(2E)-4-(2H3)methoxy-4-oxobut-2-enoic acid

• ChemBase ID: 169058
• Molecular Formular: C5H6O4
• Molecular Mass: 130.09874
• Monoisotopic Mass: 130.02660867
• SMILES: OC(=O)/C=C/C(=O)OC
• Canonical SMILES: COC(=O)/C=C/C(=O)O
• InChI: InChI=1S/C5H6O4/c1-9-5(8)3-2-4(6)7/h2-3H,1H3,(H,6,7)/b3-2+
• InChIKey: NKHAVTQWNUWKEO-NSCUHMNNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-4-(^2H₃)methoxy-4-oxobut-2-enoic acid
• IUPAC Traditional name: (2E)-4-(^2H₃)methoxy-4-oxobut-2-enoic acid
• Synonyms: (2E)-2-Butenedioic Acid 1-Methyl Ester-d3; (E)-2-Butenedioic Acid Monomethyl Ester-d3; Fumaric Acid Methyl Ester-d3; Methyl Hydrogen Fumarate-d3; Monomethyl Fumarate-d3; Fumaric Acid Monomethyl Ester-d3

Database IDs

• PubChem SID: 162263190
• PubChem CID: 50896236

CALCULATED PROPERTIES

• Acid pKa: 3.3100967
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.834956
• LogD (pH = 7.4): -3.0856297
• Log P: 0.33831304
• Molar Refractivity: 29.3761 cm^3
• Polarizability: 11.140744 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F500392

Labelled analogue of Fumaric Acid Monomethyl Ester, one of the most bioactive anti-psoriatic fumaric acid ester metabolite. Fumaric Acid Monomethyl Ester is potent nicotinic acid receptor agonist. Fumaric Acid Monomethyl Ester has also been shown to selec

REFERENCES

• Tang, H. et al.: Biochem. Biophys. Res. Comm., 375, 562 (2008)
• Litjens, N.H.R. et al.: Br. J. Dermatol., 154, 211 (2008)
• de Jong, R. et al.: Eur. J. Immunol., 26, 2067 (2008)