N-4-Phenylbutanoyl-L-homoserine Lactone

ID: ALA448002

PubChem CID: 11550533

Max Phase: Preclinical

Molecular Formula: C14H17NO3

Molecular Weight: 247.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCCc1ccccc1)N[C@H]1CCOC1=O

Standard InChI:  InChI=1S/C14H17NO3/c16-13(15-12-9-10-18-14(12)17)8-4-7-11-5-2-1-3-6-11/h1-3,5-6,12H,4,7-10H2,(H,15,16)/t12-/m0/s1

Standard InChI Key:  FBUYEVACKSZURO-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    1.4289   -1.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6289   -1.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5838   -2.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3559   -2.4844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8782   -1.8422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5678   -3.2817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -2.5917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8442   -2.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8369   -1.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5622   -2.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2730   -2.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9911   -2.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7019   -2.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6938   -1.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4038   -0.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1229   -1.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1275   -2.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4169   -2.5556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
  4  5  1  0
  8 10  1  0
  5  1  1  0
 10 11  1  0
  1  2  1  0
 11 12  1  0
  4  6  2  0
 12 13  1  0
 13 14  2  0
  3  7  1  1
 14 15  1  0
  2  3  1  0
 15 16  2  0
  7  8  1  0
 16 17  1  0
  3  4  1  0
 17 18  2  0
 18 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA448002

   N-[(3S)-2-oxooxolan-3-yl]-4-phenylbutanamide

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: 247.29

Molecular Weight (Monoisotopic): 247.1208

AlogP: 1.44

#Rotatable Bonds: 5

Polar Surface Area: 55.40

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.52

CX Basic pKa: ┄

CX LogP: 1.64

CX LogD: 1.64

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.80

Np Likeness Score: -0.39

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. 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