2-(2-(3'-(2-Aminoethoxy)-4'-chloro-[1,1'-biphenyl]-3-carboxamido)phenyl)acetic acid

ID: ALA4781889

PubChem CID: 162664841

Max Phase: Preclinical

Molecular Formula: C23H21ClN2O4

Molecular Weight: 424.88

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NCCOc1cc(-c2cccc(C(=O)Nc3ccccc3CC(=O)O)c2)ccc1Cl

Standard InChI:  InChI=1S/C23H21ClN2O4/c24-19-9-8-16(13-21(19)30-11-10-25)15-5-3-6-18(12-15)23(29)26-20-7-2-1-4-17(20)14-22(27)28/h1-9,12-13H,10-11,14,25H2,(H,26,29)(H,27,28)

Standard InChI Key:  CHNOCYSXOAXIMZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   32.9348  -10.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9320   -9.4560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2233   -9.0507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2268  -11.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5174  -11.9109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5168  -12.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2250  -13.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   34.3474   -9.4506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6350   -8.2275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.2259  -13.9541    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   35.0535   -9.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   36.4642   -8.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7500   -7.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0473   -8.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7622  -10.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4705  -10.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4715  -11.4908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.1777  -10.2641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6442  -13.1304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3505  -12.7195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0596  -13.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7659  -12.7148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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  3  7  1  0
  5 13  1  0
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 10 16  1  0
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 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
 27 28  1  0
 28 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4781889

   ---

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: 424.88

Molecular Weight (Monoisotopic): 424.1190

AlogP: 4.22

#Rotatable Bonds: 8

Polar Surface Area: 101.65

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.77

CX Basic pKa: 9.28

CX LogP: 1.73

CX LogD: 1.73

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.50

Np Likeness Score: -1.00

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