(trans)-(S)-4-(4-fluorophenoxy)-N-methyl-N-(4-((3-methylpiperazin-1-yl)methyl)phenyl)cyclohexanecarboxamide

ID: ALA5197045

PubChem CID: 56960873

Max Phase: Preclinical

Molecular Formula: C26H34FN3O2

Molecular Weight: 439.58

Names and Identifiers

Canonical SMILES:  C[C@H]1CN(Cc2ccc(N(C)C(=O)[C@H]3CC[C@H](Oc4ccc(F)cc4)CC3)cc2)CCN1

Standard InChI:  InChI=1S/C26H34FN3O2/c1-19-17-30(16-15-28-19)18-20-3-9-23(10-4-20)29(2)26(31)21-5-11-24(12-6-21)32-25-13-7-22(27)8-14-25/h3-4,7-10,13-14,19,21,24,28H,5-6,11-12,15-18H2,1-2H3/t19-,21-,24-/m0/s1

Standard InChI Key:  XSRJNPUCQNDPRR-PTLVVNQVSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   -3.5696    1.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8552    1.8571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1407    1.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1407    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8552    0.2070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5696    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8552   -0.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1408   -1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4263   -0.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147   -1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147   -1.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246   -2.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1408   -1.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4263    1.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004   -2.2671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -1.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004   -3.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -1.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4281   -2.2671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0002   -0.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0002    0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4281    0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4281   -0.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138    1.4442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4281    1.8567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4283    2.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1408    3.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8554    2.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8570    1.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455    1.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5696    3.0919    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  1  6  1  0
  6  5  1  0
  5  7  1  0
  7  8  1  0
  9  8  2  0
 10  9  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
  8 13  1  0
  3 14  1  1
 11 15  1  0
 15 16  1  0
 15 17  1  0
 18 16  1  1
 16 19  2  0
 20 18  1  0
 21 20  1  0
 22 21  1  0
 23 22  1  0
 24 23  1  0
 18 24  1  0
 22 25  1  6
 25 26  1  0
 27 26  2  0
 28 27  1  0
 29 28  2  0
 30 29  1  0
 31 30  2  0
 26 31  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5197045

   4-(4-fluorophenoxy)-N-methyl-N-[4-[[(3S)-3-methylpiperazin-1-yl]methyl]phenyl]cyclohexane-1-carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 439.58

Molecular Weight (Monoisotopic): 439.2635

AlogP: 4.22

#Rotatable Bonds: 6

Polar Surface Area: 44.81

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.33

CX LogP: 4.10

CX LogD: 2.18

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.73

Np Likeness Score: -1.12

References

1. Toda N, Shida T, Takano R, Katagiri T, Hirouchi M, Abe M, Soma K, Nakagami Y, Yamazaki M..  (2022)  Discovery of DS-3801b, a non-macrolide GPR38 agonist with N-methylanilide structure.,  59  [PMID:35051575] [10.1016/j.bmcl.2022.128554]

Source

Source(1):

• Scientific Literature