[4-(4-{[(5Z)-3-[(4-fluorophenyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl}phenoxymethyl)phenyl]boronic acid

• ChemBase ID: 169822
• Molecular Formular: C24H19BFNO5S
• Molecular Mass: 463.2857632
• Monoisotopic Mass: 463.10610233
• SMILES: C1(=O)S/C(=C\c2ccc(cc2)OCc2ccc(cc2)B(O)O)/C(=O)N1Cc1ccc(cc1)F
• Canonical SMILES: Fc1ccc(cc1)CN1C(=O)S/C(=C\c2ccc(cc2)OCc2ccc(cc2)B(O)O)/C1=O
• InChI: InChI=1S/C24H19BFNO5S/c26-20-9-3-17(4-10-20)14-27-23(28)22(33-24(27)29)13-16-5-11-21(12-6-16)32-15-18-1-7-19(8-2-18)25(30)31/h1-13,30-31H,14-15H2/b22-13-
• InChIKey: BRWUZCBSWABPMR-XKZIYDEJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [4-(4-{[(5Z)-3-[(4-fluorophenyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl}phenoxymethyl)phenyl]boronic acid
• IUPAC Traditional name: 4-(4-{[(5Z)-3-[(4-fluorophenyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl}phenoxymethyl)phenylboronic acid
• Synonyms: B-[3-[[4-[[3-[(4-Fluorophenyl)methyl]-2,4-dioxo-5-thiazolidinylidene]methyl]phenoxy]methyl]phenyl]boronic Acid; HA 150

Database IDs

• CAS Number: 1229652-21-4
• PubChem SID: 162263954
• PubChem CID: 46856189

CALCULATED PROPERTIES

• Acid pKa: 8.746438
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 4.8013554
• LogD (pH = 7.4): 4.782571
• Log P: 4.8016
• Molar Refractivity: 121.568 cm^3
• Polarizability: 47.602325 Å^3
• Polar Surface Area: 87.07 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H011600

HA 150 is a selective boronic acid-based inhibitor of autotaxin. Studies show that adminstration of HA 150 in mice results in rapid decrease of the lipid mediator lysophosphatidic acid (LPA) in the circulation. These findings suggest that HA 150 may provi

REFERENCES

• Albers, H.M.H.G. et al.: Proc. Natl. Acad Sci. USA, 107, 7257 (2010)
• Albers, H.M.H.G. et al.: J. Med. Chem., 53, 4958 (2010)