(2S)-2-amino-6-hydroxyhexanoic acid

• ChemBase ID: 3091
• Molecular Formular: C6H13NO3
• Molecular Mass: 147.17232
• Monoisotopic Mass: 147.08954328
• SMILES: N[C@@H](CCCCO)C(=O)O
• Canonical SMILES: OCCCC[C@@H](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)/t5-/m0/s1
• InChIKey: OLUWXTFAPJJWPL-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-6-hydroxyhexanoic acid
• IUPAC Traditional name: 6-hydroxy-L-norleucine
• Synonyms: 6-Hydroxy-L-Norleucine; 6-Hydroxy-L-norleucine; (+)-L-ε-Hydroxynorleucine; (S)-2-Amino-6-hydroxyhexanoic Acid; L-α-Amino-ε-hydroxy-n-caproic Acid; L-ε-Hydroxynorleucine; L-Hexahomoserine; NSC 206290; L-6-Hydroxy Norleucine

Database IDs

• CAS Number: 6033-32-5
• PubChem SID: 46508093; 160966535
• PubChem CID: 97725

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: -2.94
• LOG S: -0.16
• Solubility (Water): 1.01e+02 g/l

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White Solid
• Melting Point: 238-241°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

DrugBank - DB03412

Drug information: experimental

Toronto Research Chemicals - H948858

A key chiral intermediate used for synthesis of a vasopeptidase inhibitor.

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