2-Methyl-N-[(6-(5-(4-[(3-methylbut-2-en-1-yl)oxy]phenyl)oxazol-2-yl)pyridin-3-yl)methyl]propan-1-amine

ID: ALA4063779

PubChem CID: 137634648

Max Phase: Preclinical

Molecular Formula: C24H29N3O2

Molecular Weight: 391.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=CCOc1ccc(-c2cnc(-c3ccc(CNCC(C)C)cn3)o2)cc1

Standard InChI:  InChI=1S/C24H29N3O2/c1-17(2)11-12-28-21-8-6-20(7-9-21)23-16-27-24(29-23)22-10-5-19(15-26-22)14-25-13-18(3)4/h5-11,15-16,18,25H,12-14H2,1-4H3

Standard InChI Key:  RQPWLALVJUDTKJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    2.7057   -7.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4215   -8.3513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1331   -7.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8490   -8.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5648   -7.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5648   -7.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8490   -6.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1331   -7.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0308   -7.0390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5840   -6.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1715   -5.7109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3655   -5.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2807   -6.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4043   -6.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7356   -7.2687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5551   -7.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0418   -6.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7030   -5.9321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8844   -5.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8622   -6.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1978   -7.5287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7086   -8.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0409   -8.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8613   -9.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9916   -8.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2767   -7.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5706   -8.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2761   -7.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5535   -9.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  3  8  2  0
  2  3  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  9 13  1  0
  6 13  1  0
  1  2  1  0
 10 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 14  2  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
  1 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 23 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4063779

   ---

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: 391.52

Molecular Weight (Monoisotopic): 391.2260

AlogP: 5.49

#Rotatable Bonds: 9

Polar Surface Area: 60.18

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.20

CX LogP: 4.68

CX LogD: 2.89

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: -0.48

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]

Source

Source(1):

• Scientific Literature