(5S)-3-acetyl-5-[(2S)-butan-2-yl]-4-hydroxy-2,5-dihydro-1H-pyrrol-2-one

• ChemBase ID: 178158
• Molecular Formular: C10H15NO3
• Molecular Mass: 197.231
• Monoisotopic Mass: 197.10519335
• SMILES: C1(=O)C(=C([C@@H](N1)[C@H](CC)C)O)C(=O)C
• Canonical SMILES: CC[C@@H]([C@@H]1NC(=O)C(=C1O)C(=O)C)C
• InChI: InChI=1S/C10H15NO3/c1-4-5(2)8-9(13)7(6(3)12)10(14)11-8/h5,8,13H,4H2,1-3H3,(H,11,14)/t5-,8-/m0/s1
• InChIKey: CEIZFXOZIQNICU-XNCJUZBTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-3-acetyl-5-[(2S)-butan-2-yl]-4-hydroxy-2,5-dihydro-1H-pyrrol-2-one
• IUPAC Traditional name: (5S)-3-acetyl-5-[(2S)-butan-2-yl]-4-hydroxy-1,5-dihydropyrrol-2-one
• Synonyms: L-3-Acetyl-5-sec-butyl-4-hydroxy-3-pyrrolin-2-one; (5S)-3-Acetyl-1,5-dihydro-4-hydroxy-5-[(1S)-1-methylpropyl]-2H-pyrrol-2-one; AAC-toxin; L-Tenuazonic Acid; Tenuazonic Acid

Database IDs

• CAS Number: 610-88-8
• PubChem SID: 164234068
• PubChem CID: 54683011

CALCULATED PROPERTIES

• Acid pKa: 2.8067589
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.2155385
• LogD (pH = 7.4): -2.936391
• Log P: 0.56878227
• Molar Refractivity: 52.7303 cm^3
• Polarizability: 20.11531 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T019620

An alternaria mycotoxin, found in common edible crops. It inhibits protein synthesis in fibroblasts.

REFERENCES

• Andersen, B., et al.: Int. J. Food Microbiol., 111, 105 (2006)
• Liu, Y., et al.: J. Agric. Food Chem., 55, 5180 (2006)
• Aly, A., et al.: J. Nat. Prod., 71, 972 (2006)