4-(4-(2,3-Dimethylphenyl)piperazine-1-carboxamido)-3-fluorophenyl sulfamate

ID: ALA4550166

PubChem CID: 155550484

Max Phase: Preclinical

Molecular Formula: C19H23FN4O4S

Molecular Weight: 422.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cccc(N2CCN(C(=O)Nc3ccc(OS(N)(=O)=O)cc3F)CC2)c1C

Standard InChI:  InChI=1S/C19H23FN4O4S/c1-13-4-3-5-18(14(13)2)23-8-10-24(11-9-23)19(25)22-17-7-6-15(12-16(17)20)28-29(21,26)27/h3-7,12H,8-11H2,1-2H3,(H,22,25)(H2,21,26,27)

Standard InChI Key:  FZZDTWJPBNLKFL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   19.6539  -15.2419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2494  -14.5361    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.8404  -15.2393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4208  -14.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4197  -15.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1277  -15.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8374  -15.3675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8346  -14.5448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1259  -14.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7116  -15.7760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0043  -15.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2962  -15.7749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0049  -14.5497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5916  -15.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8857  -15.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8808  -16.5826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5880  -16.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3001  -16.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5407  -14.1336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9561  -14.1283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1713  -16.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4661  -16.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7570  -16.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7529  -17.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4637  -18.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1698  -17.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7130  -14.1400    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.8770  -18.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4628  -19.0248    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 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 12 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  8 19  1  0
 19  2  1  0
  2 20  1  0
 16 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  4 27  1  0
 26 28  1  0
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4550166

   ---

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: 422.48

Molecular Weight (Monoisotopic): 422.1424

AlogP: 2.38

#Rotatable Bonds: 4

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: 10.53

CX Basic pKa: 3.78

CX LogP: 2.88

CX LogD: 2.88

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.79

Np Likeness Score: -1.93

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]

Source

Source(1):

• Scientific Literature