(2S,3R)-3-hydroxy-2-(methylamino)butanoic acid

• ChemBase ID: 154618
• Molecular Formular: C5H11NO3
• Molecular Mass: 133.14574
• Monoisotopic Mass: 133.07389322
• SMILES: C[C@H]([C@@H](C(=O)O)NC)O
• Canonical SMILES: CN[C@H](C(=O)O)[C@H](O)C
• InChI: InChI=1S/C5H11NO3/c1-3(7)4(6-2)5(8)9/h3-4,6-7H,1-2H3,(H,8,9)/t3-,4+/m1/s1
• InChIKey: CCAIIPMIAFGKSI-DMTCNVIQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-3-hydroxy-2-(methylamino)butanoic acid
• IUPAC Traditional name: (2S,3R)-3-hydroxy-2-(methylamino)butanoic acid
• Synonyms: (2S,3R)-3-Hydroxy-2-(methylamino)butyric acid; N-Me-Thr-OH; N-Methyl-L-threonine

Database IDs

• CAS Number: 2812-28-4
• MDL Number: MFCD02094308
• Beilstein Number: 1722279
• PubChem SID: 162248756
• PubChem CID: 7010355

CALCULATED PROPERTIES

• Acid pKa: 1.8921934
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.2477891
• LogD (pH = 7.4): -3.2487621
• Log P: -3.2477574
• Molar Refractivity: 31.2344 cm^3
• Polarizability: 12.682326 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 -24.0±1.0°, c = 1 in 1 M HCl

Safety Information

• German water hazard class: 3
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (TLC)
• Compostion: carbon, 44.2-46.0%; nitrogen, 10.3-10.8%
• Empirical Formula (Hill Notation): C5H11NO3

DETAILS

Sigma Aldrich - 55345

Biochem/physiol Actions
N-Methyl amino acids play an important role in investigations on prevention or therapy of Alzheimer′s disease1, neurofibrillary tangles or amyloid plaque are physiological characteristics of this disease and ?-amyloid(40) fibrillogenesis and disassembly of ?-amyloid(40) fibrils is inhibited by short ?-amyloid congeners containing N-methyl amino acids at alternate residue.