(2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-4-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamoyl}butyl]-N-tert-butylpiperazine-2-carboxamide

• ChemBase ID: 166676
• Molecular Formular: C30H42N4O4
• Molecular Mass: 522.67888
• Monoisotopic Mass: 522.32060584
• SMILES: N1C[C@H](N(CC1)C[C@H](C[C@H](C(=O)N[C@H]1c2c(C[C@H]1O)cccc2)Cc1ccccc1)O)C(=O)NC(C)(C)C
• Canonical SMILES: O[C@@H](C[C@H](C(=O)N[C@@H]1[C@H](O)Cc2c1cccc2)Cc1ccccc1)CN1CCNC[C@H]1C(=O)NC(C)(C)C
• InChI: InChI=1S/C30H42N4O4/c1-30(2,3)33-29(38)25-18-31-13-14-34(25)19-23(35)16-22(15-20-9-5-4-6-10-20)28(37)32-27-24-12-8-7-11-21(24)17-26(27)36/h4-12,22-23,25-27,31,35-36H,13-19H2,1-3H3,(H,32,37)(H,33,38)/t22-,23+,25+,26-,27+/m1/s1
• InChIKey: MKMGKCALCCOODL-XXEBQWMLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-4-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamoyl}butyl]-N-tert-butylpiperazine-2-carboxamide
• IUPAC Traditional name: (2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-4-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamoyl}butyl]-N-tert-butylpiperazine-2-carboxamide
• Synonyms: 2,3,5-Trideoxy-N-[(1S,2R)-2,3-dihydro-2-hydroxy-1H-inden-1-yl]-5-[(2S)-2-[[(1,1-dimethylethyl)amino]carbonyl]-1-piperazinyl]-2-(phenylmethyl)-D-erythro-pentonamide; Des-3-pyridylmethyl Indinavir

Database IDs

• CAS Number: 150323-38-9
• PubChem SID: 162260809
• PubChem CID: 5479517

CALCULATED PROPERTIES

• Acid pKa: 13.251525
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -0.8771674
• LogD (pH = 7.4): 0.8069392
• Log P: 1.9200822
• Molar Refractivity: 148.1437 cm^3
• Polarizability: 58.31649 Å^3
• Polar Surface Area: 113.93 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol

DETAILS

Toronto Research Chemicals - D297400

An Intermediate in the preparation of Indinavir and also a metabolite of Indinavir.

REFERENCES

• Askin, D., etal.: Tetrahedron Lett., 35, 673 (1994)
• Lin, J.H., et al.: Drug Metab. Dispos. 24, 1111 (1996).