15-methoxy-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(13),2,4(8),9,11,14,16,21,23-nonaen-24-ium chloride

• ChemBase ID: 164028
• Molecular Formular: C21H16ClNO5
• Molecular Mass: 397.80844
• Monoisotopic Mass: 397.0717003
• SMILES: c12c(cc3c(c1)c1c(cc3)c3c(c[n+]1C)c1c(cc3OC)OCO1)OCO2.[Cl-]
• Canonical SMILES: COc1cc2OCOc2c2c1c1ccc3c(c1[n+](c2)C)cc1c(c3)OCO1.[Cl-]
• InChI: InChI=1S/C21H16NO5.ClH/c1-22-8-14-19(17(23-2)7-18-21(14)27-10-26-18)12-4-3-11-5-15-16(25-9-24-15)6-13(11)20(12)22;/h3-8H,9-10H2,1-2H3;1H/q+1;/p-1
• InChIKey: METXFOLRORBRGD-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 15-methoxy-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^2,^1^0.0^4,^8.0^1^4,^2^2.0^1^7,^2^1]tetracosa-1(13),2,4(8),9,11,14,16,21,23-nonaen-24-ium chloride
• IUPAC Traditional name: chelirubine chloride
• Synonyms: 5-Methoxy-13-methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium Chloride; Bocconine Chloride; Chelirubin Chloride; NSC 613395; Chelirubine Chloride

Database IDs

• CAS Number: 30044-85-0
• PubChem SID: 162258163
• PubChem CID: 356658

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -1.1011679
• LogD (pH = 7.4): -1.1011679
• Log P: -1.1011679
• Molar Refractivity: 97.2816 cm^3
• Polarizability: 41.449627 Å^3
• Polar Surface Area: 50.03 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C291850

Chelidonine quaternary ammonium reaction product with thiotepa was subjected to a number of pharmacological tests including anticancer activity. These quaternized alkaloids were claimed for use in the treatment of immunological or metabolic dysfunction, c

REFERENCES

• Sen, A., et al.: Biochem. Pharmacol., 48, 209 (1994)
• Panzer, A., et al.: Cancer Lett., 160, 149 (1994)
• Slaninova, I., et al.: Cell Biol. Toxicol., 17, 51 (1994)
• Slaninova, I., et al.: Pharma. Biol., 45, 131 (1994)