2-amino-6-hydroxyhexanoic acid

• ChemBase ID: 171017
• Molecular Formular: C6H13NO3
• Molecular Mass: 147.17232
• Monoisotopic Mass: 147.08954328
• SMILES: C(CCCCO)(N)C(=O)O
• Canonical SMILES: OCCCCC(C(=O)O)N
• InChI: InChI=1S/C6H13NO3/c7-5(6(9)10)3-1-2-4-8/h5,8H,1-4,7H2,(H,9,10)
• InChIKey: OLUWXTFAPJJWPL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-6-hydroxyhexanoic acid
• IUPAC Traditional name: 6-hydroxy-L-norleucine
• Synonyms: 6-Hydroxy-norleucine; (ε-Hydroxy-DL-norleucine; ε-Hydroxynorleucine; 6-Hydroxy-DL-norleucine; DL-ε-Hydroxynorleucine; Hexahomoserine; NSC 16535; NSC 32041; DL-6-Hydroxy Norleucine

Database IDs

• CAS Number: 305-77-1
• PubChem SID: 164226927
• PubChem CID: 233487

CALCULATED PROPERTIES

• Acid pKa: 2.4582765
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.866048
• LogD (pH = 7.4): -2.8687441
• Log P: -2.8659077
• Molar Refractivity: 36.152 cm^3
• Polarizability: 14.5027485 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H948855

An intermediate for antiviral and antihypertensive drugs.

REFERENCES

• Kaufman, S., et al.: J. Biol. Chem., 257, 14667 (1982)
• Hanson, R., et al.: Bioorg. Chem., 18, 116 (1982)
• Oshima, T., et al.: J. Bacteriol., 173, 3943 (1982)
• Oshima, T., et al.: Eur. J. Biochem., 222, 305 (1982)
• Robl, J., et al.: J. Med. Chem., 40, 157