Diethyl(4-chloro-2-nitrophenylamino)(4-hydroxy phenyl)methylphosphonate

ID: ALA1762131

PubChem CID: 54582433

Max Phase: Preclinical

Molecular Formula: C17H20ClN2O6P

Molecular Weight: 414.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOP(=O)(OCC)C(Nc1ccc(Cl)cc1[N+](=O)[O-])c1ccc(O)cc1

Standard InChI:  InChI=1S/C17H20ClN2O6P/c1-3-25-27(24,26-4-2)17(12-5-8-14(21)9-6-12)19-15-10-7-13(18)11-16(15)20(22)23/h5-11,17,19,21H,3-4H2,1-2H3

Standard InChI Key:  JPIUBJORAABACB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   -1.9375    0.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2230    0.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5086    0.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5111   -0.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2025   -0.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9180   -0.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9153    0.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2011    0.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6520    0.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6470    1.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3606    1.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0761    1.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0734    0.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3592    0.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9375   -0.5833    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.6330   -0.9958    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1962    1.4806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5196    1.8909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9094    1.8953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7375   -0.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7250   -1.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125   -0.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3081   -1.9586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -2.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6964   -1.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1286   -1.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7911    1.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
 13 14  2  0
 14  9  1  0
  3  4  2  0
  1 15  1  0
  7  8  2  0
  6 16  1  0
  8  3  1  0
  1  9  1  0
 17 18  2  0
 17 19  1  0
  8 17  1  0
  4  5  1  0
 15 20  2  0
  9 10  2  0
 15 21  1  0
  2  3  1  0
 15 22  1  0
 10 11  1  0
 21 23  1  0
  5  6  2  0
 23 24  1  0
 11 12  2  0
 22 25  1  0
  1  2  1  0
 25 26  1  0
 12 13  1  0
 12 27  1  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1762131

   4-[(4-Chloro-2-nitroanilino)-diethoxyphosphorylmethyl]phenol

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: 414.78

Molecular Weight (Monoisotopic): 414.0748

AlogP: 5.33

#Rotatable Bonds: 9

Polar Surface Area: 110.93

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.06

CX Basic pKa: ┄

CX LogP: 4.91

CX LogD: 4.90

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.32

Np Likeness Score: -0.89

References

1. Dake SA, Raut DS, Kharat KR, Mhaske RS, Deshmukh SU, Pawar RP..  (2011)  Ionic liquid promoted synthesis, antibacterial and in vitro antiproliferative activity of novel α-aminophosphonate derivatives.,  21  (8): [PMID:21398120] [10.1016/j.bmcl.2011.02.039]

Source

Source(1):

• Scientific Literature