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

ID: ALA473462

PubChem CID: 10354586

Max Phase: Preclinical

Molecular Formula: C13H13NO4

Molecular Weight: 247.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CC(=O)c1ccccc1)N[C@H]1CCOC1=O

Standard InChI:  InChI=1S/C13H13NO4/c15-11(9-4-2-1-3-5-9)8-12(16)14-10-6-7-18-13(10)17/h1-5,10H,6-8H2,(H,14,16)/t10-/m0/s1

Standard InChI Key:  ZZCWQSYPMQTLRO-JTQLQIEISA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   17.2164    3.3655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4164    3.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3713    2.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1434    2.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6657    2.6703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3553    1.2308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6542    1.9208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9433    2.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9506    3.1646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2253    1.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5145    2.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7964    1.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0899    2.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3723    1.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3646    1.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0804    0.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7951    1.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5217    3.1771    0.0000 O   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  2  0
 13 14  1  0
  3  7  1  1
 14 15  2  0
  2  3  1  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
 17 12  1  0
  3  4  1  0
 11 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA473462

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

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: 247.25

Molecular Weight (Monoisotopic): 247.0845

AlogP: 0.69

#Rotatable Bonds: 4

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: 11.36

CX Basic pKa: ┄

CX LogP: 0.56

CX LogD: 0.56

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.48

Np Likeness Score: -0.25

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]

Source

Source(1):

• Scientific Literature