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

ID: ALA4791625

PubChem CID: 162672113

Max Phase: Preclinical

Molecular Formula: C26H31FN2O2S2

Molecular Weight: 486.68

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccsc1C(=CCCN(C)C(CCO)C(=O)NCc1ccc(F)cc1)c1sccc1C

Standard InChI:  InChI=1S/C26H31FN2O2S2/c1-18-11-15-32-24(18)22(25-19(2)12-16-33-25)5-4-13-29(3)23(10-14-30)26(31)28-17-20-6-8-21(27)9-7-20/h5-9,11-12,15-16,23,30H,4,10,13-14,17H2,1-3H3,(H,28,31)

Standard InChI Key:  VNUIURWTSORDDN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    3.4750   -3.0668    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3000   -3.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5568   -2.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875   -1.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2224   -2.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7841   -3.7348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6047   -3.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4477   -4.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -4.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5546   -5.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3079   -5.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8606   -5.1986    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3418   -2.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0306   -4.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0889   -4.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9095   -4.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3937   -4.9002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2142   -4.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0572   -5.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6984   -5.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5506   -4.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3713   -3.9764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0665   -3.3937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3619   -6.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8461   -6.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7077   -3.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5282   -3.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0114   -3.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8313   -3.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1685   -2.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6798   -2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8616   -2.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9890   -2.8824    0.0000 F   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
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4791625

   ---

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: 486.68

Molecular Weight (Monoisotopic): 486.1811

AlogP: 5.39

#Rotatable Bonds: 11

Polar Surface Area: 52.57

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.03

CX LogP: 5.44

CX LogD: 4.72

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.38

Np Likeness Score: -0.71

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