Methyl 4-((4-(2,4-dichlorobenzamido)piperidin-1-yl)methyl)benzoate

ID: ALA4090080

PubChem CID: 137642163

Max Phase: Preclinical

Molecular Formula: C21H22Cl2N2O3

Molecular Weight: 421.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(CN2CCC(NC(=O)c3ccc(Cl)cc3Cl)CC2)cc1

Standard InChI:  InChI=1S/C21H22Cl2N2O3/c1-28-21(27)15-4-2-14(3-5-15)13-25-10-8-17(9-11-25)24-20(26)18-7-6-16(22)12-19(18)23/h2-7,12,17H,8-11,13H2,1H3,(H,24,26)

Standard InChI Key:  FUZAVUNXERGYBW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    1.3606  -21.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3594  -22.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0675  -22.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7771  -22.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7743  -21.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657  -21.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0632  -20.3015    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6514  -22.7552    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4805  -21.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1897  -21.5187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4774  -20.2955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8959  -21.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6037  -21.5160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3078  -21.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3089  -20.2907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5998  -19.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8896  -20.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0166  -19.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7243  -20.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7193  -21.1077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4262  -21.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1348  -21.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1322  -20.2862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4248  -19.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8431  -21.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8442  -22.3325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5503  -21.1057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5492  -20.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  2  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  1  0
 12 13  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 22 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4090080

   ---

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: 421.32

Molecular Weight (Monoisotopic): 420.1007

AlogP: 4.17

#Rotatable Bonds: 5

Polar Surface Area: 58.64

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.53

CX Basic pKa: 7.98

CX LogP: 4.01

CX LogD: 3.33

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.74

Np Likeness Score: -1.53

References

1. Jørgensen L, Al-Khawaja A, Kickinger S, Vogensen SB, Skovgaard-Petersen J, Rosenthal E, Borkar N, Löffler R, Madsen KK, Bräuner-Osborne H, Schousboe A, Ecker GF, Wellendorph P, Clausen RP..  (2017)  Structure-Activity Relationship, Pharmacological Characterization, and Molecular Modeling of Noncompetitive Inhibitors of the Betaine/γ-Aminobutyric Acid Transporter 1 (BGT1).,  60  (21): [PMID:28991462] [10.1021/acs.jmedchem.7b00924]

Source

Source(1):

• Scientific Literature