(8S)-8-amino-7-oxononanoic acid

• ChemBase ID: 160363
• Molecular Formular: C9H17NO3
• Molecular Mass: 187.23618
• Monoisotopic Mass: 187.12084341
• SMILES: C[C@@H](C(=O)CCCCCC(=O)O)N
• Canonical SMILES: OC(=O)CCCCCC(=O)[C@@H](N)C
• InChI: InChI=1S/C9H17NO3/c1-7(10)8(11)5-3-2-4-6-9(12)13/h7H,2-6,10H2,1H3,(H,12,13)/t7-/m0/s1
• InChIKey: GUAHPAJOXVYFON-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8S)-8-amino-7-oxononanoic acid
• IUPAC Traditional name: (8S)-8-amino-7-oxononanoic acid
• Synonyms: AOP; (8S)-8-Amino-7-oxo-nonanoic Acid Hydrochloride; 8-Amino-7-oxopelargonic Acid Hydrochloride

Database IDs

• CAS Number: 177408-65-0
• PubChem SID: 162254498
• PubChem CID: 448124

CALCULATED PROPERTIES

• Acid pKa: 4.4482427
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.3667789
• LogD (pH = 7.4): -1.4128585
• Log P: -1.3484309
• Molar Refractivity: 48.7447 cm^3
• Polarizability: 19.447386 Å^3
• Polar Surface Area: 80.39 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 134-136°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A618750

An intermediate in the synthesis of biotin. Pimeloyl-CoA is transformed into AOP in the presence of L-alanine by the enzyme AOP synthase. The catalytic mechanism of AOP synthase has been studied for the elucidation of inhibitors as potential antimicrobia

REFERENCES

• Ohsugi, M., et al.: J. Nutr. Sci. Vitaminol., 34 (4)
• 343 (4)
• Pearson, B.M., et al.: Lett. Appl. Microbiol., 10 (4)
• 89 (4)
• Ploux, O., et al.: Biochem. J., 283, 327 (1992)