tert-butyl 3-[(2S,5S,8S)-14-methoxy-2-(2-methylpropyl)-4,7-dioxo-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraen-5-yl]propanoate

• ChemBase ID: 172138
• Molecular Formular: C26H35N3O5
• Molecular Mass: 469.5732
• Monoisotopic Mass: 469.25767124
• SMILES: N1[C@H](C(=O)N2[C@H](C1=O)Cc1c([C@@H]2CC(C)C)[nH]c2c1ccc(c2)OC)CCC(=O)OC(C)(C)C
• Canonical SMILES: COc1ccc2c(c1)[nH]c1c2C[C@@H]2N([C@H]1CC(C)C)C(=O)[C@@H](NC2=O)CCC(=O)OC(C)(C)C
• InChI: InChI=1S/C26H35N3O5/c1-14(2)11-20-23-17(16-8-7-15(33-6)12-19(16)27-23)13-21-24(31)28-18(25(32)29(20)21)9-10-22(30)34-26(3,4)5/h7-8,12,14,18,20-21,27H,9-11,13H2,1-6H3,(H,28,31)/t18-,20-,21-/m0/s1
• InChIKey: NXNRAECHCJZNRF-JBACZVJFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl 3-[(2S,5S,8S)-14-methoxy-2-(2-methylpropyl)-4,7-dioxo-3,6,17-triazatetracyclo[8.7.0.0^3,^8.0^1^1,^1^6]heptadeca-1(10),11,13,15-tetraen-5-yl]propanoate
• IUPAC Traditional name: tert-butyl 3-[(2S,5S,8S)-14-methoxy-2-(2-methylpropyl)-4,7-dioxo-3,6,17-triazatetracyclo[8.7.0.0^3,^8.0^1^1,^1^6]heptadeca-1(10),11,13,15-tetraen-5-yl]propanoate
• Synonyms: (3S,6S,12aS)-,2,3,4,6,7,12,12a-Octahydro-9-methoxy-6-(2-methylpropyl)-1,4-dioxopyrazino[1',2':1,6]pyrido[3,4-b]indole-3-propanoic Acid 1,1-Dimethylethyl Ester; KO 143

Database IDs

• CAS Number: 461054-93-3
• PubChem SID: 164228048
• PubChem CID: 10322450

CALCULATED PROPERTIES

• Acid pKa: 11.2008095
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.936671
• LogD (pH = 7.4): 2.936611
• Log P: 2.9366717
• Molar Refractivity: 127.5498 cm^3
• Polarizability: 51.07516 Å^3
• Polar Surface Area: 100.73 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - K655000

A potent BCRP (breast cancer resistance protein) inhibitor.

REFERENCES

• Allen, J., et al.: Cancer Res., 59, 4237 (1999)
• van Loevezijn, A., et al.: Bioorg. Med. Chem. Lett., 11, 29 (1999)
• Raaijmakers, M., et al.: Clin. Cancer Res., 11, 2436 (1999)