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

ID: ALA4762252

PubChem CID: 162659558

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-/m1/s1

Standard InChI Key:  ZOPOXKJETIWBQP-LJQANCHMSA-N

Molfile:  

 
     RDKit          2D

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    8.3027   -3.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3016   -3.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0163   -4.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7328   -3.9727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7300   -3.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0146   -2.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0181   -5.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3019   -5.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -6.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0162   -6.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7331   -6.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7302   -5.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4429   -2.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1589   -3.1368    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4398   -1.9020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0172   -7.6833    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.8719   -2.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5879   -3.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8687   -1.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5816   -1.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5786   -0.6564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2977   -1.8912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5879   -3.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3030   -4.3650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0169   -3.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0111   -3.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2954   -2.7145    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
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  3  7  1  0
  5 13  1  0
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 10 16  1  0
 17 14  1  6
 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:

   

   ALA4762252

   ---

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