5-(4-[(3-Methylbut-2-en-1-yl)oxy]phenyl)-2-phenyloxazole

ID: ALA4090016

PubChem CID: 137644688

Max Phase: Preclinical

Molecular Formula: C20H19NO2

Molecular Weight: 305.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=CCOc1ccc(-c2cnc(-c3ccccc3)o2)cc1

Standard InChI:  InChI=1S/C20H19NO2/c1-15(2)12-13-22-18-10-8-16(9-11-18)19-14-21-20(23-19)17-6-4-3-5-7-17/h3-12,14H,13H2,1-2H3

Standard InChI Key:  UEZFSEDRMLVNJT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    7.1539   -6.1202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6976   -5.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2890   -4.8047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4906   -4.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4066   -5.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5121   -5.5978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8465   -6.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6569   -6.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1371   -5.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8068   -5.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9923   -4.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6975   -6.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925   -5.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2834   -6.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2834   -7.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925   -7.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6975   -7.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5743   -7.4243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8653   -7.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8653   -6.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1603   -5.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1603   -4.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4512   -6.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  6 11  2  0
  2  6  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 18 19  1  0
 15 18  1  0
  5 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4090016

   ---

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: 305.38

Molecular Weight (Monoisotopic): 305.1416

AlogP: 5.35

#Rotatable Bonds: 5

Polar Surface Area: 35.26

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 0.68

CX LogP: 4.71

CX LogD: 4.71

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.60

Np Likeness Score: -0.24

References

1. Robles AJ, McCowen S, Cai S, Glassman M, Ruiz F, Cichewicz RH, McHardy SF, Mooberry SL..  (2017)  Structure-Activity Relationships of New Natural Product-Based Diaryloxazoles with Selective Activity against Androgen Receptor-Positive Breast Cancer Cells.,  60  (22): [PMID:29053266] [10.1021/acs.jmedchem.7b01228]

2. Robles AJ, McCowen S, Cai S, Glassman M, Ruiz F, Cichewicz RH, McHardy SF, Mooberry SL..  (2017)  Structure-Activity Relationships of New Natural Product-Based Diaryloxazoles with Selective Activity against Androgen Receptor-Positive Breast Cancer Cells.,  60  (22): [PMID:29053266] [10.1021/acs.jmedchem.7b01228]

Source

Source(1):

• Scientific Literature