[C@@H]1[C@@H]2CCCC1)CCc1ccccc1
• InChI: InChI=1S/C22H28N2O4/c1-14-20(25)24-17-10-6-5-9-16(17)13-19(24)21(26)23(14)18(22(27)28)12-11-15-7-3-2-4-8-15/h2-4,7-8,14,16-19H,5-6,9-13H2,1H3,(H,27,28)/t14-,16+,17-,18+,19-/m0/s1
• InChIKey: KSVWPQFHTVGGLP-YYTXDEJISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(3S,5aS,9aR,10aS)-3-methyl-1,4-dioxo-dodecahydropiperazino[1,2-a]indol-2-yl]-4-phenylbutanoic acid
• IUPAC Traditional name: (2R)-2-[(3S,5aS,9aR,10aS)-3-methyl-1,4-dioxo-octahydro-3H-piperazino[1,2-a]indol-2-yl]-4-phenylbutanoic acid
• Synonyms: [3S-[2(R*),3α,5aβ,9aα,10aβ]]-Decahydro-3-methyl-1,4-dioxo-α-(2-phenylethyl)pyrazino[1,2-a]indole-2(1H)-acetic Acid; RU 51057; Trandolaprilat Diketopiperazine

Database IDs

• CAS Number: 149756-14-9
• PubChem SID: 164234716
• PubChem CID: 71752648

CALCULATED PROPERTIES

• Acid pKa: 4.04415
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.3887165
• LogD (pH = 7.4): -0.27734223
• Log P: 2.8558593
• Molar Refractivity: 103.1923 cm^3
• Polarizability: 40.557606 Å^3
• Polar Surface Area: 77.92 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T713535

Trandolaprilat Diketopiperazine is a metabolite of the antihypertensive Trandolapril (Ru44570) (T713500), an angiotensin-converting enzyme inhibitor.