4-Amino-N-(3-(6-(3-pyrrolidin-1-yl)propoxy)benzo[d]oxazol-2-yl)phenylbenzamide

ID: ALA4062511

PubChem CID: 137635490

Max Phase: Preclinical

Molecular Formula: C27H28N4O3

Molecular Weight: 456.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(C(=O)Nc2cccc(-c3nc4ccc(OCCCN5CCCC5)cc4o3)c2)cc1

Standard InChI:  InChI=1S/C27H28N4O3/c28-21-9-7-19(8-10-21)26(32)29-22-6-3-5-20(17-22)27-30-24-12-11-23(18-25(24)34-27)33-16-4-15-31-13-1-2-14-31/h3,5-12,17-18H,1-2,4,13-16,28H2,(H,29,32)

Standard InChI Key:  JBZIUIXKIUHCQZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   13.9207  -11.1325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3293  -10.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9207   -9.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3293   -9.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1506   -9.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5592   -9.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1506  -10.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3293  -11.8432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0994  -11.1325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6908  -10.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8695  -10.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4609   -9.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8695   -9.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6908   -9.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0994   -9.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1594  -10.3768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6396   -9.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1594   -9.0496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3781   -9.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3781  -10.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6690  -10.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9599  -10.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9599   -9.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6690   -8.8981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2508  -10.5366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5376  -10.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8285  -10.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1194  -10.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4103  -10.5366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3222  -11.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5196  -11.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1110  -10.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6589  -10.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5592   -8.2939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  2  7  2  0
  1  8  2  0
  1  9  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 16 20  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
 20 21  2  0
 26 27  1  0
 27 28  1  0
 25 26  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 29 33  1  0
 28 29  1  0
 22 25  1  0
 12 17  1  0
  9 10  1  0
  5 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4062511

   ---

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: 456.55

Molecular Weight (Monoisotopic): 456.2161

AlogP: 5.19

#Rotatable Bonds: 8

Polar Surface Area: 93.62

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.27

CX LogP: 3.93

CX LogD: 2.07

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.28

Np Likeness Score: -1.66

References

1. Roy S, Mukherjee A, Paul B, Rahaman O, Roy S, Maithri G, Ramya B, Pal S, Ganguly D, Talukdar A..  (2017)  Design and development of benzoxazole derivatives with toll-like receptor 9 antagonism.,  134  [PMID:28437629] [10.1016/j.ejmech.2017.03.086]

Source

Source(1):

• Scientific Literature