(1R,2S,3R,4S)-2,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid

• ChemBase ID: 132839
• Molecular Formular: C10H14O5
• Molecular Mass: 214.21516
• Monoisotopic Mass: 214.08412355
• SMILES: C[C@]1([C@H]2CC[C@@H]([C@]1(C)C(=O)O)O2)C(=O)O
• Canonical SMILES: OC(=O)[C@]1(C)[C@H]2CC[C@@H]([C@]1(C)C(=O)O)O2
• InChI: InChI=1S/C10H14O5/c1-9(7(11)12)5-3-4-6(15-5)10(9,2)8(13)14/h5-6H,3-4H2,1-2H3,(H,11,12)(H,13,14)/t5-,6+,9+,10-
• InChIKey: NMTNUQBORQILRK-XCVPVQRUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,3R,4S)-2,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid
• IUPAC Traditional name: (1R,2S,3R,4S)-2,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid
• Synonyms: Cantharidic acid

Database IDs

• CAS Number: 28874-45-5
• MDL Number: MFCD00047137
• PubChem SID: 24278339; 162227116
• PubChem CID: 121475

CALCULATED PROPERTIES

• Acid pKa: 3.6802602
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.0993943
• LogD (pH = 7.4): -4.0842485
• Log P: 0.92501104
• Molar Refractivity: 48.6087 cm^3
• Polarizability: 19.585539 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; ethanol: soluble

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 38
• Safety Statements: 22-36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

DETAILS

Sigma Aldrich - C8088

Biochem/physiol Actions
Useful for inhibiting PP1 and PP2A during purification of phosphorylated proteins, IC50 = 53 nM.