(19S)-10,19-diethyl-12,19-dihydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate

• ChemBase ID: 170596
• Molecular Formular: C33H38N4O7
• Molecular Mass: 602.67742
• Monoisotopic Mass: 602.27404958
• SMILES: C1CCCN(C1)C1CCN(CC1)C(=O)Oc1ccc2c(c1)c(c1c(n2)c2n(C1O)c(=O)c1c(c2)[C@@](C(=O)OC1)(O)CC)CC
• Canonical SMILES: CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4c(c3C(n1c2=O)O)CC)OC(=O)N1CCC(CC1)N1CCCCC1
• InChI: InChI=1S/C33H38N4O7/c1-3-21-22-16-20(44-32(41)36-14-10-19(11-15-36)35-12-6-5-7-13-35)8-9-25(22)34-28-26-17-24-23(18-43-31(40)33(24,42)4-2)29(38)37(26)30(39)27(21)28/h8-9,16-17,19,30,39,42H,3-7,10-15,18H2,1-2H3/t30?,33-/m0/s1
• InChIKey: XQUUJPQAMJFQHV-OQGPVULJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (19S)-10,19-diethyl-12,19-dihydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^2,^1^1.0^4,^9.0^1^5,^2^0]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate
• IUPAC Traditional name: (19S)-10,19-diethyl-12,19-dihydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^2,^1^1.0^4,^9.0^1^5,^2^0]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate
• Synonyms: [1,4'-Bipiperidine]-1'-carboxylic Acid (4S)-4,11-diethyl-3,4,12,14-tetrahydro- 4,12-dihydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl Ester; (4S)-4,11-Diethyl-4,12-dihydroxy-9-[(4-piperidinopiperidino)carbonyloxy]-1H-pyrano[3’,4’:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; RPR 112524; Irinotecan 12-Hydroxy Impurity; 12-Hydroxy Irinotecan

Database IDs

• CAS Number: 185336-12-3
• PubChem SID: 164226506
• PubChem CID: 58730919

CALCULATED PROPERTIES

• Acid pKa: 11.629578
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.9681749
• LogD (pH = 7.4): 0.35160282
• Log P: 2.412249
• Molar Refractivity: 162.3602 cm^3
• Polarizability: 63.637005 Å^3
• Polar Surface Area: 132.74 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H943545

A metabolite of Irinotecan (I767500) found in human bile and urine.

REFERENCES

• Lokeic, F. et al.: Clin. Cancer Res., 2, 1943 (1996)
• Dodds, H.M. et al.: Anti-cancer Drug Des., 16, 239 (1996)
• Kunimoto, T., et al.: Cancer Res., 47, 5944 (1996)
• Shimada, Y., et al.: J. Clin. Oncol., 11, 909 (1996)