US9340517, 364

ID: ALA3986770

PubChem CID: 46897054

Max Phase: Preclinical

Molecular Formula: C21H22Cl4N4O2

Molecular Weight: 504.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC[C@@H]1N[C@H](CNC(=O)c2ccc(Cl)c(Cl)c2)CCN(Cc2cc(Cl)cc(Cl)c2)C1=O

Standard InChI:  InChI=1S/C21H22Cl4N4O2/c22-14-5-12(6-15(23)8-14)11-29-4-3-16(28-19(9-26)21(29)31)10-27-20(30)13-1-2-17(24)18(25)7-13/h1-2,5-8,16,19,28H,3-4,9-11,26H2,(H,27,30)/t16-,19-/m0/s1

Standard InChI Key:  PCFLAUAVIGOSHR-LPHOPBHVSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  1  0  0  0  0  0999 V2000
    3.9660    0.1648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1510   -0.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6852   -0.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3514    1.0778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0030    3.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039    3.9799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3069    5.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2687    6.0825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6077    6.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6130    7.7294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9146    8.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2110    7.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2523    8.3168    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2059    6.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2430    5.6169    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9043    5.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3515    1.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6852   -0.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.5574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4048   -2.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9016   -3.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5571   -4.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0533   -4.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5777   -5.5556    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.8940   -3.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2386   -1.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9111   -0.8909    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7424   -1.7778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2707   -2.6386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  5  6  1  1
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 10  1  0
  5 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 29 22  1  0
 20 30  1  0
 30  3  1  0
 30 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3986770

   N-[[(3S,5S)-3-(aminomethyl)-1-[(3,5-dichlorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]-3,4-dichlorobenzamide

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: 504.25

Molecular Weight (Monoisotopic): 502.0497

AlogP: 3.75

#Rotatable Bonds: 6

Polar Surface Area: 87.46

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.32

CX LogP: 3.31

CX LogD: 2.34

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.56

Np Likeness Score: -0.94

References

1.  (2016)  Methods of modulating the activity of the MC5 receptor and treatment of conditions related to this receptor, 

Source

Source(1):

• BindingDB Database