(2R,3R)-4-methylidene-2-octyl-5-oxooxolane-3-carboxylic acid

• ChemBase ID: 178385
• Molecular Formular: C14H22O4
• Molecular Mass: 254.32208
• Monoisotopic Mass: 254.15180918
• SMILES: C1(=C)[C@H]([C@H](OC1=O)CCCCCCCC)C(=O)O
• Canonical SMILES: CCCCCCCC[C@H]1OC(=O)C(=C)[C@H]1C(=O)O
• InChI: InChI=1S/C14H22O4/c1-3-4-5-6-7-8-9-11-12(13(15)16)10(2)14(17)18-11/h11-12H,2-9H2,1H3,(H,15,16)/t11-,12-/m1/s1
• InChIKey: VCWLZDVWHQVAJU-VXGBXAGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-4-methylidene-2-octyl-5-oxooxolane-3-carboxylic acid
• IUPAC Traditional name: (2R,3R)-4-methylidene-2-octyl-5-oxooxolane-3-carboxylic acid
• Synonyms: (2R,3S)-rel-Tetrahydro-4-methylene-2-octyl-5-oxo-3-furancarboxylic Acid; C 75; trans-C 75; trans-Tetrahydro-4-methylene-2-octyl-5-oxo-3-furancarboxylic Acid

Database IDs

• CAS Number: 191282-48-1
• PubChem SID: 164234295
• PubChem CID: 24728613

CALCULATED PROPERTIES

• Acid pKa: 4.2400293
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.538477
• LogD (pH = 7.4): 0.81354046
• Log P: 3.8193536
• Molar Refractivity: 67.3207 cm^3
• Polarizability: 26.84367 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T293960

trans-Tetrahydro-4-methylene-2-octyl-5-oxo-3-furancarboxylic Acid is a well-known fatty acid synthase (FAS) inhibitor. Studies show that trans-Tetrahydro-4-methylene-2-octyl-5-oxo-3-furancarboxylic Acid is a cell cycle arrest inducer in hepatocellular car

REFERENCES

• Rae, C. et al.: DIab. Obes. Metab., 10, 1271 (2008)
• Gao, Y. et al.: Cancer Biol. Ther., 5, 978 (2008)
• Flavin, R. et al.: Fut. Oncol., 6, 551 (2008)