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

ID: ALA85072

Cas Number: 185521-30-6

PubChem CID: 44322939

Max Phase: Preclinical

Molecular Formula: C18H20NO6P

Molecular Weight: 377.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COP(=O)(C[C@H](NC(=O)OCc1ccccc1)C(=O)O)c1ccccc1

Standard InChI:  InChI=1S/C18H20NO6P/c1-24-26(23,15-10-6-3-7-11-15)13-16(17(20)21)19-18(22)25-12-14-8-4-2-5-9-14/h2-11,16H,12-13H2,1H3,(H,19,22)(H,20,21)/t16-,26?/m0/s1

Standard InChI Key:  AHMPRMXUEOOKTP-AJWVYOOVSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  1  0  0  0  0  0999 V2000
    4.0917   -2.3042    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.6500   -2.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8750   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8792   -3.0750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3917   -3.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6500   -1.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0875   -1.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3125   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0292   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8667   -0.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2542   -4.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -3.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4250   -0.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -4.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2875   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3125   -3.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667   -3.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4417   -3.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7417   -4.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3625   -4.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0542   -3.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5167   -4.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500   -3.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917   -2.3917    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  1  0
 17  8  2  0
 18 12  1  0
 19 15  1  0
 20 15  2  0
 21 17  1  0
 22 16  2  0
 23 20  1  0
 24 19  2  0
 25 23  2  0
 26 21  2  0
  2 27  1  6
 26 22  1  0
 25 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA85072

   N-[(Benzyloxy)carbonyl]-3-[methoxy(phenyl)phosphoryl]-L-alanine

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: 377.33

Molecular Weight (Monoisotopic): 377.1028

AlogP: 2.62

#Rotatable Bonds: 8

Polar Surface Area: 101.93

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.69

CX Basic pKa: ┄

CX LogP: 2.90

CX LogD: -0.50

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: -0.22

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