Diethyl 3-(4-(2,4-dichlorobenzamido)piperidin-1-yl)propylphosphonate

ID: ALA4072002

PubChem CID: 137639281

Max Phase: Preclinical

Molecular Formula: C19H29Cl2N2O4P

Molecular Weight: 451.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOP(=O)(CCCN1CCC(NC(=O)c2ccc(Cl)cc2Cl)CC1)OCC

Standard InChI:  InChI=1S/C19H29Cl2N2O4P/c1-3-26-28(25,27-4-2)13-5-10-23-11-8-16(9-12-23)22-19(24)17-7-6-15(20)14-18(17)21/h6-7,14,16H,3-5,8-13H2,1-2H3,(H,22,24)

Standard InChI Key:  ZWVREVXTSMJCAO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   37.1973  -11.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1961  -12.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9042  -12.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6139  -12.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6110  -11.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9024  -11.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9000  -10.2559    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   36.4881  -12.7095    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   39.3172  -11.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0264  -11.4730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.3141  -10.2499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.7326  -11.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4404  -11.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1445  -11.0626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1456  -10.2450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.4366   -9.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7263  -10.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8534   -9.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5611  -10.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2688   -9.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9765  -10.2451    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   45.6842   -9.8365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.9765  -11.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.6802  -10.6524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.6793  -11.4696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.6842   -9.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.3919   -8.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.3865  -11.8789    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  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 21 24  1  0
 24 25  1  0
 22 26  1  0
 26 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4072002

   ---

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: 451.33

Molecular Weight (Monoisotopic): 450.1242

AlogP: 4.84

#Rotatable Bonds: 10

Polar Surface Area: 67.87

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.53

CX Basic pKa: 8.88

CX LogP: 2.66

CX LogD: 1.17

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.52

Np Likeness Score: -1.38

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