(2R,3R,4R,5S,6S)-6-{[(5E)-2,2-dimethyl-7-[methyl(naphthalen-1-ylmethyl)amino]hept-5-en-3-yn-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 171345
• Molecular Formular: C27H33NO7
• Molecular Mass: 483.55342
• Monoisotopic Mass: 483.2257024
• SMILES: c12c(cccc1CN(C/C=C/C#CC(CO[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)(C)C)C)cccc2
• Canonical SMILES: CN(Cc1cccc2c1cccc2)C/C=C/C#CC(CO[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)(C)C
• InChI: InChI=1S/C27H33NO7/c1-27(2,17-34-26-23(31)21(29)22(30)24(35-26)25(32)33)14-7-4-8-15-28(3)16-19-12-9-11-18-10-5-6-13-20(18)19/h4-6,8-13,21-24,26,29-31H,15-17H2,1-3H3,(H,32,33)/b8-4+/t21-,22-,23+,24-,26+/m1/s1
• InChIKey: XWKOYVRIRYSRSH-DSRSGAICSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6S)-6-{[(5E)-2,2-dimethyl-7-[methyl(naphthalen-1-ylmethyl)amino]hept-5-en-3-yn-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6S)-6-{[(5E)-2,2-dimethyl-7-[methyl(naphthalen-1-ylmethyl)amino]hept-5-en-3-yn-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (E)-2,2-Dimethyl-7-[methyl(1-naphthalenylmethyl)amino]-5-hepten-3-ynyl β-D-Glucopyranosiduronic Acid; Hydroxy Terbinafine β-D-Glucuronide

Database IDs

• CAS Number: 99473-12-8
• PubChem SID: 164227255
• PubChem CID: 71749360

CALCULATED PROPERTIES

• Acid pKa: 3.1297202
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.063984066
• LogD (pH = 7.4): 0.05529527
• Log P: 0.06474626
• Molar Refractivity: 132.1306 cm^3
• Polarizability: 52.348145 Å^3
• Polar Surface Area: 119.69 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Yellow Solid
• Melting Point: 105-107°C

DETAILS

Toronto Research Chemicals - H956175

A metabolite of Terbinafine, an orally active, antimycotic allylamine related to naftifine. A specfic inhibitor of squalene epoxidase, a key enzyme in fungal ergosterol biosynthesis.

REFERENCES

• Gazinger, U., et al.: Proc. 13th Int. Congr. Chemother., 6, 116/52 (1983)
• Shadomy, S., et al.: Sabouraudia, 23, 125 (1983)
• Evans, E.G.V., et al.: Brit. Med. J., 318, 1031 (1999)