rac-1-(4-chlorophenoxy)-3-imidazol-1-yl-propan-2-ol

ID: ALA4760487

PubChem CID: 2916479

Max Phase: Preclinical

Molecular Formula: C12H13ClN2O2

Molecular Weight: 252.70

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  OC(COc1ccc(Cl)cc1)Cn1ccnc1

Standard InChI:  InChI=1S/C12H13ClN2O2/c13-10-1-3-12(4-2-10)17-8-11(16)7-15-6-5-14-9-15/h1-6,9,11,16H,7-8H2

Standard InChI Key:  SWHUSRDGLBXQJC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
    1.6742  -20.4504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6731  -21.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3811  -21.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0908  -21.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0880  -20.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3793  -20.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651  -21.6780    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7941  -20.0355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5034  -20.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2095  -20.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9188  -20.4361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2065  -19.2130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6249  -20.0249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3736  -20.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9181  -19.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5068  -19.0348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7082  -19.2078    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  6  2  0
  6  1  1  0
  2  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4760487

   1-[3'-(4'-Chlorophenoxy)-2'-hydroxypropyl]imidazole

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: 252.70

Molecular Weight (Monoisotopic): 252.0666

AlogP: 1.98

#Rotatable Bonds: 5

Polar Surface Area: 47.28

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.97

CX Basic pKa: 6.48

CX LogP: 1.70

CX LogD: 1.66

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.89

Np Likeness Score: -1.49

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