rac-1-[1-[2-[4-(2-Phenylethynyl)phenyl]ethyl]imidazol-2-yl]ethanol

ID: ALA4759498

PubChem CID: 142479818

Max Phase: Preclinical

Molecular Formula: C21H20N2O

Molecular Weight: 316.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(O)c1nccn1CCc1ccc(C#Cc2ccccc2)cc1

Standard InChI:  InChI=1S/C21H20N2O/c1-17(24)21-22-14-16-23(21)15-13-20-11-9-19(10-12-20)8-7-18-5-3-2-4-6-18/h2-6,9-12,14,16-17,24H,13,15H2,1H3

Standard InChI Key:  XMPAWNVELJQJNW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   34.1363   -4.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9535   -4.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2078   -3.6229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5449   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8861   -3.6229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5436   -2.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2507   -1.9140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8353   -1.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1088   -3.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5018   -3.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7245   -3.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5594   -2.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7829   -2.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1749   -3.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3486   -3.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1249   -4.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3983   -2.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6156   -2.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8371   -2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6665   -1.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8889   -1.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2834   -1.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4607   -2.7195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2381   -2.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 14 17  1  0
 17 18  3  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4759498

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 316.40

Molecular Weight (Monoisotopic): 316.1576

AlogP: 3.58

#Rotatable Bonds: 4

Polar Surface Area: 38.05

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.83

CX Basic pKa: 5.44

CX LogP: 4.09

CX LogD: 4.08

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.75

Np Likeness Score: -0.87

References

1. Yamada Y,Takashima H,Walmsley DL,Ushiyama F,Matsuda Y,Kanazawa H,Yamaguchi-Sasaki T,Tanaka-Yamamoto N,Yamagishi J,Kurimoto-Tsuruta R,Ogata Y,Ohtake N,Angove H,Baker L,Harris R,Macias A,Robertson A,Surgenor A,Watanabe H,Nakano K,Mima M,Iwamoto K,Okada A,Takata I,Hitaka K,Tanaka A,Fujita K,Sugiyama H,Hubbard RE.  (2020)  Fragment-Based Discovery of Novel Non-Hydroxamate LpxC Inhibitors with Antibacterial Activity.,  63  (23): [PMID:33210531] [10.1021/acs.jmedchem.0c01215]

Source

Source(1):

• Scientific Literature