((S)-1-Benzyl-pyrrolidin-3-ylmethyl)-[2-(5-bromo-2-methoxy-phenyl)-thiazol-4-ylmethyl]-amine

ID: ALA2111528

PubChem CID: 71454405

Max Phase: Preclinical

Molecular Formula: C23H26BrN3OS

Molecular Weight: 472.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Br)cc1-c1nc(CNCC2CCN(Cc3ccccc3)C2)cs1

Standard InChI:  InChI=1S/C23H26BrN3OS/c1-28-22-8-7-19(24)11-21(22)23-26-20(16-29-23)13-25-12-18-9-10-27(15-18)14-17-5-3-2-4-6-17/h2-8,11,16,18,25H,9-10,12-15H2,1H3

Standard InChI Key:  FYSSSSIVDTYBFD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    6.0729   -0.3039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5870   -0.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3487    0.8200    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.5974    0.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3446   -2.5016    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1479    1.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5870   -1.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8752    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7077   -1.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3196   -3.3258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8752   -1.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7962   -0.4412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9949   -1.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0438   -2.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1634   -0.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4215    0.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1634   -1.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8191   -1.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4392    0.0083    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.2987   -1.6525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5828   -3.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6203   -0.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5579   -4.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8960   -3.2758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2987   -2.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1593   -3.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8211   -4.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1218   -4.4871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  1  1  0
  5  2  1  0
  6 10  1  0
  7  4  1  0
  8  3  1  0
  9  3  2  0
 10 14  1  0
 11  6  1  0
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 13 17  1  0
 14 23  1  0
 15 19  1  0
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 18 16  2  0
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 20 16  1  0
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 22 11  1  0
 23 13  1  0
 24 22  1  0
 25 22  2  0
 26 21  1  0
 27 25  1  0
 28 24  2  0
 29 27  2  0
  5  7  2  0
 18 12  1  0
 15  6  1  0
 29 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2111528

   1-(1-benzylpyrrolidin-3-yl)-N-[[2-(5-bromo-2-methoxyphenyl)-1,3-thiazol-4-yl]methyl]methanamine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 472.45

Molecular Weight (Monoisotopic): 471.0980

AlogP: 5.19

#Rotatable Bonds: 8

Polar Surface Area: 37.39

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.30

CX LogP: 4.72

CX LogD: 2.78

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: -1.70

References

1. Einsiedel J, Thomas C, Hübner H, Gmeiner P..  (2000)  Phenyloxazoles and phenylthiazoles as benzamide bioisosteres: synthesis and dopamine receptor binding profiles.,  10  (17): [PMID:10987445] [10.1016/s0960-894x(00)00405-4]

Source

Source(1):

• Scientific Literature