N-Benzyl-3-(((5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl)methyl)-amino)benzamide

ID: ALA4096791

PubChem CID: 137653406

Max Phase: Preclinical

Molecular Formula: C22H19N5O2

Molecular Weight: 385.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccccc1)c1cccc(NCc2nnc(-c3ccncc3)o2)c1

Standard InChI:  InChI=1S/C22H19N5O2/c28-21(25-14-16-5-2-1-3-6-16)18-7-4-8-19(13-18)24-15-20-26-27-22(29-20)17-9-11-23-12-10-17/h1-13,24H,14-15H2,(H,25,28)

Standard InChI Key:  SVKLMBZNMVZHTI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   12.9277  -11.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2857  -11.7766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4020  -12.5903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1636  -12.8904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8137  -12.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6900  -11.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5706  -12.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8123  -13.4742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6304  -13.4921    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9016  -12.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2477  -12.2159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6983  -12.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2867  -13.0606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6486  -13.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4331  -13.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6508  -12.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0697  -11.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2753  -12.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0658  -12.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2789  -11.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0718  -10.8264    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6994  -10.4600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2809  -10.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0738   -9.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6538  -10.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4460  -10.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6558   -9.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0714   -8.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2814   -9.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  7  1  0
 10 12  1  0
 12 13  1  0
 19 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 13 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4096791

   ---

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: 385.43

Molecular Weight (Monoisotopic): 385.1539

AlogP: 3.67

#Rotatable Bonds: 7

Polar Surface Area: 92.94

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.44

CX LogP: 1.83

CX LogD: 1.83

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.50

Np Likeness Score: -1.84

References

1. Okawa T, Aramaki Y, Yamamoto M, Kobayashi T, Fukumoto S, Toyoda Y, Henta T, Hata A, Ikeda S, Kaneko M, Hoffman ID, Sang BC, Zou H, Kawamoto T..  (2017)  Design, Synthesis, and Evaluation of the Highly Selective and Potent G-Protein-Coupled Receptor Kinase 2 (GRK2) Inhibitor for the Potential Treatment of Heart Failure.,  60  (16): [PMID:28699740] [10.1021/acs.jmedchem.7b00443]

Source

Source(1):

• Scientific Literature