3-[[3-(4-chlorophenyl)benzoyl]amino]-3-(3-pyridyl)propanoic acid

ID: ALA4782840

PubChem CID: 162665135

Max Phase: Preclinical

Molecular Formula: C21H17ClN2O3

Molecular Weight: 380.83

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)CC(NC(=O)c1cccc(-c2ccc(Cl)cc2)c1)c1cccnc1

Standard InChI:  InChI=1S/C21H17ClN2O3/c22-18-8-6-14(7-9-18)15-3-1-4-16(11-15)21(27)24-19(12-20(25)26)17-5-2-10-23-13-17/h1-11,13,19H,12H2,(H,24,27)(H,25,26)

Standard InChI Key:  ZOPOXKJETIWBQP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    1.2698   -3.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2686   -4.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9767   -4.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6863   -4.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6835   -3.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9749   -2.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9783   -5.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2689   -5.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2684   -6.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9765   -6.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6867   -6.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6837   -5.7264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -2.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0989   -3.2680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3866   -2.0449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9774   -7.7715    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.8051   -2.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5143   -3.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8020   -2.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5082   -1.6283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5051   -0.8112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2174   -2.0343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5143   -4.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2227   -4.4846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9299   -4.0733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9241   -3.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2152   -2.8498    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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  3  7  1  0
  5 13  1  0
 13 14  1  0
 13 15  2  0
 10 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 18 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4782840

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 380.83

Molecular Weight (Monoisotopic): 380.0928

AlogP: 4.35

#Rotatable Bonds: 6

Polar Surface Area: 79.29

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.88

CX Basic pKa: 4.85

CX LogP: 2.71

CX LogD: 0.48

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.67

Np Likeness Score: -1.07

References

1. Velcicky J,Wilcken R,Cotesta S,Janser P,Schlapbach A,Wagner T,Piechon P,Villard F,Bouhelal R,Piller F,Harlfinger S,Stringer R,Fehlmann D,Kaupmann K,Littlewood-Evans A,Haffke M,Gommermann N.  (2020)  Discovery and Optimization of Novel SUCNR1 Inhibitors: Design of Zwitterionic Derivatives with a Salt Bridge for the Improvement of Oral Exposure.,  63  (17): [PMID:32856916] [10.1021/acs.jmedchem.0c01020]

Source

Source(1):

• Scientific Literature