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

ID: ALA4466321

PubChem CID: 49822299

Max Phase: Preclinical

Molecular Formula: C21H20N2O5

Molecular Weight: 380.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1cccc(-c2ccc(C[C@H](CC(=O)O)NC(=O)CCC(=O)O)cc2)c1

Standard InChI:  InChI=1S/C21H20N2O5/c22-13-15-2-1-3-17(10-15)16-6-4-14(5-7-16)11-18(12-21(27)28)23-19(24)8-9-20(25)26/h1-7,10,18H,8-9,11-12H2,(H,23,24)(H,25,26)(H,27,28)/t18-/m1/s1

Standard InChI Key:  DONZXTXFCDZQJM-GOSISDBHSA-N

Molfile:  

 
     RDKit          2D

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   30.6694   -2.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4908   -2.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9016   -3.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7222   -3.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1316   -2.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7186   -2.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8994   -2.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9491   -2.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3622   -3.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1828   -3.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5912   -2.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1773   -2.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3581   -2.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2608   -3.5266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4395   -3.5266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6694   -4.2384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2608   -4.9503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6694   -5.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4395   -4.9503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.2608   -6.3739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6694   -7.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2608   -7.7935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4908   -7.0858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0309   -2.8189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2137   -2.8189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4395   -2.1112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5837   -1.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9897   -0.6874    0.0000 N   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
 27 28  3  0
 12 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4466321

   4-[[(2R)-1-carboxy-3-[4-(3-cyanophenyl)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: 380.40

Molecular Weight (Monoisotopic): 380.1372

AlogP: 2.59

#Rotatable Bonds: 9

Polar Surface Area: 127.49

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.86

CX Basic pKa: ┄

CX LogP: 2.31

CX LogD: -3.72

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.61

Np Likeness Score: -0.61

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