5-chloro-2-(1-(3-ethoxy-4-methoxybenzyl)piperidin-4-ylamino)benzo[d]oxazole-6-sulfonamide

ID: ALA1078240

PubChem CID: 46882664

Max Phase: Preclinical

Molecular Formula: C22H27ClN4O5S

Molecular Weight: 495.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1cc(CN2CCC(Nc3nc4cc(Cl)c(S(N)(=O)=O)cc4o3)CC2)ccc1OC

Standard InChI:  InChI=1S/C22H27ClN4O5S/c1-3-31-20-10-14(4-5-18(20)30-2)13-27-8-6-15(7-9-27)25-22-26-17-11-16(23)21(33(24,28)29)12-19(17)32-22/h4-5,10-12,15H,3,6-9,13H2,1-2H3,(H,25,26)(H2,24,28,29)

Standard InChI Key:  GWSJPOPJXLJSLF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -3.0606    2.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0619    1.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3449    0.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3469    2.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6340    2.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6336    1.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8476    0.9539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642    1.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8488    2.2855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4601    1.6211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8730    0.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4617    0.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8708   -0.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6954   -0.5195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1092    0.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6984    0.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1053   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9296   -1.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3413   -1.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1648   -1.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5755   -1.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1653   -0.5234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3387   -0.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5769    0.1889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4012    0.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8128    0.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3998   -1.2406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8153   -1.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7743    0.7903    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727    2.4407    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4891    2.0283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3658    3.1598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1901    3.1598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
 15 16  1  0
  6  7  1  0
 14 17  1  0
  7  8  2  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
  9  5  1  0
 19 20  1  0
  4  1  1  0
 20 21  2  0
  8 10  1  0
 21 22  1  0
  5  6  1  0
 22 23  2  0
 23 18  1  0
 10 11  1  0
 22 24  1  0
 11 12  1  0
 24 25  1  0
 25 26  1  0
  2  3  1  0
 21 27  1  0
  3  6  2  0
 27 28  1  0
  1  2  2  0
  2 29  1  0
  5  4  2  0
  1 30  1  0
 11 16  1  0
 30 31  1  0
 12 13  1  0
 30 32  2  0
 13 14  1  0
 30 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1078240

   5-Chloro-2-(1-(3-ethoxy-4-methoxybenzyl)piperidin-4-ylamino)benzo[d]oxazole-6-sulfonamide

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: 495.00

Molecular Weight (Monoisotopic): 494.1391

AlogP: 3.61

#Rotatable Bonds: 8

Polar Surface Area: 119.92

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.76

CX Basic pKa: 7.52

CX LogP: 2.29

CX LogD: 2.08

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.49

Np Likeness Score: -1.64

References

1. Martin RE, Mohr P, Maerki HP, Guba W, Kuratli C, Gavelle O, Binggeli A, Bendels S, Alvarez-Sánchez R, Alker A, Polonchuk L, Christ AD..  (2009)  Benzoxazole piperidines as selective and potent somatostatin receptor subtype 5 antagonists.,  19  (21): [PMID:19786348] [10.1016/j.bmcl.2009.09.024]

Source

Source(1):

• Scientific Literature