Name: Ambuic acid
Rating: 5 (10 reviews)

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HIT ID:HIT212038716
Cas No:340774-69-8
常用名:Ambuic acid
IUPAC:(2E)-4-[(1R,5R,6R)-3-[(1E)-hept-1-en-1-yl]-5-hydroxy-4-(hydroxymethyl)-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-2-methylbut-2-enoic acid
IUPAC:(2E)-4-[(1R,5R,6R)-3-[(1E)-hept-1-en-1-yl]-5-hydroxy-4-(hydroxymethyl)-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-2-methylbut-2-enoic acid
InChI key:UDSQZJMGPSRCEM-HDKVZZTHSA-N

分子式:C19H26O6
分子量:350.411
氢键供体数 (HBD):3
氢键受体数 (HBA):6
LogP:2.3639445
SMILES:CCCCC\C=C\C1=C(CO)[C@@H](O)[C@H]2O[C@@]2(C\C=C(/C)C(O)=O)C1=O |c:7|
SMILES:CCCCC\C=C\C1=C(CO)[C@@H](O)[C@H]2O[C@@]2(C\C=C(/C)C(O)=O)C1=O |c:7|

Ambuic acid is a cyclohexanone that has phytopathogenic antifungal, quorum sensing inhibitory, and antibacterial activities. Ambuic acid inhibits the biosynthesis of cyclic peptides involved in quorum sensing, including gelatinase biosynthesis-activating pheromone (GBAP) in E. faecalis, autoinducing peptide I (AIP-I) in S. aureus, and LsrD698 and LsrD826 in L. innocua. It suppresses abcess formation in a mouse model of skin infection induced by methicillin-resistant S. aureus (MRSA) when administered at a dose of 5 µg and decreases the activity of the agr quorum sensing system in an in vivo reporter assay.

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