N-(3-oxo-6-Phenylhexanoyl)-L-homoserine Lactone

ID: ALA473594

PubChem CID: 25258817

Max Phase: Preclinical

Molecular Formula: C16H19NO4

Molecular Weight: 289.33

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H19NO4/c18-13(8-4-7-12-5-2-1-3-6-12)11-15(19)17-14-9-10-21-16(14)20/h1-3,5-6,14H,4,7-11H2,(H,17,19)/t14-/m0/s1

Standard InChI Key:  IGINZWZGJGMEBS-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   21.9997   -4.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1997   -4.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1546   -5.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9268   -5.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4490   -5.0255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1386   -6.4650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4375   -5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7267   -5.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7339   -4.5313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0086   -5.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2978   -5.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5797   -5.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8689   -5.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1508   -5.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4400   -5.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4525   -4.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7426   -4.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0235   -4.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0189   -5.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7295   -5.7264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3050   -4.5187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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  1  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
  8  9  2  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
 20 15  1  0
  8 10  1  0
 11 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA473594

   3-oxo-N-[(3S)-2-oxooxolan-3-yl]-6-phenylhexanamide

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: 289.33

Molecular Weight (Monoisotopic): 289.1314

AlogP: 1.40

#Rotatable Bonds: 7

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: 10.77

CX Basic pKa: ┄

CX LogP: 1.86

CX LogD: 1.86

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.61

Np Likeness Score: 0.18

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. Murray EJ, Crowley RC, Truman A, Clarke SR, Cottam JA, Jadhav GP, Steele VR, O'Shea P, Lindholm C, Cockayne A, Chhabra SR, Chan WC, Williams P..  (2014)  Targeting Staphylococcus aureus quorum sensing with nonpeptidic small molecule inhibitors.,  57  (6): [PMID:24592914] [10.1021/jm500215s]

Source

Source(1):

• Scientific Literature