2-{10-oxo-2-thiatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-6-yl}propanoic acid

• ChemBase ID: 179620
• Molecular Formular: C17H14O3S
• Molecular Mass: 298.35626
• Monoisotopic Mass: 298.06636531
• SMILES: S1c2c(C(=O)Cc3c1ccc(c3)C(C)C(=O)O)cccc2
• Canonical SMILES: OC(=O)C(c1ccc2c(c1)CC(=O)c1c(S2)cccc1)C
• InChI: InChI=1S/C17H14O3S/c1-10(17(19)20)11-6-7-15-12(8-11)9-14(18)13-4-2-3-5-16(13)21-15/h2-8,10H,9H2,1H3,(H,19,20)
• InChIKey: MUXFZBHBYYYLTH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{10-oxo-2-thiatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-6-yl}propanoic acid; 2-{10-oxo-2-thiatricyclo[9.4.0.0^3,^8]pentadeca-1(15),3,5,7,11,13-hexaen-6-yl}propanoic acid; 2-{10-oxo-2-thiatricyclo[9.4.0.0^3,^8]pentadeca-1(15),3(8),4,6,11,13-hexaen-6-yl}propanoic acid
• IUPAC Traditional name: 2-{10-oxo-2-thiatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-6-yl}propanoic acid; peon
• Synonyms: 10,11-Dihydro-α-methyl-10-oxodibenzo[b,f]thiepin-2-acetic Acid; 2-(10,11-Dihydro-10-oxodibenzo[b,f]thiepin-2-yl)propionic Acid; CN-100; Soreton; Peon; Zaltoprofen; 2-(10-Oxo-10,11-dihydrodibenzo[b,f]thiepin-2-yl)propanoic acid

Database IDs

• CAS Number: 74711-43-6
• PubChem SID: 164235530
• PubChem CID: 5720

CALCULATED PROPERTIES

• Acid pKa: 3.668548
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.9322828
• LogD (pH = 7.4): 0.44359788
• Log P: 3.7614713
• Molar Refractivity: 83.6909 cm^3
• Polarizability: 31.99242 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 129-131°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Target: COX

Product Information

• Purity: 95+%
• Salt Data: Free Base

DETAILS

Toronto Research Chemicals - Z146000

Anti-inflammatory activity resides in (S)-enantiomer.

REFERENCES

• Yamamoto, M., et al.: Chirality, 2, 280 (1990)
• Inoue, M., et al.: J Pharmacol. Exp. Ther., 293, 662 (1990)
• Graven-Nielsen, T., et al.: Clin. J. Pain, 17, 2 (1990)