(R/S)-2-(4-chlorophenyl)-N-(3-methoxy-4-(pent-2-ynyloxy)phenethyl)-2-(methylsulfonamido)acetamide

ID: ALA2287023

PubChem CID: 11155848

Max Phase: Preclinical

Molecular Formula: C23H27ClN2O5S

Molecular Weight: 479.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC#CCOc1ccc(CCNC(=O)C(NS(C)(=O)=O)c2ccc(Cl)cc2)cc1OC

Standard InChI:  InChI=1S/C23H27ClN2O5S/c1-4-5-6-15-31-20-12-7-17(16-21(20)30-2)13-14-25-23(27)22(26-32(3,28)29)18-8-10-19(24)11-9-18/h7-12,16,22,26H,4,13-15H2,1-3H3,(H,25,27)

Standard InChI Key:  KIDUMJRRQFPTMO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
   15.9889  -26.5216    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.6966  -26.1130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2812  -26.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5762  -27.2273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3934  -27.2273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4043  -26.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1120  -26.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4043  -27.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8197  -26.5216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1120  -25.2958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5274  -26.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2351  -26.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9428  -26.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6495  -26.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3567  -26.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3571  -25.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6444  -24.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9401  -25.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0642  -26.5266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0638  -27.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0643  -24.8901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7725  -25.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4797  -24.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1843  -24.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8901  -24.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6001  -24.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6944  -27.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6941  -28.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4023  -28.9715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1124  -28.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1092  -27.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4034  -29.7887    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  2  0
  1  5  2  0
  2  6  1  0
  6  7  1  0
  6  8  1  0
  7  9  1  0
  7 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 15 19  1  0
 19 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  3  0
 24 25  1  0
 25 26  1  0
  8 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31  8  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2287023

   2-(4-chlorophenyl)-2-(methanesulfonamido)-N-[2-(3-methoxy-4-pent-2-ynoxyphenyl)ethyl]acetamide

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: 479.00

Molecular Weight (Monoisotopic): 478.1329

AlogP: 3.09

#Rotatable Bonds: 10

Polar Surface Area: 93.73

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.37

CX Basic pKa: ┄

CX LogP: 3.33

CX LogD: 3.33

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.51

Np Likeness Score: -0.89

References

1. Lamberth C.  (2010)  Amino acid chemistry in crop protection,  66  (36): [10.1016/j.tet.2010.06.008]

Source

Source(1):

• Scientific Literature