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

ID: ALA4793036

PubChem CID: 162670620

Max Phase: Preclinical

Molecular Formula: C21H17ClN2O3

Molecular Weight: 380.83

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)C[C@H](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)/t19-/m0/s1

Standard InChI Key:  ZOPOXKJETIWBQP-IBGZPJMESA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    8.2241   -3.1160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2230   -3.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9310   -4.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6407   -3.9351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6379   -3.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9293   -2.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9327   -5.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2233   -5.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2227   -6.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9309   -6.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6410   -6.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6381   -5.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3440   -2.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0533   -3.1071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3410   -1.8840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9318   -7.6106    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.7595   -2.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4687   -3.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7564   -1.8786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4625   -1.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4595   -0.6502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1718   -1.8733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4687   -3.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1771   -4.3237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8842   -3.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8785   -3.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1695   -2.6888    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  1
 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:

   

   ALA4793036

   ---

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