(2S)-3-hydroxy-2-(methylamino)propanoic acid

• ChemBase ID: 154619
• Molecular Formular: C4H9NO3
• Molecular Mass: 119.11916
• Monoisotopic Mass: 119.05824315
• SMILES: CN[C@@H](CO)C(=O)O
• Canonical SMILES: CN[C@H](C(=O)O)CO
• InChI: InChI=1S/C4H9NO3/c1-5-3(2-6)4(7)8/h3,5-6H,2H2,1H3,(H,7,8)/t3-/m0/s1
• InChIKey: PSFABYLDRXJYID-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-hydroxy-2-(methylamino)propanoic acid
• IUPAC Traditional name: (2S)-3-hydroxy-2-(methylamino)propanoic acid
• Synonyms: (S)-3-Hydroxy-2-(methylamino)propionic acid; N-Me-Ser-OH; N-Methyl-L-serine

Database IDs

• CAS Number: 2480-26-4
• MDL Number: MFCD00037756
• Beilstein Number: 2498641
• PubChem SID: 162248757
• PubChem CID: 7009640

CALCULATED PROPERTIES

• Acid pKa: 1.7578363
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.6643322
• LogD (pH = 7.4): -3.6657603
• Log P: -3.6643286
• Molar Refractivity: 26.8156 cm^3
• Polarizability: 10.868561 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D +9.5±1.0°, c = 1 in 1 M HCl

Safety Information

• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338

Product Information

• Purity: ≥98% (TLC)
• Compostion: carbon, 39.5-41.1%; nitrogen, 11.5-12.0%
• Empirical Formula (Hill Notation): C4H9NO3

DETAILS

Sigma Aldrich - 73156

Biochem/physiol Actions
N-Methyl-L-serine has been found to stimulate production of high molecular mass hyaluronan in human fibroblasts. This effect was specific to methylated L-serine and not observed with other methylated amino acids. 1