(19S)-19-(2H5)ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione

• ChemBase ID: 170317
• Molecular Formular: C20H16N2O5
• Molecular Mass: 364.35144
• Monoisotopic Mass: 364.10592162
• SMILES: c1c(ccc2c1cc1c(n2)c2n(C1)c(=O)c1c(c2)[C@@](C(=O)OC1)(O)CC)O
• Canonical SMILES: CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4cc3Cn1c2=O)O
• InChI: InChI=1S/C20H16N2O5/c1-2-20(26)14-7-16-17-11(5-10-6-12(23)3-4-15(10)21-17)8-22(16)18(24)13(14)9-27-19(20)25/h3-7,23,26H,2,8-9H2,1H3/t20-/m0/s1
• InChIKey: HAWSQZCWOQZXHI-FQEVSTJZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (19S)-19-(^2H₅)ethyl-7,19-dihydroxy-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)-heptaene-14,18-dione
• IUPAC Traditional name: (19S)-19-(^2H₅)ethyl-7,19-dihydroxy-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)-heptaene-14,18-dione
• Synonyms: (4S)-4-(Ethyl-d5)-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; (S)-10-Hydroxycamptothecin-d5; Hydroxycamptothecin-d5; NSC 107124-d5; 10-Hydroxy Camptothecin-d5

Database IDs

• PubChem SID: 164226227
• PubChem CID: 71748919

CALCULATED PROPERTIES

• Acid pKa: 9.654745
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.9146374
• LogD (pH = 7.4): 0.9142485
• Log P: 0.9166779
• Molar Refractivity: 96.4734 cm^3
• Polarizability: 37.803802 Å^3
• Polar Surface Area: 99.96 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide
• Apperance: Blue Solid

DETAILS

Toronto Research Chemicals - H875002

A labelled Camptothecin derivative; a topoisomerase inhibitor for cancer therapy.

REFERENCES

• Wani, M.C., et al.: J. Med. Chem., 29, 2358 (1986)
• Miller, K.D., et al.: Invest. New Drugs, 22, 69 (1986)
• Punt, C.J.A., et al.: Eur. J. Cancer, 40, 1332 (1986)
• Wang, J.-Q., et al.: Bioorg. Med. Chem., 13, 549 (1986)