(2S)-2-amino-3-{[2-(benzyloxy)phenyl](3-fluorophenyl)methoxy}propanoic acid

• ChemBase ID: 153760
• Molecular Formular: C23H22FNO4
• Molecular Mass: 395.4234832
• Monoisotopic Mass: 395.15328641
• SMILES: c1ccc(cc1)COc1ccccc1C(c1cccc(c1)F)OC[C@@H](C(=O)O)N
• Canonical SMILES: Fc1cccc(c1)C(c1ccccc1OCc1ccccc1)OC[C@@H](C(=O)O)N
• InChI: InChI=1S/C23H22FNO4/c24-18-10-6-9-17(13-18)22(29-15-20(25)23(26)27)19-11-4-5-12-21(19)28-14-16-7-2-1-3-8-16/h1-13,20,22H,14-15,25H2,(H,26,27)/t20-,22?/m0/s1
• InChIKey: ADUSZEGHFWRTQS-AIBWNMTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-{[2-(benzyloxy)phenyl](3-fluorophenyl)methoxy}propanoic acid
• IUPAC Traditional name: (2S)-2-amino-3-{[2-(benzyloxy)phenyl](3-fluorophenyl)methoxy}propanoic acid
• Synonyms: O-[(2-Benzyloxyphenyl-3-flurophenyl)methyl]-L-serine; ALX-1393

Database IDs

• MDL Number: MFCD04974486
• PubChem SID: 24724393; 162247899
• PubChem CID: 16078939

CALCULATED PROPERTIES

• Acid pKa: 1.8662232
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.9736533
• LogD (pH = 7.4): 1.9586662
• Log P: 1.9736061
• Molar Refractivity: 106.9798 cm^3
• Polarizability: 41.770462 Å^3
• Polar Surface Area: 81.78 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble ~20 mg/mL
• Apperance: white powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: >98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C23H22NO4F

DETAILS

Sigma Aldrich - A5475

Biochem/physiol Actions
GlyT-2 glycine transporter inhibitor.
Application
ALX-1393 is a GlyT-2 glycine transporter inhibitor and GlyT2 may be a novel therapeutic target for the treatment of overactive bladder and/or bladder hypersensitive disorders such as bladder pain syndrome/interstitial cystitis.