(2E)-4-[tris(2H3)methylazaniumyl]but-2-enoate

• ChemBase ID: 165040
• Molecular Formular: C7H13NO2
• Molecular Mass: 143.18362
• Monoisotopic Mass: 143.09462866
• SMILES: [O-]C(=O)/C=C/C[N+](C)(C)C
• Canonical SMILES: [O-]C(=O)/C=C/C[N+](C)(C)C
• InChI: InChI=1S/C7H13NO2/c1-8(2,3)6-4-5-7(9)10/h4-5H,6H2,1-3H3/b5-4+
• InChIKey: GUYHPGUANSLONG-SNAWJCMRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-4-[tris(^2H₃)methylazaniumyl]but-2-enoate
• IUPAC Traditional name: (2E)-4-[tris(^2H₃)methylammonio]but-2-enoate
• Synonyms: 3-Carboxy-N,N,N-trimethyl-2-propen-1-aminium-d9 Inner Salt; (3-Carboxyallyl)trimethylammonium-d9 Hydroxide Inner Salt; Croton Betaine-d9; Crotonic Acid Betaine-d9; Crotonobetaine-d9

Database IDs

• PubChem SID: 162259173
• PubChem CID: 71315008

CALCULATED PROPERTIES

• Acid pKa: 4.4913707
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -3.0776997
• LogD (pH = 7.4): -3.0446913
• Log P: -3.814779
• Molar Refractivity: 63.2171 cm^3
• Polarizability: 15.256077 Å^3
• Polar Surface Area: 40.13 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C818802

Labelled analogue of Crotonobetaine, a trimethylammonium compound that can be converted into L-Carnitine by Escherichia coli via stereoselective hydration.

REFERENCES

• Seim, H. et al.: Eur. Congr. Biotechnol., 1, 481 (1984)
• Seim, H. et al.: Appl. Microbiol. Biotechnol., 27, 538 (1984)