5-{[1-({[(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]oxy}carbonyl)piperidin-4-yl]amino}pentanoic acid

• ChemBase ID: 168407
• Molecular Formular: C33H38N4O8
• Molecular Mass: 618.67682
• Monoisotopic Mass: 618.2689642
• SMILES: C1(CCN(CC1)C(=O)Oc1ccc2c(c1)c(c1c(n2)c2n(C1)c(=O)c1c(c2)[C@](C(=O)OC1)(CC)O)CC)NCCCCC(=O)O
• Canonical SMILES: CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4c(c3Cn1c2=O)CC)OC(=O)N1CCC(CC1)NCCCCC(=O)O
• InChI: InChI=1S/C33H38N4O8/c1-3-21-22-15-20(45-32(42)36-13-10-19(11-14-36)34-12-6-5-7-28(38)39)8-9-26(22)35-29-23(21)17-37-27(29)16-25-24(30(37)40)18-44-31(41)33(25,43)4-2/h8-9,15-16,19,34,43H,3-7,10-14,17-18H2,1-2H3,(H,38,39)/t33-/m0/s1
• InChIKey: BSVVZICJFYZDJJ-XIFFEERXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{[1-({[(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]oxy}carbonyl)piperidin-4-yl]amino}pentanoic acid
• IUPAC Traditional name: 5-{[1-({[(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]oxy}carbonyl)piperidin-4-yl]amino}pentanoic acid
• Synonyms: 4-[(4-Carboxybutyl)amino]-1-piperidinecarboxylic Acid (4S)-4,11-Diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl Ester-d3; APC-d3; RPR 121056-d3; 7-Ethyl-10-(4-N-aminopentanoic acid)-1-piperidino)carbonyloxycamptothecin-d3

Database IDs

• PubChem SID: 162262539
• PubChem CID: 46781526

CALCULATED PROPERTIES

• Acid pKa: 4.658114
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -0.5302573
• LogD (pH = 7.4): -0.481014
• Log P: -0.48129612
• Molar Refractivity: 164.0336 cm^3
• Polarizability: 64.283516 Å^3
• Polar Surface Area: 158.6 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 172-174°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E898902

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