2-{[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl](methyl)amino}-N-[(2-chlorophenyl)methyl]-4-hydroxybutanamide

ID: ALA4794776

PubChem CID: 162674179

Max Phase: Preclinical

Molecular Formula: C26H31ClN2O2S2

Molecular Weight: 503.13

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccsc1C(=CCCN(C)C(CCO)C(=O)NCc1ccccc1Cl)c1sccc1C

Standard InChI:  InChI=1S/C26H31ClN2O2S2/c1-18-11-15-32-24(18)21(25-19(2)12-16-33-25)8-6-13-29(3)23(10-14-30)26(31)28-17-20-7-4-5-9-22(20)27/h4-5,7-9,11-12,15-16,23,30H,6,10,13-14,17H2,1-3H3,(H,28,31)

Standard InChI Key:  IJIMBHRRVMFBCK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    4.3167   -3.1834    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1417   -3.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3984   -2.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7292   -1.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0641   -2.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6258   -3.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4464   -3.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2894   -4.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4834   -4.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3963   -5.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1496   -5.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7022   -5.3153    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.1835   -2.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8723   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9306   -4.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7511   -4.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2353   -5.0168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0559   -4.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8988   -5.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5401   -5.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3923   -4.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2130   -4.0930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9082   -3.5103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2036   -6.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6878   -7.0209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5493   -3.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3699   -3.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8531   -3.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6730   -3.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0102   -3.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5214   -2.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7033   -2.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2171   -1.8372    0.0000 Cl  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 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4794776

   ---

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: 503.13

Molecular Weight (Monoisotopic): 502.1515

AlogP: 5.90

#Rotatable Bonds: 11

Polar Surface Area: 52.57

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.91

CX Basic pKa: 8.03

CX LogP: 5.90

CX LogD: 5.18

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.34

Np Likeness Score: -0.78

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]

Source

Source(1):

• Scientific Literature