Phosphoric acid mono-{4-[1-(4-tert-butyl-benzyl)-2-oxo-azepan-3-ylcarbamoyl]-phenyl} ester

ID: ALA1160752

PubChem CID: 44330291

Max Phase: Preclinical

Molecular Formula: C24H31N2O6P

Molecular Weight: 474.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(CN2CCCC[C@H](NC(=O)c3ccc(OP(=O)(O)O)cc3)C2=O)cc1

Standard InChI:  InChI=1S/C24H31N2O6P/c1-24(2,3)19-11-7-17(8-12-19)16-26-15-5-4-6-21(23(26)28)25-22(27)18-9-13-20(14-10-18)32-33(29,30)31/h7-14,21H,4-6,15-16H2,1-3H3,(H,25,27)(H2,29,30,31)/t21-/m0/s1

Standard InChI Key:  DYWKARYBKVIDMT-NRFANRHFSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    2.2417   -6.0542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5792   -8.4542    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167   -6.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1417   -5.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -6.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167   -5.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -6.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417   -6.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1542   -7.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3917   -8.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7917   -7.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3292   -9.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1125   -7.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5208   -5.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7250   -5.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1750   -5.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6042   -6.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7292   -7.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5125   -6.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -5.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8625   -6.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417   -7.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -5.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792   -7.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542   -5.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3750   -7.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2542   -6.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125   -5.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333   -4.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083   -6.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083   -5.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125   -4.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -4.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 11  1  0
  3  1  1  0
  4  5  1  0
  6  5  1  6
  6  3  1  0
  7  1  1  0
  8  4  1  0
  9  2  1  0
 10  2  1  0
 11 22  1  0
 12  2  2  0
 13  3  2  0
 14 15  1  0
 15 20  2  0
 16  4  2  0
 17  8  1  0
 18  8  2  0
 19 24  2  0
 20 25  1  0
 21  7  1  0
 22 26  2  0
 23  1  1  0
 24 21  1  0
 25 21  2  0
 26 18  1  0
 27 17  2  0
 28  6  1  0
 29 14  1  0
 30 14  1  0
 31 14  1  0
 32 23  1  0
 33 32  1  0
 33 28  1  0
 19 15  1  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1160752

   [4-[[(3S)-1-[(4-tert-butylphenyl)methyl]-2-oxoazepan-3-yl]carbamoyl]phenyl] dihydrogen phosphate

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: 474.49

Molecular Weight (Monoisotopic): 474.1920

AlogP: 3.77

#Rotatable Bonds: 6

Polar Surface Area: 116.17

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.78

CX Basic pKa: ┄

CX LogP: 3.54

CX LogD: 0.43

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.55

Np Likeness Score: -0.60

References

1. Lange G, Lesuisse D, Deprez P, Schoot B, Loenze P, Bénard D, Marquette JP, Broto P, Sarubbi E, Mandine E..  (2002)  Principles governing the binding of a class of non-peptidic inhibitors to the SH2 domain of src studied by X-ray analysis.,  45  (14): [PMID:12086479] [10.1021/jm0110800]

Source

Source(1):

• Scientific Literature