2-[2-[[3-[4-chloro-2-fluoro-3-[[(3R)-3-piperidyl]oxy]phenyl]benzoyl]amino]phenyl]acetic acid

ID: ALA4763307

PubChem CID: 162659507

Max Phase: Preclinical

Molecular Formula: C26H24ClFN2O4

Molecular Weight: 482.94

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)Cc1ccccc1NC(=O)c1cccc(-c2ccc(Cl)c(O[C@@H]3CCCNC3)c2F)c1

Standard InChI:  InChI=1S/C26H24ClFN2O4/c27-21-11-10-20(24(28)25(21)34-19-8-4-12-29-15-19)16-6-3-7-18(13-16)26(33)30-22-9-2-1-5-17(22)14-23(31)32/h1-3,5-7,9-11,13,19,29H,4,8,12,14-15H2,(H,30,33)(H,31,32)/t19-/m1/s1

Standard InChI Key:  GFZGZLKOWGFBSB-LJQANCHMSA-N

Molfile:  

 
     RDKit          2D

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    1.8307  -26.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456  -27.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2619  -26.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8305  -29.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5454  -29.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2623  -29.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2593  -28.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9721  -25.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6880  -26.0282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9689  -24.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5463  -30.5746    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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    6.8277  -25.6117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8251  -24.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1041  -24.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3946  -24.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1164  -26.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8314  -27.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8324  -28.0877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5453  -26.8493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9781  -29.7430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6912  -29.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4015  -29.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1125  -29.3309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1140  -28.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3983  -28.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6812  -28.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9728  -28.0957    0.0000 F   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
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  3  7  1  0
  5 13  1  0
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 10 16  1  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 18 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 11 27  1  0
 28 27  1  6
 28 29  1  0
 28 33  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 12 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4763307

   ---

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: 482.94

Molecular Weight (Monoisotopic): 482.1409

AlogP: 5.16

#Rotatable Bonds: 7

Polar Surface Area: 87.66

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.74

CX Basic pKa: 9.36

CX LogP: 2.57

CX LogD: 2.56

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.43

Np Likeness Score: -0.89

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