(19S)-19-ethyl-10-[(2,2,2-2H3)ethyl]-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 4-aminopiperidine-1-carboxylate

• ChemBase ID: 168411
• Molecular Formular: C28H30N4O6
• Molecular Mass: 518.561
• Monoisotopic Mass: 518.2165347
• SMILES: NC1CCN(CC1)C(=O)Oc1ccc2c(c1)c(c1c(n2)c2n(C1)c(=O)c1c(c2)[C@](C(=O)OC1)(CC)O)CC
• Canonical SMILES: CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4c(c3Cn1c2=O)CC)OC(=O)N1CCC(CC1)N
• InChI: InChI=1S/C28H30N4O6/c1-3-17-18-11-16(38-27(35)31-9-7-15(29)8-10-31)5-6-22(18)30-24-19(17)13-32-23(24)12-21-20(25(32)33)14-37-26(34)28(21,36)4-2/h5-6,11-12,15,36H,3-4,7-10,13-14,29H2,1-2H3/t28-/m0/s1
• InChIKey: APWFTHDYKJHNEV-NDEPHWFRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (19S)-19-ethyl-10-[(2,2,2-^2H₃)ethyl]-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 4-aminopiperidine-1-carboxylate
• IUPAC Traditional name: (19S)-19-ethyl-10-[(2,2,2-^2H₃)ethyl]-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 4-aminopiperidine-1-carboxylate
• Synonyms: 4-Amino-(4S)-4-Ethyl-11-(ethyl-d3)-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl 1-Piperidinecarboxylic Acid Ester; RPR 132595A-d3; NPC-d3 (metabolite); 7-Ethyl-10-(4-amino-1-piperidino)carbonyloxycamptothecin-d3

Database IDs

• PubChem SID: 162262543
• PubChem CID: 46781527

CALCULATED PROPERTIES

• Acid pKa: 11.716885
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.9158231
• LogD (pH = 7.4): -1.3383697
• Log P: 0.99369514
• Molar Refractivity: 139.119 cm^3
• Polarizability: 54.537537 Å^3
• Polar Surface Area: 135.29 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: 178-184°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E899152

A major labelled metabolite of Irinotecan.

REFERENCES

• Canal, P., et al.: J. Clin. Oncol., 14, 2688 (1996)
• Haaz, M., et al.: Cancer Res., 58, 468 (1996)
• Kehrer, D., et al.: Clin. Cancer Res., 6, 3451 (1996)
• Hanioka, N., et al.: Xenobiotica, 31, 687 (1996)
• Satoh, T., et al.: Drug Metab. Dispos., 30, 488 (2