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

ID: ALA2392447

PubChem CID: 71655083

Max Phase: Preclinical

Molecular Formula: C19H15ClN2O3

Molecular Weight: 354.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCc1cc(-c2ccc(Oc3ccc(C#N)cc3O)c(Cl)c2)no1

Standard InChI:  InChI=1S/C19H15ClN2O3/c1-2-3-14-10-16(22-25-14)13-5-7-18(15(20)9-13)24-19-6-4-12(11-21)8-17(19)23/h4-10,23H,2-3H2,1H3

Standard InChI Key:  AGPRFNDYMUEREM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   16.0703   -1.5322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7866   -1.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3668   -1.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4817   -1.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6588   -1.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1897   -1.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9554   -1.9611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3715   -2.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7912   -2.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9600   -2.7782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2068   -2.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4729   -0.6946    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.6500   -0.7231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6681   -3.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4992   -3.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2544   -3.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5488   -3.6074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8672   -3.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8700   -4.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6470   -4.2845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1280   -3.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6483   -2.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9452   -3.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3531   -4.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1703   -4.3337    0.0000 C   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:

   

   ALA2392447

   4-[2-Chloro-4-(5-propyl-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: 354.79

Molecular Weight (Monoisotopic): 354.0771

AlogP: 5.32

#Rotatable Bonds: 5

Polar Surface Area: 79.28

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.33

CX Basic pKa: 0.62

CX LogP: 5.19

CX LogD: 4.86

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.67

Np Likeness Score: -1.03

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