(19R)-10,19-diethyl-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: 177796
• Molecular Formular: C22H20N2O5
• Molecular Mass: 392.4046
• Monoisotopic Mass: 392.13722175
• SMILES: c1(ccc2c(c1)c(c1c(n2)c2n(C1)c(=O)c1c(c2)[C@](C(=O)OC1)(O)CC)CC)O
• Canonical SMILES: CC[C@]1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4c(c3Cn1c2=O)CC)O
• InChI: InChI=1S/C22H20N2O5/c1-3-12-13-7-11(25)5-6-17(13)23-19-14(12)9-24-18(19)8-16-15(20(24)26)10-29-21(27)22(16,28)4-2/h5-8,25,28H,3-4,9-10H2,1-2H3/t22-/m1/s1
• InChIKey: FJHBVJOVLFPMQE-JOCHJYFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (19R)-10,19-diethyl-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: (19R)-10,19-diethyl-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: (4R)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)dione; (R)-SN-38

Database IDs

• CAS Number: 647852-82-2
• PubChem SID: 164233706
• PubChem CID: 13374085

CALCULATED PROPERTIES

• Acid pKa: 9.659211
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.8634372
• LogD (pH = 7.4): 1.8721043
• Log P: 1.874668
• Molar Refractivity: 106.1156 cm^3
• Polarizability: 41.40167 Å^3
• Polar Surface Area: 99.96 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S589945

R-Enantiomer of SN-38. Used for making the bioconjugates and bifunctional isocyanate cross linking reagents.

REFERENCES

• Billecke, S., et al.: Drug Metab. Dispos., 28, 1335 (2000)
• Teiber, J., et al.: Biochem. Pharmacol., 66, 887 (2000)
• Ashley, G., et al.: J. Antibiot., 57, 224 (2000)