2-[(1S)-1,8-diethyl-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl]acetic acid

• ChemBase ID: 168802
• Molecular Formular: C17H21NO3
• Molecular Mass: 287.35354
• Monoisotopic Mass: 287.15214354
• SMILES: c12c3c([nH]c1c(ccc2)CC)[C@](OCC3)(CC)CC(=O)O
• Canonical SMILES: CC[C@]1(OCCc2c1[nH]c1c2cccc1CC)CC(=O)O
• InChI: InChI=1S/C17H21NO3/c1-3-11-6-5-7-12-13-8-9-21-17(4-2,10-14(19)20)16(13)18-15(11)12/h5-7,18H,3-4,8-10H2,1-2H3,(H,19,20)/t17-/m0/s1
• InChIKey: NNYBQONXHNTVIJ-KRWDZBQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S)-1,8-diethyl-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl]acetic acid
• IUPAC Traditional name: (+)-etodolac
• Synonyms: (1S)-1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic Acid; (+)-(S)-Etodolac; (+)-Etodolac; (+)-Etodolic Acid; (S)-(+)-Etodolic Acid; RAK 592; S-Etodolac; (S)-(+)-Etodolac

Database IDs

• CAS Number: 87249-11-4
• PubChem SID: 162262934
• PubChem CID: 688461

CALCULATED PROPERTIES

• Acid pKa: 4.726933
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.603543
• LogD (pH = 7.4): 0.82613367
• Log P: 3.4435265
• Molar Refractivity: 81.1573 cm^3
• Polarizability: 32.41477 Å^3
• Polar Surface Area: 62.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E933095

The S-enantiomer of Etodolac (E933090). Anti-inflammatory; analgesic.

REFERENCES

• Boxenbaum, H., et al.: J. Pharmacokin. Biopharm., 10, 201 (1982)
• Iwatsubo, T., et al.: Biopharm. Drug Dispos., 17, 273 (1982)
• Obach, R., et al.: J. Pharmacol. Exp. Ther., 283, 46 (1982)