(19S)-10,19-diethyl-19-hydroxy-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 2-hydroxy-4-(piperidin-1-yl)piperidine-1-carboxylate

• ChemBase ID: 170675
• Molecular Formular: C33H38N4O7
• Molecular Mass: 602.67742
• Monoisotopic Mass: 602.27404958
• SMILES: C1CCCN(C1)C1CCN(C(C1)O)C(=O)Oc1ccc2c(c1)c(c1c(n2)c2n(C1)c(=O)c1c(c2)[C@@](C(=O)OC1)(O)CC)CC
• Canonical SMILES: CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4c(c3Cn1c2=O)CC)OC(=O)N1CCC(CC1O)N1CCCCC1
• InChI: InChI=1S/C33H38N4O7/c1-3-21-22-15-20(44-32(41)36-13-10-19(14-28(36)38)35-11-6-5-7-12-35)8-9-26(22)34-29-23(21)17-37-27(29)16-25-24(30(37)39)18-43-31(40)33(25,42)4-2/h8-9,15-16,19,28,38,42H,3-7,10-14,17-18H2,1-2H3/t19?,28?,33-/m0/s1
• InChIKey: DDBHYRUFETXXKP-JSLFILEWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (19S)-10,19-diethyl-19-hydroxy-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 2-hydroxy-4-(piperidin-1-yl)piperidine-1-carboxylate
• IUPAC Traditional name: (19S)-10,19-diethyl-19-hydroxy-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 2-hydroxy-4-(piperidin-1-yl)piperidine-1-carboxylate
• Synonyms: (4S)-4,11-Diethyl-4-hydroxy-9-[(2-hydroxy-4-piperidinopiperidino)carbonyloxy]-1H-pyrano[3’,4’:6,7]indolizino[1,2-b]-quinoline-3,14(4H,12H)-dione; Irinotecan 2-Hydroxy Impurity; 2-Hydroxy Irinotecan

Database IDs

• PubChem SID: 164226585
• PubChem CID: 58730923

CALCULATED PROPERTIES

• Acid pKa: 11.701231
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.6005007
• LogD (pH = 7.4): 0.98808914
• Log P: 2.6225924
• Molar Refractivity: 161.9466 cm^3
• Polarizability: 63.640774 Å^3
• Polar Surface Area: 132.74 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H943540

A hydroxy impurity of Irinotecan (I767500).

REFERENCES

• Kunimoto, T., et al.: Cancer Res., 47, 5944 (1987)
• Shimada, Y., et al.: J. Clin. Oncol., 11, 909 (1993)