(2S,3R)-2-[(2S)-2-amino-4-[(3S)-3-hydroxy-2-oxoazetidin-3-yl]butanamido]-3-hydroxybutanoic acid

• ChemBase ID: 129686
• Molecular Formular: C11H19N3O6
• Molecular Mass: 289.28506
• Monoisotopic Mass: 289.12738534
• SMILES: O=C(O)[C@@H](NC(=O)[C@@H](N)CC[C@@]1(O)C(=O)NC1)[C@H](O)C
• Canonical SMILES: O=C([C@H](CC[C@]1(O)CNC1=O)N)N[C@H](C(=O)O)[C@H](O)C
• InChI: InChI=1S/C11H19N3O6/c1-5(15)7(9(17)18)14-8(16)6(12)2-3-11(20)4-13-10(11)19/h5-7,15,20H,2-4,12H2,1H3,(H,13,19)(H,14,16)(H,17,18)/t5-,6+,7+,11+/m1/s1
• InChIKey: BFSBNVPBVGFFCF-WDOVLDDZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-[(2S)-2-amino-4-[(3S)-3-hydroxy-2-oxoazetidin-3-yl]butanamido]-3-hydroxybutanoic acid
• IUPAC Traditional name: tabtoxin
• Synonyms: N-[(2S)-2-Amino-4-[(3S)-3-hydroxy-2-oxo-3-azetidinyl]-1-oxobutyl]-L-threonine; (S)-γ-(3-Hydroxy-2-oxo-3-azetidinyl)-L-α-aminobutyryl-L-threonine; Tabtoxin

Database IDs

• CAS Number: 40957-90-2
• PubChem SID: 162223975
• PubChem CID: 107817
• Chemspider ID: 96964
• Wikipedia Title: Tabtoxin

CALCULATED PROPERTIES

• Acid pKa: 3.316105
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -5.468479
• LogD (pH = 7.4): -5.5912995
• Log P: -5.4709253
• Molar Refractivity: 65.3554 cm^3
• Polarizability: 26.224691 Å^3
• Polar Surface Area: 161.98 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false