(1R,2S)-2-((2-(bis(4-(Trifluoromethyl)phenyl)methoxy)ethyl)(methyl)amino)cyclohexanecarboxylic acid

ID: ALA3403564

PubChem CID: 118729872

Max Phase: Preclinical

Molecular Formula: C25H27F6NO3

Molecular Weight: 503.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(CCOC(c1ccc(C(F)(F)F)cc1)c1ccc(C(F)(F)F)cc1)[C@H]1CCCC[C@H]1C(=O)O

Standard InChI:  InChI=1S/C25H27F6NO3/c1-32(21-5-3-2-4-20(21)23(33)34)14-15-35-22(16-6-10-18(11-7-16)24(26,27)28)17-8-12-19(13-9-17)25(29,30)31/h6-13,20-22H,2-5,14-15H2,1H3,(H,33,34)/t20-,21+/m1/s1

Standard InChI Key:  HTIZULDALLMMIY-RTWAWAEBSA-N

Molfile:  

     RDKit          2D

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    6.4990   -0.7409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2003   -1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0031   -3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0432   -3.5993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1023   -3.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1028   -5.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8041   -5.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5047   -5.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5042   -3.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8046   -7.4904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7654   -8.0904    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.8045   -8.6904    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.9891    1.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0307    0.9318    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.9845    2.7275    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.0259    2.1316    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  1  0
  4  5  1  0
  6  5  1  6
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  1 16  1  0
  1 17  1  0
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 20 21  1  0
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 22 16  1  0
 17 23  2  0
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 27 17  1  0
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 28 29  1  0
 28 30  1  0
 28 31  1  0
 20 32  1  0
 32 33  1  0
 32 34  1  0
 32 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3403564

   ---

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: 503.48

Molecular Weight (Monoisotopic): 503.1895

AlogP: 6.41

#Rotatable Bonds: 8

Polar Surface Area: 49.77

Molecular Species: ZWITTERION

HBA: 3

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.29

CX Basic pKa: 9.94

CX LogP: 3.85

CX LogD: 3.85

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.42

Np Likeness Score: -0.44

References

1. Vogensen SB, Jørgensen L, Madsen KK, Jurik A, Borkar N, Rosatelli E, Nielsen B, Ecker GF, Schousboe A, Clausen RP..  (2015)  Structure activity relationship of selective GABA uptake inhibitors.,  23  (10): [PMID:25882526] [10.1016/j.bmc.2015.03.060]

Source

Source(1):

• Scientific Literature