(2R,3S)-2-amino-3-hydroxy-4-methylpentanoic acid

• ChemBase ID: 170697
• Molecular Formular: C6H13NO3
• Molecular Mass: 147.17232
• Monoisotopic Mass: 147.08954328
• SMILES: [C@H]([C@H](C(C)C)O)(N)C(=O)O
• Canonical SMILES: CC([C@@H]([C@H](C(=O)O)N)O)C
• InChI: InChI=1S/C6H13NO3/c1-3(2)5(8)4(7)6(9)10/h3-5,8H,7H2,1-2H3,(H,9,10)/t4-,5+/m1/s1
• InChIKey: ZAYJDMWJYCTABM-UHNVWZDZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-2-amino-3-hydroxy-4-methylpentanoic acid
• IUPAC Traditional name: (2R,3S)-2-amino-3-hydroxy-4-methylpentanoic acid
• Synonyms: threo-3-Hydroxy-D-leucine; (2R,3S)-2-Amino-3-hydroxy-4-methylpentanoic acid; D-threo-β-Hydroxyleucine; (3S)-3-Hydroxy-D-leucine; (2R,3S)-β-Hydroxyleucine

Database IDs

• CAS Number: 87421-23-6
• PubChem SID: 164226607
• PubChem CID: 2724869

CALCULATED PROPERTIES

• Acid pKa: 2.440832
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.5825717
• LogD (pH = 7.4): -2.5926387
• Log P: -2.5826461
• Molar Refractivity: 35.4554 cm^3
• Polarizability: 14.5027485 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H943740

(2R,3S)-β-Hydroxyleucine is a nonprotein amino acid. (2R,3S)-β-Hydroxyleucineis an inhibitor of serine protease. In particular, (2R,3S)-β-Hydroxyleucine was effective in inhibiting trypsin and proteinase K of the serine proteases group. (2R,3S)-β-Hydroxyl

REFERENCES

• Hovhannisyan, N. et al.: Amino Acids, 37, 531 (2009)
• Chitchyan, M.B. et al.: Hayas. Kensab. Hand., 59, 248 (2009)