2-{1,8-diethyl-4-oxo-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetic acid

• ChemBase ID: 176012
• Molecular Formular: C17H19NO4
• Molecular Mass: 301.33706
• Monoisotopic Mass: 301.13140809
• SMILES: c12c3c([nH]c1c(ccc2)CC)C(OCC3=O)(CC)CC(=O)O
• Canonical SMILES: CCC1(OCC(=O)c2c1[nH]c1c2cccc1CC)CC(=O)O
• InChI: InChI=1S/C17H19NO4/c1-3-10-6-5-7-11-14-12(19)9-22-17(4-2,8-13(20)21)16(14)18-15(10)11/h5-7,18H,3-4,8-9H2,1-2H3,(H,20,21)
• InChIKey: HNWLARFJUBQIQT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{1,8-diethyl-4-oxo-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetic acid
• IUPAC Traditional name: {1,8-diethyl-4-oxo-3H,9H-pyrano[3,4-b]indol-1-yl}acetic acid
• Synonyms: 1,8-Diethyl-4-oxo-1,3,4,9-tetrahydro-pyrano[3,4-b]indole-1-acetic Acid; 4-Oxo Etodolac

Database IDs

• CAS Number: 111478-86-5
• PubChem SID: 164231922
• PubChem CID: 11266595

CALCULATED PROPERTIES

• Acid pKa: 4.3846493
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.5168499
• LogD (pH = 7.4): -0.23717974
• Log P: 2.6626143
• Molar Refractivity: 81.6914 cm^3
• Polarizability: 32.553455 Å^3
• Polar Surface Area: 79.39 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 195-197°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - O856800

A metabolite of Etodolac (E933090).

REFERENCES

• Chan, et al.: J. Pharmacol., Exp. Ther., 274, 1531 (1995)
• Dajani, et al.: J. Physiol. Pharmacol., 46, 3 (1995)
• Sano, et al.: Cancer Res., 55, 3785 (1995)