4-{2-Chloro-4-[5-(2-hydroxyethyl)-1,2-oxazol-3-yl]phenoxy}-3-hydroxybenzonitrile

ID: ALA2392448

PubChem CID: 71655084

Max Phase: Preclinical

Molecular Formula: C18H13ClN2O4

Molecular Weight: 356.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(Oc2ccc(-c3cc(CCO)on3)cc2Cl)c(O)c1

Standard InChI:  InChI=1S/C18H13ClN2O4/c19-14-8-12(15-9-13(5-6-22)25-21-15)2-4-17(14)24-18-3-1-11(10-20)7-16(18)23/h1-4,7-9,22-23H,5-6H2

Standard InChI Key:  XKGPTRKBPOKEDN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   28.2332   -1.8913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9495   -2.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5298   -2.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6446   -1.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8217   -1.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3527   -2.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1183   -2.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5345   -3.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9541   -3.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1230   -3.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3697   -3.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6358   -1.0537    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   26.8129   -1.0821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8310   -3.5419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6622   -3.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4173   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7117   -3.9664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.0302   -3.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0330   -4.3902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.8099   -4.6436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.2910   -3.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8113   -3.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1082   -3.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5161   -4.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3332   -4.6927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  2  0
  6  4  2  0
  7  5  1  0
  8  3  1  0
  9  2  2  0
 10 14  1  0
 11 15  2  0
 12  4  1  0
 13  5  1  0
 14  8  2  0
 15  9  1  0
  7 10  2  0
  6 11  1  0
 16 17  3  0
 10 16  1  0
 11 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 18  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2392448

   4-[2-Chloro-4-[5-(2-hydroxyethyl)-1,2-oxazol-3-yl]phenoxy]-3-hydroxybenzonitrile

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: 356.77

Molecular Weight (Monoisotopic): 356.0564

AlogP: 3.90

#Rotatable Bonds: 5

Polar Surface Area: 99.51

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.33

CX Basic pKa: 0.46

CX LogP: 3.24

CX LogD: 2.91

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.72

Np Likeness Score: -0.95

References

1. Muench SP, Stec J, Zhou Y, Afanador GA, McPhillie MJ, Hickman MR, Lee PJ, Leed SE, Auschwitz JM, Prigge ST, Rice DW, McLeod R..  (2013)  Development of a triclosan scaffold which allows for adaptations on both the A- and B-ring for transport peptides.,  23  (12): [PMID:23664871] [10.1016/j.bmcl.2013.04.035]

Source

Source(1):

• Scientific Literature