1-benzyl-3-(4-bromo-2-methylphenyl)-1-(1-(pentan-2-yl)piperidin-4-yl)urea

ID: ALA4104429

PubChem CID: 126711384

Max Phase: Preclinical

Molecular Formula: C25H34BrN3O

Molecular Weight: 472.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC(C)N1CCC(N(Cc2ccccc2)C(=O)Nc2ccc(Br)cc2C)CC1

Standard InChI:  InChI=1S/C25H34BrN3O/c1-4-8-20(3)28-15-13-23(14-16-28)29(18-21-9-6-5-7-10-21)25(30)27-24-12-11-22(26)17-19(24)2/h5-7,9-12,17,20,23H,4,8,13-16,18H2,1-3H3,(H,27,30)

Standard InChI Key:  MYUASMLCKODDJG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   29.0378   -8.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0366   -9.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7447  -10.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4543   -9.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4515   -8.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7429   -8.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3286  -10.1093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6212   -9.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9132  -10.1082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6218   -8.8830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2058   -9.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2106   -8.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5073   -8.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7968   -8.8765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7942   -9.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5021  -10.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9125  -10.9254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2045  -11.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4980  -10.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7904  -11.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7893  -12.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5017  -12.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2063  -12.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0910   -8.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0948   -7.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3814   -8.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6756   -8.4582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9660   -8.8635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7445  -10.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1577   -8.4669    0.0000 Br  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
  2  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
 11 12  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  9 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 14 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
  3 29  1  0
  5 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4104429

   ---

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: 472.47

Molecular Weight (Monoisotopic): 471.1885

AlogP: 6.44

#Rotatable Bonds: 7

Polar Surface Area: 35.58

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.49

CX Basic pKa: 9.45

CX LogP: 6.10

CX LogD: 4.06

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.50

Np Likeness Score: -1.91

References

1. Hammill JT, Bhasin D, Scott DC, Min J, Chen Y, Lu Y, Yang L, Kim HS, Connelly MC, Hammill C, Holbrook G, Jeffries C, Singh B, Schulman BA, Guy RK..  (2018)  Discovery of an Orally Bioavailable Inhibitor of Defective in Cullin Neddylation 1 (DCN1)-Mediated Cullin Neddylation.,  61  (7): [PMID:29547693] [10.1021/acs.jmedchem.7b01282]

Source

Source(1):

• Scientific Literature