(R)-2-Benzyloxycarbonylamino-3-(methoxy-phenyl-phosphinoyl)-propionic acid methyl ester

ID: ALA89851

PubChem CID: 44322715

Max Phase: Preclinical

Molecular Formula: C19H22NO6P

Molecular Weight: 391.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](CP(=O)(OC)c1ccccc1)NC(=O)OCc1ccccc1

Standard InChI:  InChI=1S/C19H22NO6P/c1-24-18(21)17(14-27(23,25-2)16-11-7-4-8-12-16)20-19(22)26-13-15-9-5-3-6-10-15/h3-12,17H,13-14H2,1-2H3,(H,20,22)/t17-,27?/m0/s1

Standard InChI Key:  KSCTWFNVFQFHTE-OIGLVOGNSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  1  0  0  0  0  0999 V2000
    4.1042  -12.5667    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667  -12.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8917  -13.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917  -13.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4042  -13.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667  -11.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042  -11.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292  -13.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0417  -13.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792  -11.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2667  -14.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792  -13.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417  -11.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6792  -14.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3042  -14.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417  -12.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292  -13.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792  -13.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2167  -11.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4542  -14.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7542  -15.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667  -13.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417  -14.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3792  -15.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0667  -13.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5292  -14.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667  -13.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5042  -12.6542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  2  4  1  1
  5  4  1  0
  6  2  1  0
  7  1  2  0
  8  1  1  0
  9  5  2  0
 10  6  2  0
 11  5  1  0
 12  1  1  0
 13  6  1  0
 14 11  1  0
 15 14  1  0
 16  8  2  0
 17  8  1  0
 18 12  1  0
 19 13  1  0
 20 15  1  0
 21 15  2  0
 22 16  1  0
 23 17  2  0
 24 21  1  0
 25 20  2  0
 26 24  2  0
 27 23  1  0
  2 28  1  6
 27 22  2  0
 26 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA89851

   (R)-2-Benzyloxycarbonylamino-3-(methoxy-phenyl-phosphinoyl)-propionic acid methyl ester

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: 391.36

Molecular Weight (Monoisotopic): 391.1185

AlogP: 2.70

#Rotatable Bonds: 8

Polar Surface Area: 90.93

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.15

CX Basic pKa: ┄

CX LogP: 2.93

CX LogD: 2.93

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.55

Np Likeness Score: -0.29

References

1. Ross FC, Botting NP, Leeson PD.  (1996)  Synthesis of phosphinic acid transition state analogues for the reaction catalysed by kynureninase,  6  (22): [10.1016/S0960-894X(96)00483-0]

Source

Source(1):

• Scientific Literature