N-(3-oxo-13-Phenyltridecanoyl)-L-homoserine Lactone

ID: ALA473010

PubChem CID: 25258815

Max Phase: Preclinical

Molecular Formula: C23H33NO4

Molecular Weight: 387.52

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3-oxo-13-phenyltridecanoyl-L-HSL | CHEMBL473010|3-oxo-13-phenyltridecanoyl-L-HSL

Canonical SMILES:  O=C(CCCCCCCCCCc1ccccc1)CC(=O)N[C@H]1CCOC1=O

Standard InChI:  InChI=1S/C23H33NO4/c25-20(18-22(26)24-21-16-17-28-23(21)27)15-11-6-4-2-1-3-5-8-12-19-13-9-7-10-14-19/h7,9-10,13-14,21H,1-6,8,11-12,15-18H2,(H,24,26)/t21-/m0/s1

Standard InChI Key:  ALYMHYDVCHESJL-NRFANRHFSA-N

Molfile:  

     RDKit          2D

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    6.9039  -21.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1039  -21.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0588  -22.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8309  -23.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3532  -22.3922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0428  -23.8317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417  -23.1417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6308  -22.7229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6381  -21.8979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9128  -23.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2020  -22.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4839  -23.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7731  -22.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0550  -23.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3442  -22.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3678  -23.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0801  -22.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7967  -23.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5091  -22.6681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2256  -23.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9380  -22.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6546  -23.0696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3662  -22.6559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0844  -23.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0880  -23.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3696  -24.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6564  -23.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2092  -21.8854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  3  7  1  1
 14 15  1  0
  2  3  1  0
 15 16  1  0
  7  8  1  0
 16 17  1  0
  3  4  1  0
 17 18  1  0
  8  9  2  0
 18 19  1  0
  4  5  1  0
 19 20  1  0
  8 10  1  0
 20 21  1  0
  5  1  1  0
 21 22  1  0
 10 11  1  0
 22 23  2  0
  1  2  1  0
 23 24  1  0
 11 12  1  0
 24 25  2  0
  4  6  2  0
 25 26  1  0
 12 13  1  0
 26 27  2  0
 27 22  1  0
 11 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA473010

   3-oxo-13-phenyltridecanoyl-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: 387.52

Molecular Weight (Monoisotopic): 387.2410

AlogP: 4.13

#Rotatable Bonds: 14

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: 10.37

CX Basic pKa: ┄

CX LogP: 4.97

CX LogD: 4.97

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.30

Np Likeness Score: 0.26

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