4-Acetamido-2-((4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl)(methyl)amino)-N-(2-chlorobenzyl)-butanamide

ID: ALA4781266

PubChem CID: 162662801

Max Phase: Preclinical

Molecular Formula: C28H34ClN3O2S2

Molecular Weight: 544.19

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)NCCC(C(=O)NCc1ccccc1Cl)N(C)CCC=C(c1sccc1C)c1sccc1C

Standard InChI:  InChI=1S/C28H34ClN3O2S2/c1-19-12-16-35-26(19)23(27-20(2)13-17-36-27)9-7-15-32(4)25(11-14-30-21(3)33)28(34)31-18-22-8-5-6-10-24(22)29/h5-6,8-10,12-13,16-17,25H,7,11,14-15,18H2,1-4H3,(H,30,33)(H,31,34)

Standard InChI Key:  BYIMWNNOGMXRCA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    3.8207   -4.5583    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6457   -4.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9025   -3.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2332   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5682   -3.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1299   -5.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9504   -5.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2062   -6.6901    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6874   -3.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3764   -5.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4346   -5.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2551   -5.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7392   -6.3917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5598   -6.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7168   -5.4678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4121   -4.8851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7075   -7.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1916   -8.3957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8760   -4.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0524   -4.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3545   -5.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1774   -5.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5190   -4.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0316   -3.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2105   -3.8836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0128   -6.0600    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.8552   -9.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3393   -9.8169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0347   -9.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  2  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  8  1  0
  3 13  1  0
  9 14  1  0
  7 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  2  0
 20 24  1  0
 24 25  1  0
 22 27  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 26  1  0
 28 33  1  0
 25 34  1  0
 34 35  2  0
 34 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4781266

   ---

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: 544.19

Molecular Weight (Monoisotopic): 543.1781

AlogP: 6.04

#Rotatable Bonds: 12

Polar Surface Area: 61.44

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.96

CX Basic pKa: 8.12

CX LogP: 5.62

CX LogD: 4.82

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.29

Np Likeness Score: -0.93

References

1. Zaręba P,Gryzło B,Malawska K,Sałat K,Höfner GC,Nowaczyk A,Fijałkowski Ł,Rapacz A,Podkowa A,Furgała A,Żmudzki P,Wanner KT,Malawska B,Kulig K.  (2020)  Novel mouse GABA uptake inhibitors with enhanced inhibitory activity toward mGAT3/4 and their effect on pain threshold in mice.,  188  [PMID:31901745] [10.1016/j.ejmech.2019.111920]

2. Zaręba P, Sałat K, Höfner GC, Łątka K, Bajda M, Latacz G, Kotniewicz K, Rapacz A, Podkowa A, Maj M, Jóźwiak K, Filipek B, Wanner KT, Malawska B, Kulig K..  (2021)  Development of tricyclic N-benzyl-4-hydroxybutanamide derivatives as inhibitors of GABA transporters mGAT1-4 with anticonvulsant, antinociceptive, and antidepressant activity.,  221  [PMID:34015586] [10.1016/j.ejmech.2021.113512]

Source

Source(1):

• Scientific Literature