1-Methyl-N-(3-(6-(3-(pyrrolidin-1-yl)propoxy)benzo[d]oxazol-2-yl)phenyl)piperidine-4-amine

ID: ALA4082132

PubChem CID: 137647183

Max Phase: Preclinical

Molecular Formula: C26H34N4O2

Molecular Weight: 434.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCC(Nc2cccc(-c3nc4ccc(OCCCN5CCCC5)cc4o3)c2)CC1

Standard InChI:  InChI=1S/C26H34N4O2/c1-29-15-10-21(11-16-29)27-22-7-4-6-20(18-22)26-28-24-9-8-23(19-25(24)32-26)31-17-5-14-30-12-2-3-13-30/h4,6-9,18-19,21,27H,2-3,5,10-17H2,1H3

Standard InChI Key:  LKJHXIBCNZAWKC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   18.6246  -11.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2160  -12.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3989  -12.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9903  -11.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3989  -10.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2160  -10.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1731  -11.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7645  -10.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9473  -10.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5387  -10.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9473   -9.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7645   -9.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1731  -10.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2414  -10.7416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7215  -10.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2414   -9.4143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4641   -9.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4641  -10.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7550  -10.8972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0459  -10.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0459   -9.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7550   -9.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3410  -10.8972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6319  -10.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9269  -10.8972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2178  -10.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5088  -10.8972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4247  -11.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6263  -11.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2177  -11.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7615  -10.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4418  -11.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  4  7  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 13  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 14 18  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 18 19  2  0
 24 25  1  0
 25 26  1  0
 23 24  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 27 31  1  0
 26 27  1  0
 20 23  1  0
 10 15  1  0
  7  8  1  0
  1 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4082132

   ---

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: 434.58

Molecular Weight (Monoisotopic): 434.2682

AlogP: 4.87

#Rotatable Bonds: 8

Polar Surface Area: 53.77

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.40

CX LogP: 3.17

CX LogD: -0.11

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.51

Np Likeness Score: -1.60

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]

2. Pal S, Paul B, Bandopadhyay P, Preethy N, Sarkar D, Rahaman O, Goon S, Roy S, Ganguly D, Talukdar A..  (2021)  Synthesis and characterization of new potent TLR7 antagonists based on analysis of the binding mode using biomolecular simulations.,  210  [PMID:33189437] [10.1016/j.ejmech.2020.112978]

Source

Source(1):

• Scientific Literature