rel-cis-((4,4-bis(3-methylthiophen-2-yl)but-3-enyl)(methyl)amino)cyclohexanecarboxylic acid

ID: ALA2326022

PubChem CID: 71584061

Max Phase: Preclinical

Molecular Formula: C22H29NO2S2

Molecular Weight: 403.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccsc1C(=CCCN(C)[C@@H]1CCCC[C@@H]1C(=O)O)c1sccc1C

Standard InChI:  InChI=1S/C22H29NO2S2/c1-15-10-13-26-20(15)18(21-16(2)11-14-27-21)8-6-12-23(3)19-9-5-4-7-17(19)22(24)25/h8,10-11,13-14,17,19H,4-7,9,12H2,1-3H3,(H,24,25)/t17-,19+/m0/s1

Standard InChI Key:  WVEAQTILSGURKS-PKOBYXMFSA-N

Molfile:  

     RDKit          2D

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    1.3474  -13.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0551  -13.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7628  -13.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4706  -13.6611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1783  -13.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0723  -13.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6397  -14.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643  -12.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9580  -12.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3666  -12.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8239  -13.5878    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0226  -14.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2338  -15.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0511  -15.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3035  -14.9623    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.4481  -11.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8048  -14.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4725  -14.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7630  -14.8799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7610  -15.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4669  -16.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1764  -15.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1800  -14.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8881  -14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5961  -14.8798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8897  -13.6533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  1  0
  1  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  7  1  0
  8 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16  8  1  0
  9 17  1  0
 13 18  1  0
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 19  5  1  1
 24 25  1  1
 25 26  1  0
 25 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2326022

   (1S,2R)-2-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl-methylamino]cyclohexane-1-carboxylic acid

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: 403.61

Molecular Weight (Monoisotopic): 403.1640

AlogP: 5.82

#Rotatable Bonds: 7

Polar Surface Area: 40.54

Molecular Species: ZWITTERION

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.15

CX Basic pKa: 10.73

CX LogP: 3.55

CX LogD: 3.55

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.63

Np Likeness Score: -0.32

References

1. Vogensen SB, Jørgensen L, Madsen KK, Borkar N, Wellendorph P, Skovgaard-Petersen J, Schousboe A, White HS, Krogsgaard-Larsen P, Clausen RP..  (2013)  Selective mGAT2 (BGT-1) GABA uptake inhibitors: design, synthesis, and pharmacological characterization.,  56  (5): [PMID:23398473] [10.1021/jm301872x]

2. 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