4-[[(1R)-1-(carboxymethyl)-2-[4-(3-chloro-2-methoxyphenyl)phenyl]ethyl]amino]-4-oxobutanoic acid

ID: ALA4548017

PubChem CID: 59607804

Max Phase: Preclinical

Molecular Formula: C21H22ClNO6

Molecular Weight: 419.86

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1c(Cl)cccc1-c1ccc(C[C@H](CC(=O)O)NC(=O)CCC(=O)O)cc1

Standard InChI:  InChI=1S/C21H22ClNO6/c1-29-21-16(3-2-4-17(21)22)14-7-5-13(6-8-14)11-15(12-20(27)28)23-18(24)9-10-19(25)26/h2-8,15H,9-12H2,1H3,(H,23,24)(H,25,26)(H,27,28)/t15-/m1/s1

Standard InChI Key:  OZIBRUBAVAJUQK-OAHLLOKOSA-N

Molfile:  

 
     RDKit          2D

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   30.3970  -24.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2184  -24.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6292  -24.9616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4498  -24.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8592  -24.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4462  -23.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6270  -23.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6767  -24.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0898  -24.9624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9104  -24.9616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3188  -24.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9049  -23.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0857  -23.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9884  -24.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1671  -24.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3970  -25.6711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9884  -26.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3970  -27.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1671  -26.3830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9884  -27.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3970  -28.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9884  -29.2262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2184  -28.5185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7585  -24.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9413  -24.2516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1671  -23.5439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6749  -22.8329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0813  -22.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3110  -22.8259    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  5  8  1  0
 14  1  1  1
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 15 24  1  0
 24 25  2  0
 24 26  1  0
 13 27  1  0
 27 28  1  0
 12 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4548017

   4-[[(2R)-1-carboxy-3-[4-(3-chloro-2-methoxyphenyl)phenyl]propan-2-yl]amino]-4-oxobutanoic acid

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: 419.86

Molecular Weight (Monoisotopic): 419.1136

AlogP: 3.38

#Rotatable Bonds: 10

Polar Surface Area: 112.93

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.83

CX Basic pKa: ┄

CX LogP: 2.90

CX LogD: -3.19

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.54

Np Likeness Score: -0.27

References

1. Kawanami T, Karki RG, Cody E, Liu Q, Liang G, Ksander GM, Rigel DF, Schiering N, Gong Y, Coppola GM, Iwaki Y, Sun R, Neubert A, Fan L, Ingles S, D'Arcy A, Villard F, Ramage P, Jeng AY, Leung-Chu J, Liu J, Beil M, Fu F, Chen W, Cumin F, Wiesmann C, Mogi M..  (2020)  Structure-Guided Design of Substituted Biphenyl Butanoic Acid Derivatives as Neprilysin Inhibitors.,  11  (2): [PMID:32071687] [10.1021/acsmedchemlett.9b00578]

Source

Source(1):

• Scientific Literature