4'-(2H5)ethyl-4'-hydroxy-1',3',4',7',8',10'-hexahydrospiro[1,3-dioxolane-2,6'-pyrano[3,4-f]indolizine]-3',10'-dione

• ChemBase ID: 168528
• Molecular Formular: C15H17NO6
• Molecular Mass: 307.29858
• Monoisotopic Mass: 307.10558727
• SMILES: n12c(cc3c(c1=O)COC(=O)C3(O)CC)C1(CC2)OCCO1
• Canonical SMILES: CCC1(O)C(=O)OCc2c1cc1n(c2=O)CCC21OCCO2
• InChI: InChI=1S/C15H17NO6/c1-2-14(19)10-7-11-15(21-5-6-22-15)3-4-16(11)12(17)9(10)8-20-13(14)18/h7,19H,2-6,8H2,1H3
• InChIKey: GHFZMAJAVDXFDR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4'-(^2H₅)ethyl-4'-hydroxy-1',3',4',7',8',10'-hexahydrospiro[1,3-dioxolane-2,6'-pyrano[3,4-f]indolizine]-3',10'-dione
• IUPAC Traditional name: 4'-(^2H₅)ethyl-4'-hydroxy-7',8'-dihydro-1'H-spiro[1,3-dioxolane-2,6'-pyrano[3,4-f]indolizine]-3',10'-dione
• Synonyms: (±)-4'-Ethyl-7',8'-dihydro-4'-hydroxy-spiro[1,3-dioxolane-2,6'(3'H)-[1H]pyrano[3,4-f]indolizine]-3',10'(4'H)-dione-d5; 4'-Ethyl-7',8'-dihydro-4'-hydroxy-spiro[1,3-dioxolane-2,6'(3'H)-[1H]pyrano[3,4-f]indolizine]-3',10'(4'H)-dione-d5

Database IDs

• PubChem SID: 162262660
• PubChem CID: 71316568

CALCULATED PROPERTIES

• Acid pKa: 11.710747
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.13364184
• LogD (pH = 7.4): -0.13366279
• Log P: -0.13364157
• Molar Refractivity: 75.222 cm^3
• Polarizability: 29.089802 Å^3
• Polar Surface Area: 85.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloroform; Methanol
• Apperance: Off-white Solid

DETAILS

Toronto Research Chemicals - E917312

Used in the preparation of Camptothecin and Homocamptothecin derivatives, for their therapeutic use as antitumor agents.

REFERENCES

• Wani, M.C., et al.: J. Med. Chem., 29, 2358 (1986)
• Miller, K.D., et al.: Invest. New Drugs, 22, 69 (1986)
• Punt, C.J.A., et al.: Eur. J. Cancer, 40, 1332 (1986)
• Wang, J.-Q., et al.: Bioorg. Med. Chem., 13, 549 (2005)