1-(2-phenyl-1H-indol-5-yl)-3-(pyridin-4-ylmethyl)urea

ID: ALA4872111

PubChem CID: 152251005

Max Phase: Preclinical

Molecular Formula: C21H18N4O

Molecular Weight: 342.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccncc1)Nc1ccc2[nH]c(-c3ccccc3)cc2c1

Standard InChI:  InChI=1S/C21H18N4O/c26-21(23-14-15-8-10-22-11-9-15)24-18-6-7-19-17(12-18)13-20(25-19)16-4-2-1-3-5-16/h1-13,25H,14H2,(H2,23,24,26)

Standard InChI Key:  WFIKAUZHKZNKKY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    2.4433  -16.0838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1510  -15.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8587  -16.0838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5664  -15.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7356  -15.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1510  -14.8580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0279  -16.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3208  -15.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3895  -16.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3890  -16.8981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3258  -17.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0301  -16.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2728  -16.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2678  -14.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5635  -14.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9805  -14.8622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9811  -15.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7553  -15.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2332  -15.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7543  -14.6103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0504  -15.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4552  -15.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2716  -15.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6805  -15.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2670  -14.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4519  -14.5628    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
  1  5  1  0
  2  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  4 13  2  0
 13 17  1  0
 16 14  1  0
 14 15  2  0
 15  4  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 16  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4872111

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 342.40

Molecular Weight (Monoisotopic): 342.1481

AlogP: 4.55

#Rotatable Bonds: 4

Polar Surface Area: 69.81

Molecular Species: NEUTRAL

HBA: 2

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.31

CX Basic pKa: 5.02

CX LogP: 3.27

CX LogD: 3.27

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.51

Np Likeness Score: -1.60

References

1. Akiu M, Tsuji T, Sogawa Y, Terayama K, Yokoyama M, Tanaka J, Asano D, Sakurai K, Sergienko E, Sessions EH, Gardell SJ, Pinkerton AB, Nakamura T..  (2021)  Discovery of 1-[2-(1-methyl-1H-pyrazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-3-(pyridin-4-ylmethyl)urea as a potent NAMPT (nicotinamide phosphoribosyltransferase) activator with attenuated CYP inhibition.,  43  [PMID:33887438] [10.1016/j.bmcl.2021.128048]

Source

Source(1):

• Scientific Literature