N-benzyl-2-((4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl)(methyl)amino)-4-hydroxypentanamide

ID: ALA4793917

PubChem CID: 162673648

Max Phase: Preclinical

Molecular Formula: C27H34N2O2S2

Molecular Weight: 482.72

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccsc1C(=CCCN(C)C(CC(C)O)C(=O)NCc1ccccc1)c1sccc1C

Standard InChI:  InChI=1S/C27H34N2O2S2/c1-19-12-15-32-25(19)23(26-20(2)13-16-33-26)11-8-14-29(4)24(17-21(3)30)27(31)28-18-22-9-6-5-7-10-22/h5-7,9-13,15-16,21,24,30H,8,14,17-18H2,1-4H3,(H,28,31)

Standard InChI Key:  MEUUMBPFQFBEEL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    3.8790   -3.3166    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7039   -3.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608   -2.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2915   -2.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6265   -2.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1881   -3.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0086   -3.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8516   -4.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0457   -4.9040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9585   -5.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7118   -6.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2644   -5.4483    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7457   -2.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4347   -4.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4927   -4.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3133   -4.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7974   -5.1499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6179   -5.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4610   -5.9032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1021   -5.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9544   -4.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7749   -4.2261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4702   -3.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7657   -6.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2498   -7.1538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9341   -3.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1106   -3.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4127   -4.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2355   -3.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5771   -3.2312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0898   -2.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2686   -2.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9451   -6.5711    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
 24 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4793917

   ---

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: 482.72

Molecular Weight (Monoisotopic): 482.2062

AlogP: 5.64

#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: 8.07

CX LogP: 5.72

CX LogD: 4.96

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.37

Np Likeness Score: -0.42

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,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