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

ID: ALA2442888

PubChem CID: 72711065

Max Phase: Preclinical

Molecular Formula: C19H21NO5S2

Molecular Weight: 407.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)Nc1ccc(Oc2ccc(S(=O)(=O)CC3CS3)cc2)cc1

Standard InChI:  InChI=1S/C19H21NO5S2/c1-13(2)24-19(21)20-14-3-5-15(6-4-14)25-16-7-9-18(10-8-16)27(22,23)12-17-11-26-17/h3-10,13,17H,11-12H2,1-2H3,(H,20,21)

Standard InChI Key:  FNTWGXGOCVTLKR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   28.0682  -16.0967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6598  -15.3842    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   27.2470  -16.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6582  -14.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6570  -14.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3719  -15.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0883  -14.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0855  -14.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3701  -13.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7984  -13.7486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5145  -14.1584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5142  -14.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2294  -15.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9434  -14.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9376  -14.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2218  -13.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3724  -14.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0888  -15.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5001  -16.0876    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.9092  -15.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9422  -15.4068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2280  -14.9937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5132  -15.4057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2286  -14.1687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7990  -14.9925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0841  -15.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7996  -14.1675    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
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2442888

   propan-2-yl 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: 407.51

Molecular Weight (Monoisotopic): 407.0861

AlogP: 4.32

#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: 13.23

CX Basic pKa: ┄

CX LogP: 3.38

CX LogD: 3.38

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.69

Np Likeness Score: -1.04

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