(4,5-13C2)-1,3-thiazol-5-yl(13C)methyl N-[(2S,3S,5S)-3-hydroxy-5-[(2S)-3-methyl-2-{[methyl({[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl})carbamoyl]amino}butanamido]-1,6-diphenylhexan-2-yl]carbamate

• ChemBase ID: 177574
• Molecular Formular: C37H48N6O5S2
• Molecular Mass: 723.92218451
• Monoisotopic Mass: 723.32282518
• SMILES: [13CH2](OC(=O)N[C@H]([C@H](C[C@@H](NC(=O)[C@@H](NC(=O)N(C)Cc1nc(sc1)C(C)C)C(C)C)Cc1ccccc1)O)Cc1ccccc1)[13c]1[13cH]ncs1
• Canonical SMILES: O=C(N[C@H]([C@H](C[C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=O)N(Cc1csc(n1)C(C)C)C)O)Cc1ccccc1)O[13CH2][13c]1[13cH]ncs1
• InChI: InChI=1S/C37H48N6O5S2/c1-24(2)33(42-36(46)43(5)20-29-22-49-35(40-29)25(3)4)34(45)39-28(16-26-12-8-6-9-13-26)18-32(44)31(17-27-14-10-7-11-15-27)41-37(47)48-21-30-19-38-23-50-30/h6-15,19,22-25,28,31-33,44H,16-18,20-21H2,1-5H3,(H,39,45)(H,41,47)(H,42,46)/t28-,31-,32-,33-/m0/s1/i19+1,21+1,30+1
• InChIKey: NCDNCNXCDXHOMX-MZPZWQAXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4,5-^1^3C₂)-1,3-thiazol-5-yl(^1^3C)methyl N-[(2S,3S,5S)-3-hydroxy-5-[(2S)-3-methyl-2-{[methyl({[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl})carbamoyl]amino}butanamido]-1,6-diphenylhexan-2-yl]carbamate
• IUPAC Traditional name: (4,5-^1^3C₂)-1,3-thiazol-5-yl(^1^3C)methyl N-[(2S,3S,5S)-3-hydroxy-5-[(2S)-2-({[(2-isopropyl-1,3-thiazol-4-yl)methyl](methyl)carbamoyl}amino)-3-methylbutanamido]-1,6-diphenylhexan-2-yl]carbamate
• Synonyms: (3S,4S,6S,9S)-4-Hydroxy-12-methyl-9-(1-methylethyl)-13-[2-(1-methylethyl)-4-thiazolyl]-8,11-dioxo-3,6-bis(phenylmethyl)-2,7,10,12-tetraazatridecanoic Acid 5-Thiazolylmethyl-13C3 Ester; Ritonavir-13C3; A 84538-13C3; ABT 538-13C3; Norvir-13C3

Database IDs

• PubChem SID: 164233484
• PubChem CID: 45040376

CALCULATED PROPERTIES

• Acid pKa: 13.678454
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 5.221135
• LogD (pH = 7.4): 5.2217736
• Log P: 5.221782
• Molar Refractivity: 194.5924 cm^3
• Polarizability: 75.68044 Å^3
• Polar Surface Area: 145.78 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: White Solid
• Melting Point: 60-62°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - R535003

A stable labelled selective HIV protease inhibitor Ritonavir (R535000).

REFERENCES

• Daluge, S., et al.: Antimicrob. Agents Chemother., 38, 1590 (1994)
• Ammaranond, P., et al.: J. Clin. Virol., 26, 153(1994)
• Harrigan, P., et al.: J. Infect. Dis., 191, 339 (1994)
• Miller, J., et al.: Bioorg. Med. Chem. Lett., 16, 1788 (2006)