N-3-Phenylpropanoyl-L-homoserine Lactone

ID: ALA473785

PubChem CID: 22879127

Max Phase: Preclinical

Molecular Formula: C13H15NO3

Molecular Weight: 233.27

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3-pherylpropanoyl-L-HSL | CHEMBL473785|3-pherylpropanoyl-L-HSL|SCHEMBL8735482|BDBM50416512

Canonical SMILES:  O=C(CCc1ccccc1)N[C@H]1CCOC1=O

Standard InChI:  InChI=1S/C13H15NO3/c15-12(14-11-8-9-17-13(11)16)7-6-10-4-2-1-3-5-10/h1-5,11H,6-9H2,(H,14,15)/t11-/m0/s1

Standard InChI Key:  RUQJSJHHSDXJNE-NSHDSACASA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
    7.8581    3.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0581    3.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0129    2.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7851    1.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3073    2.5495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9969    1.1100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2958    1.8000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5850    2.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5922    3.0437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8669    1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1561    2.2313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4381    1.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7315    2.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0140    1.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0063    1.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7221    0.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4368    1.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA473785

   3-pherylpropanoyl-L-HSL

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: 233.27

Molecular Weight (Monoisotopic): 233.1052

AlogP: 1.05

#Rotatable Bonds: 4

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: 12.45

CX Basic pKa: ┄

CX LogP: 1.20

CX LogD: 1.20

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.79

Np Likeness Score: -0.43

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. Solorzano C, Antonietti F, Duranti A, Tontini A, Rivara S, Lodola A, Vacondio F, Tarzia G, Piomelli D, Mor M..  (2010)  Synthesis and structure-activity relationships of N-(2-oxo-3-oxetanyl)amides as N-acylethanolamine-hydrolyzing acid amidase inhibitors.,  53  (15): [PMID:20604568] [10.1021/jm100582w]

Source

Source(1):

• Scientific Literature