(4S)-4-(2H5)ethyl-4-hydroxy-1H,3H,4H,6H,7H,8H,10H-pyrano[3,4-f]indolizine-3,6,10-trione

• ChemBase ID: 168527
• Molecular Formular: C13H13NO5
• Molecular Mass: 263.24602
• Monoisotopic Mass: 263.07937252
• SMILES: n12c(cc3c(c1=O)COC(=O)[C@]3(O)CC)C(=O)CC2
• Canonical SMILES: CC[C@@]1(O)C(=O)OCc2c1cc1C(=O)CCn1c2=O
• InChI: InChI=1S/C13H13NO5/c1-2-13(18)8-5-9-10(15)3-4-14(9)11(16)7(8)6-19-12(13)17/h5,18H,2-4,6H2,1H3/t13-/m0/s1
• InChIKey: IGKWOGMVAOYVSJ-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-(^2H₅)ethyl-4-hydroxy-1H,3H,4H,6H,7H,8H,10H-pyrano[3,4-f]indolizine-3,6,10-trione
• IUPAC Traditional name: (4S)-4-(^2H₅)ethyl-4-hydroxy-1H,7H,8H-pyrano[3,4-f]indolizine-3,6,10-trione
• Synonyms: (S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione-d5; (4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione-d5; (4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione-d5

Database IDs

• PubChem SID: 162262659
• PubChem CID: 71316567

CALCULATED PROPERTIES

• Acid pKa: 11.708805
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.47680008
• LogD (pH = 7.4): -0.47682112
• Log P: -0.47679982
• Molar Refractivity: 65.7022 cm^3
• Polarizability: 24.798914 Å^3
• Polar Surface Area: 83.91 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Dark Yellow Solid

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E917302

Used in the preparation of Camptothecin derivatives, for their therapeutic use as antitumor agents.

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)