Propyl(4-(4-((Thiiran-2-ylmethyl)sulfonyl)phenoxy)phenyl)carbonate

ID: ALA2442891

PubChem CID: 72714093

Max Phase: Preclinical

Molecular Formula: C19H20O6S2

Molecular Weight: 408.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCOC(=O)Oc1ccc(Oc2ccc(S(=O)(=O)CC3CS3)cc2)cc1

Standard InChI:  InChI=1S/C19H20O6S2/c1-2-11-23-19(20)25-16-5-3-14(4-6-16)24-15-7-9-18(10-8-15)27(21,22)13-17-12-26-17/h3-10,17H,2,11-13H2,1H3

Standard InChI Key:  NDWDLJQCZNKAHG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   10.0547   -9.1672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6463   -8.4546    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.2335   -9.1645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6446   -7.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6435   -8.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3583   -8.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0748   -8.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0720   -7.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3566   -6.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7849   -6.8190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5010   -7.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5007   -8.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2159   -8.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9299   -8.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9242   -7.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2083   -6.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3589   -8.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0753   -8.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4866   -9.1581    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.8957   -8.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9287   -8.4772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145   -8.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4996   -8.4761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151   -7.2391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7855   -8.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706   -8.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3564   -8.0618    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
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2442891

   Propyl [4-[4-(thiiran-2-ylmethylsulfonyl)phenoxy]phenyl] carbonate

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: 408.50

Molecular Weight (Monoisotopic): 408.0701

AlogP: 4.29

#Rotatable Bonds: 8

Polar Surface Area: 78.90

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.85

CX LogD: 3.85

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.37

Np Likeness Score: -0.62

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