3-[3-Biphenyl-4-yl-2-(phosphonomethyl-amino)-propionylamino]-propionic acid

ID: ALA2112023

PubChem CID: 10024283

Max Phase: Preclinical

Molecular Formula: C19H23N2O6P

Molecular Weight: 406.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCNC(=O)[C@@H](Cc1ccc(-c2ccccc2)cc1)NCP(=O)(O)O

Standard InChI:  InChI=1S/C19H23N2O6P/c22-18(23)10-11-20-19(24)17(21-13-28(25,26)27)12-14-6-8-16(9-7-14)15-4-2-1-3-5-15/h1-9,17,21H,10-13H2,(H,20,24)(H,22,23)(H2,25,26,27)/t17-/m1/s1

Standard InChI Key:  MVRLTBIHUWUGAR-QGZVFWFLSA-N

Molfile:  

     RDKit          2D

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    1.0917   -8.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0583   -7.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3375   -8.0375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3750   -7.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -8.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708   -8.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -5.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -7.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0875   -8.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3750   -6.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -8.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8042   -7.6250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5958   -8.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708   -7.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -5.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8042   -5.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -6.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917   -6.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -8.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625   -7.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917   -5.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8042   -6.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -5.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250   -4.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -3.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -5.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -4.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  1  1  0
  4  3  1  0
  5  4  1  0
  6  9  1  0
  7  1  2  0
  8 18  2  0
  9 20  1  0
 10  2  2  0
  5 11  1  6
 12  6  2  0
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 14  1  1  0
 15  1  1  0
 16  8  1  0
 17 22  2  0
 18 23  1  0
 19 11  1  0
 20 13  1  0
 21  6  1  0
 22 19  1  0
 23 19  2  0
 24 16  2  0
 25 16  1  0
 26 25  2  0
 27 24  1  0
 28 26  1  0
  8 17  1  0
 28 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2112023

   3-[[(2R)-3-(4-phenylphenyl)-2-(phosphonomethylamino)propanoyl]amino]propanoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 406.38

Molecular Weight (Monoisotopic): 406.1294

AlogP: 1.58

#Rotatable Bonds: 10

Polar Surface Area: 135.96

Molecular Species: ACID

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -0.58

CX Basic pKa: 6.41

CX LogP: -0.10

CX LogD: -4.04

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.38

Np Likeness Score: -0.16

References

1. De Lombaert S, Erion MD, Tan J, Blanchard L, el-Chehabi L, Ghai RD, Sakane Y, Berry C, Trapani AJ..  (1994)  N-Phosphonomethyl dipeptides and their phosphonate prodrugs, a new generation of neutral endopeptidase (NEP, EC 3.4.24.11) inhibitors.,  37  (4): [PMID:8120868] [10.1021/jm00030a009]

Source

Source(1):

• Scientific Literature