1,3-bis({2-[(1S)-1-(chloromethyl)-5-hydroxy-8-methyl-1H,2H,3H,6H-pyrrolo[3,2-e]indole-3-carbonyl]-1H-indol-5-yl})urea

• ChemBase ID: 162445
• Molecular Formular: C43H36Cl2N8O5
• Molecular Mass: 815.70254
• Monoisotopic Mass: 814.21857165
• SMILES: c12c(cc(cc1)NC(=O)Nc1cc3c(cc1)[nH]c(c3)C(=O)N1C[C@H](c3c1cc(c1c3c(c[nH]1)C)O)CCl)cc([nH]2)C(=O)N1C[C@H](c2c1cc(c1c2c(c[nH]1)C)O)CCl
• Canonical SMILES: ClC[C@@H]1CN(c2c1c1c(C)c[nH]c1c(c2)O)C(=O)c1[nH]c2c(c1)cc(cc2)NC(=O)Nc1ccc2c(c1)cc([nH]2)C(=O)N1C[C@H](c2c1cc(O)c1c2c(C)c[nH]1)CCl
• InChI: InChI=1S/C43H36Cl2N8O5/c1-19-15-46-39-33(54)11-31-37(35(19)39)23(13-44)17-52(31)41(56)29-9-21-7-25(3-5-27(21)50-29)48-43(58)49-26-4-6-28-22(8-26)10-30(51-28)42(57)53-18-24(14-45)38-32(53)12-34(55)40-36(38)20(2)16-47-40/h3-12,15-16,23-24,46-47,50-51,54-55H,13-14,17-18H2,1-2H3,(H2,48,49,58)/t23-,24-/m1/s1
• InChIKey: FONKWHRXTPJODV-DNQXCXABSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-bis({2-[(1S)-1-(chloromethyl)-5-hydroxy-8-methyl-1H,2H,3H,6H-pyrrolo[3,2-e]indole-3-carbonyl]-1H-indol-5-yl})urea
• IUPAC Traditional name: 1,3-bis({2-[(1S)-1-(chloromethyl)-5-hydroxy-8-methyl-1H,2H,6H-pyrrolo[3,2-e]indole-3-carbonyl]-1H-indol-5-yl})urea
• Synonyms: N,N'-Bis[2-[[(1S)-1-(chloromethyl)-1,6-dihydro-5-hydroxy-8-methylbenzo[1,2-b:4,3-b']dipyrrol-3(2H)-yl]carbonyl]-1H-indol-5-yl]urea; (8S,8'S)-6,6'-[Carbonylbis(imino-1H-indole-5,2-diylcarbonyl)]bis[8-(chloromethyl)-3,6,7,8-tetrahydro-1-methylbenzo[1,2-b:4,3-b']dipyrrol-4-ol; NSC 615291; U 77779; Bizelesin

Database IDs

• CAS Number: 129655-21-6
• PubChem SID: 162256580
• PubChem CID: 60794

CALCULATED PROPERTIES

• Acid pKa: 8.443186
• H Acceptors: 5
• H Donor: 8
• LogD (pH = 5.5): 6.4134903
• LogD (pH = 7.4): 6.3757873
• Log P: 6.413982
• Molar Refractivity: 226.821 cm^3
• Polarizability: 88.08363 Å^3
• Polar Surface Area: 185.37 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B591700

As members of the cyclopropylpyrroloindole family, Adozelesin and Bizelesin cause genomic DNA lesions by alkylating DNA. Adozelesin induces single-strand DNA lesions, whereas Bizelesin induces both single-strand lesions and double-strand DNA cross-links.

REFERENCES

• Lee, C., et al.: Cancer Res., 51, 6586 (1991)
• McHugh, M., et al.: Biochemistry, 38, 11508 (1991)
• Liu, J., et al.: J. Biol. Chem., 275, 1391 (1991)