tert-butyl (2S)-2-[(2S)-2-{[(2S)-6-{[(benzyloxy)carbonyl]amino}-1-methoxy-1-oxohexan-2-yl]carbamoyl}-2,3-dihydro-1H-indole-1-carbonyl]-2,3-dihydro-1H-indole-1-carboxylate

• ChemBase ID: 165341
• Molecular Formular: C38H44N4O8
• Molecular Mass: 684.77796
• Monoisotopic Mass: 684.31591439
• SMILES: c1ccc2c(c1)N([C@@H](C2)C(=O)N1[C@@H](Cc2c1cccc2)C(=O)N[C@H](C(=O)OC)CCCCNC(=O)OCc1ccccc1)C(=O)OC(C)(C)C
• Canonical SMILES: COC(=O)[C@@H](NC(=O)[C@@H]1Cc2c(N1C(=O)[C@@H]1Cc3c(N1C(=O)OC(C)(C)C)cccc3)cccc2)CCCCNC(=O)OCc1ccccc1
• InChI: InChI=1S/C38H44N4O8/c1-38(2,3)50-37(47)42-30-20-11-9-17-27(30)23-32(42)34(44)41-29-19-10-8-16-26(29)22-31(41)33(43)40-28(35(45)48-4)18-12-13-21-39-36(46)49-24-25-14-6-5-7-15-25/h5-11,14-17,19-20,28,31-32H,12-13,18,21-24H2,1-4H3,(H,39,46)(H,40,43)/t28-,31-,32-/m0/s1
• InChIKey: GKYGBJABPHBINI-MHDHXZMLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl (2S)-2-[(2S)-2-{[(2S)-6-{[(benzyloxy)carbonyl]amino}-1-methoxy-1-oxohexan-2-yl]carbamoyl}-2,3-dihydro-1H-indole-1-carbonyl]-2,3-dihydro-1H-indole-1-carboxylate
• IUPAC Traditional name: tert-butyl (2S)-2-[(2S)-2-{[(2S)-6-{[(benzyloxy)carbonyl]amino}-1-methoxy-1-oxohexan-2-yl]carbamoyl}-2,3-dihydroindole-1-carbonyl]-2,3-dihydroindole-1-carboxylate
• Synonyms: (2S)-2-[[(2S)-2,3-Dihydro-2-[[[(1S)-1-(methoxycarbonyl)-5-[[(phenylmethoxy)carbonyl]amino]pentyl]amino]carbonyl]-1H-indol-1-yl]carbonyl]-2,3-dihydro-1H-Indole-1-carboxylic Acid 1,1-Dimethylethyl Ester; D-43787

Database IDs

• CAS Number: 198016-44-3
• PubChem SID: 162259474
• PubChem CID: 9961556

CALCULATED PROPERTIES

• Acid pKa: 10.467125
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 5.1463776
• LogD (pH = 7.4): 5.146013
• Log P: 5.1463823
• Molar Refractivity: 184.197 cm^3
• Polarizability: 71.87658 Å^3
• Polar Surface Area: 143.58 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D100080

A novel immunomodulating compound; antiasthmatic and immunosuppressant.

REFERENCES

• Blackham, A., et al.: Clin. Exp. Immunol., 86, 224 (1991)
• Barnes, P., et al.: Clin. Sci., 1998, 94, 557 (1991)
• Cohn, L., et al.: Pharmacol. Ther., 88, 187 (1991)
• Asanuma, F., et al.: Inflamm. Res., 50, 136 (1991)
• Zenke, G., et al.: J. Immunol., 166,