Ethyl(4-(4-((Thiiran-2-ylmethyl)sulfonyl)phenoxy)phenyl)carbamate

ID: ALA2442886

PubChem CID: 72711063

Max Phase: Preclinical

Molecular Formula: C18H19NO5S2

Molecular Weight: 393.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)Nc1ccc(Oc2ccc(S(=O)(=O)CC3CS3)cc2)cc1

Standard InChI:  InChI=1S/C18H19NO5S2/c1-2-23-18(20)19-13-3-5-14(6-4-13)24-15-7-9-17(10-8-15)26(21,22)12-16-11-25-16/h3-10,16H,2,11-12H2,1H3,(H,19,20)

Standard InChI Key:  LJRIZWAWUQHHTF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   21.3221  -16.4843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9138  -15.7718    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.5009  -16.4817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9121  -14.5551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9109  -15.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6258  -15.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3422  -15.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3394  -14.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6240  -14.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0524  -14.1362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7684  -14.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7682  -15.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4834  -15.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1973  -15.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1915  -14.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4757  -14.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6263  -15.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3427  -15.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7541  -16.4753    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.1632  -15.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1961  -15.7944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4819  -15.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7670  -15.7932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4826  -14.5563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0528  -15.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3380  -15.7921    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
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 14  2  1  0
  2 17  1  0
 17 18  1  0
 19 18  1  0
 20 19  1  0
 18 20  1  0
  5 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2442886

   ethyl N-[4-[4-(thiiran-2-ylmethylsulfonyl)phenoxy]phenyl]carbamate

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: 393.49

Molecular Weight (Monoisotopic): 393.0705

AlogP: 3.94

#Rotatable Bonds: 7

Polar Surface Area: 81.70

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.24

CX Basic pKa: ┄

CX LogP: 2.96

CX LogD: 2.96

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: -1.09

References

1. Gooyit M, Song W, Mahasenan KV, Lichtenwalter K, Suckow MA, Schroeder VA, Wolter WR, Mobashery S, Chang M..  (2013)  O-phenyl carbamate and phenyl urea thiiranes as selective matrix metalloproteinase-2 inhibitors that cross the blood-brain barrier.,  56  (20): [PMID:24028490] [10.1021/jm401217d]

Source

Source(1):

• Scientific Literature