5,13-diethyl-7,9-dioxo-6-oxa-10,20-diazapentacyclo[10.8.0.02,10.04,8.014,19]icosa-1(20),2,4(8),12,14,16,18-heptaen-16-yl 4-(piperidin-1-yl)piperidine-1-carboxylate

• ChemBase ID: 171746
• Molecular Formular: C32H36N4O5
• Molecular Mass: 556.65204
• Monoisotopic Mass: 556.26857027
• SMILES: c1(ccc2c(c1)c(c1c(n2)c2n(C1)c(=O)c1c(c2)C(OC1=O)CC)CC)OC(=O)N1CCC(CC1)N1CCCCC1
• Canonical SMILES: CCC1OC(=O)c2c1cc1c3nc4ccc(cc4c(c3Cn1c2=O)CC)OC(=O)N1CCC(CC1)N1CCCCC1
• InChI: InChI=1S/C32H36N4O5/c1-3-21-22-16-20(40-32(39)35-14-10-19(11-15-35)34-12-6-5-7-13-34)8-9-25(22)33-29-24(21)18-36-26(29)17-23-27(4-2)41-31(38)28(23)30(36)37/h8-9,16-17,19,27H,3-7,10-15,18H2,1-2H3
• InChIKey: MPKLBQKGQFVIOG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,13-diethyl-7,9-dioxo-6-oxa-10,20-diazapentacyclo[10.8.0.0^2,^1^0.0^4,^8.0^1^4,^1^9]icosa-1(20),2,4(8),12,14,16,18-heptaen-16-yl 4-(piperidin-1-yl)piperidine-1-carboxylate
• IUPAC Traditional name: 5,13-diethyl-7,9-dioxo-6-oxa-10,20-diazapentacyclo[10.8.0.0^2,^1^0.0^4,^8.0^1^4,^1^9]icosa-1(20),2,4(8),12,14,16,18-heptaen-16-yl 4-(piperidin-1-yl)piperidine-1-carboxylate
• Synonyms: [1,4'-Bipiperidine]-1'-carboxylic Acid 3,10-Diethyl-11,13-dihydro-1,13-dioxo-1H,3H- furo[3',4':6,7]indolizino[1,2-b]quinolin-8-yl Ester; Irinotecan Lactone Impurity

Database IDs

• CAS Number: 143490-53-3
• PubChem SID: 164227656
• PubChem CID: 58730920

CALCULATED PROPERTIES

• Acid pKa: 13.839683
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 0.3926123
• LogD (pH = 7.4): 1.7154609
• Log P: 3.7761397
• Molar Refractivity: 155.1484 cm^3
• Polarizability: 60.537445 Å^3
• Polar Surface Area: 92.28 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - I767520

A lactone impurity of Irinotecan (I767500), a DNA topoisomerase inhibitor. A photodegradation product of a camptothecin derivative used as an anticancer drug.

REFERENCES

• Akimoto, K. et al.: J. Chrom. 734, 401 (1996)
• Kunimoto, T., et al.: Cancer Res., 47, 5944 (1996)
• Shimada, Y., et al.: J. Clin. Oncol., 11, 909 (1996)
• Chen, A., et al.: Annu. Rev. Pharmacol. Toxicol., 34, 191 (1996)