(2S,4S)-4-hydroxy-1-methylpyrrolidine-2-carboxylic acid

• ChemBase ID: 154630
• Molecular Formular: C6H11NO3
• Molecular Mass: 145.15644
• Monoisotopic Mass: 145.07389322
• SMILES: CN1C[C@H](C[C@H]1C(=O)O)O
• Canonical SMILES: O[C@@H]1CN([C@@H](C1)C(=O)O)C
• InChI: InChI=1S/C6H11NO3/c1-7-3-4(8)2-5(7)6(9)10/h4-5,8H,2-3H2,1H3,(H,9,10)/t4-,5-/m0/s1
• InChIKey: FMIPNAUMSPFTHK-WHFBIAKZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S)-4-hydroxy-1-methylpyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2S,4S)-4-hydroxy-1-methylpyrrolidine-2-carboxylic acid
• Synonyms: N-Me-cis-Hyp-OH; (4S)-4-Hydroxy-1-methyl-L-proline; N-Methyl-L-allohydroxyproline; N-Methyl-cis-4-hydroxy-L-proline; (4S)-4-羟基-1-甲基-L-脯氨酸; N-甲基-L-别羟脯氨酸; N-甲基-顺-4-羟基-L-脯氨酸

Database IDs

• CAS Number: 67463-44-9
• MDL Number: MFCD02094307
• PubChem SID: 162248768
• PubChem CID: 9860390

CALCULATED PROPERTIES

• Acid pKa: 1.4843092
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.5919702
• LogD (pH = 7.4): -3.5938387
• Log P: -3.5919988
• Molar Refractivity: 34.6769 cm^3
• Polarizability: 13.797867 Å^3
• Polar Surface Area: 60.77 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D -68.5±2.5°, c = 1 in H2O

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36-43
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317-H319
• GHS Precautionary statements: P280-P305 + P351 + P338

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C6H11NO3

DETAILS

Sigma Aldrich - 80351

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.