4-(4-Octylpiperazine-1-carboxamido)phenyl sulfamate

ID: ALA4560198

PubChem CID: 155558253

Max Phase: Preclinical

Molecular Formula: C19H32N4O4S

Molecular Weight: 412.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCCCN1CCN(C(=O)Nc2ccc(OS(N)(=O)=O)cc2)CC1

Standard InChI:  InChI=1S/C19H32N4O4S/c1-2-3-4-5-6-7-12-22-13-15-23(16-14-22)19(24)21-17-8-10-18(11-9-17)27-28(20,25)26/h8-11H,2-7,12-16H2,1H3,(H,21,24)(H2,20,25,26)

Standard InChI Key:  LQZYRLUTMVYEGJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   27.4956  -22.1756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9083  -22.8855    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.3167  -22.1731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.3267  -22.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3255  -22.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0336  -23.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7432  -22.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7404  -22.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0318  -21.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6175  -23.2958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2021  -23.2947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4466  -21.6534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1558  -22.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8620  -21.6481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1589  -22.8765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.5698  -22.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2739  -21.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2750  -20.8314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.5659  -20.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8557  -20.8327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9827  -20.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6904  -20.8314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6904  -21.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3981  -22.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1058  -21.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8135  -22.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5213  -21.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2290  -22.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  5 10  1  0
 10  2  1  0
  2 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 14 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4560198

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 412.56

Molecular Weight (Monoisotopic): 412.2144

AlogP: 2.78

#Rotatable Bonds: 10

Polar Surface Area: 104.97

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.75

CX Basic pKa: 7.63

CX LogP: 2.92

CX LogD: 2.49

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: -1.33

References

1. Moi D, Foster PA, Rimmer LG, Jaffri A, Deplano A, Balboni G, Onnis V, Potter BVL..  (2019)  Synthesis and in vitro evaluation of piperazinyl-ureido sulfamates as steroid sulfatase inhibitors.,  182  [PMID:31422224] [10.1016/j.ejmech.2019.111614]

2. Nocentini A,Moi D,Deplano A,Osman SM,AlOthman ZA,Balboni G,Supuran CT,Onnis V.  (2020)  Sulfonamide/sulfamate switch with a series of piperazinylureido derivatives: Synthesis, kinetic and in silico evaluation as carbonic anhydrase isoforms I, II, IV, and IX inhibitors.,  186  [PMID:31784185] [10.1016/j.ejmech.2019.111896]

Source

Source(1):

• Scientific Literature