N-12-Phenyldodecanoyl-L-homoserine Lactone

ID: ALA474581

PubChem CID: 25258814

Max Phase: Preclinical

Molecular Formula: C22H33NO3

Molecular Weight: 359.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCCCCCCCCCCc1ccccc1)N[C@H]1CCOC1=O

Standard InChI:  InChI=1S/C22H33NO3/c24-21(23-20-17-18-26-22(20)25)16-12-7-5-3-1-2-4-6-9-13-19-14-10-8-11-15-19/h8,10-11,14-15,20H,1-7,9,12-13,16-18H2,(H,23,24)/t20-/m0/s1

Standard InChI Key:  BGOVUZZHXJQMFB-FQEVSTJZSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   18.8789  -18.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0789  -18.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0338  -19.6943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8059  -19.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3282  -19.3505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0178  -20.7900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3167  -20.1000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6058  -19.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6131  -18.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8878  -20.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1770  -19.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4589  -20.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7481  -19.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0300  -20.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3192  -19.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6072  -20.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8949  -19.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1783  -20.0425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4659  -19.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7494  -20.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0370  -19.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0435  -18.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3320  -18.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6145  -18.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6129  -19.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3250  -20.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  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  2  0
 10 11  1  0
 22 23  1  0
  1  2  1  0
 23 24  2  0
 11 12  1  0
 24 25  1  0
  4  6  2  0
 25 26  2  0
 26 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA474581

   N-[(3S)-2-oxooxolan-3-yl]-12-phenyldodecanamide

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: 359.51

Molecular Weight (Monoisotopic): 359.2460

AlogP: 4.56

#Rotatable Bonds: 13

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: 12.61

CX Basic pKa: ┄

CX LogP: 5.20

CX LogD: 5.20

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.41

Np Likeness Score: -0.14

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. Lowery CA, Salzameda NT, Sawada D, Kaufmann GF, Janda KD..  (2010)  Medicinal chemistry as a conduit for the modulation of quorum sensing.,  53  (21): [PMID:20669927] [10.1021/jm901742e]

Source

Source(1):

• Scientific Literature