N-(3-oxo-4-Phenylbutanoyl)-L-homoserine Lactone

ID: ALA473592

Chembl Id: CHEMBL473592

Cas Number: 202284-86-4

PubChem CID: 11536248

Max Phase: Preclinical

Molecular Formula: C14H15NO4

Molecular Weight: 261.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CC(=O)N[C@H]1CCOC1=O)Cc1ccccc1

Standard InChI:  InChI=1S/C14H15NO4/c16-11(8-10-4-2-1-3-5-10)9-13(17)15-12-6-7-19-14(12)18/h1-5,12H,6-9H2,(H,15,17)/t12-/m0/s1

Standard InChI Key:  SZKJWOMSLREKNK-LBPRGKRZSA-N

Alternative Forms

1. Parent:

   

   ALA473592

   N-(3-oxo-3-Phenylpropanoyl)-L-homoserine Lactone

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 261.28

Molecular Weight (Monoisotopic): 261.1001

AlogP: 0.62

#Rotatable Bonds: 5

Polar Surface Area: 72.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.30

CX Basic pKa: ┄

CX LogP: 0.97

CX LogD: 0.97

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.62

Np Likeness Score: -0.09

References

1. Oliver CM, Schaefer AL, Greenberg EP, Sufrin JR..  (2009)  Microwave synthesis and evaluation of phenacylhomoserine lactones as anticancer compounds that minimally activate quorum sensing pathways in Pseudomonas aeruginosa.,  52  (6): [PMID:19260689] [10.1021/jm8015377]

2. Ahumedo M, Díaz A, Vivas-Reyes R..  (2010)  Theoretical and structural analysis of the active site of the transcriptional regulators LasR and TraR, using molecular docking methodology for identifying potential analogues of acyl homoserine lactones (AHLs) with anti-quorum sensing activity.,  45  (2): [PMID:19945196] [10.1016/j.ejmech.2009.11.004]

3. Lowery CA, Salzameda NT, Sawada D, Kaufmann GF, Janda KD..  (2010)  Medicinal chemistry as a conduit for the modulation of quorum sensing.,  53  (21): [PMID:20669927] [10.1021/jm901742e]

4. Chbib C..  (2020)  Impact of the structure-activity relationship of AHL analogues on quorum sensing in Gram-negative bacteria.,  28  (3): [PMID:31918952] [10.1016/j.bmc.2019.115282]

Source

Source(1):

• Scientific Literature