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

ID: ALA4568947

PubChem CID: 59607681

Max Phase: Preclinical

Molecular Formula: C20H20N2O7

Molecular Weight: 400.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)CCC(=O)N[C@@H](CC(=O)O)Cc1ccc(-c2cccc([N+](=O)[O-])c2)cc1

Standard InChI:  InChI=1S/C20H20N2O7/c23-18(8-9-19(24)25)21-16(12-20(26)27)10-13-4-6-14(7-5-13)15-2-1-3-17(11-15)22(28)29/h1-7,11,16H,8-10,12H2,(H,21,23)(H,24,25)(H,26,27)/t16-/m1/s1

Standard InChI Key:  HXMVBHNALOHNIT-MRXNPFEDSA-N

Molfile:  

 
     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    5.2540  -13.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0753  -13.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4862  -14.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3067  -14.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7161  -13.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3031  -12.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4839  -12.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5337  -13.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9467  -14.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7673  -14.0988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1758  -13.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7618  -12.6722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9426  -12.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8454  -14.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0240  -14.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2540  -14.8083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8454  -15.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2540  -16.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0240  -15.5201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8454  -16.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2540  -17.6556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8454  -18.3633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0753  -17.6556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6155  -13.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983  -13.3887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0240  -12.6810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1687  -11.9594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7576  -11.2531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9859  -11.9564    0.0000 O   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  2  0
 27 29  1  0
 12 27  1  0
M  CHG  2  27   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4568947

   4-[[(2R)-1-carboxy-3-[4-(3-nitrophenyl)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: 400.39

Molecular Weight (Monoisotopic): 400.1271

AlogP: 2.63

#Rotatable Bonds: 10

Polar Surface Area: 146.84

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.82

CX Basic pKa: ┄

CX LogP: 2.39

CX LogD: -3.70

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.41

Np Likeness Score: -0.62

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