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

ID: ALA2442890

PubChem CID: 72714092

Max Phase: Preclinical

Molecular Formula: C18H18O6S2

Molecular Weight: 394.47

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H18O6S2/c1-2-22-18(19)24-15-5-3-13(4-6-15)23-14-7-9-17(10-8-14)26(20,21)12-16-11-25-16/h3-10,16H,2,11-12H2,1H3

Standard InChI Key:  JOSPLESHDLLQSD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    9.6665   -6.3041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2582   -5.5914    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8453   -6.3015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2569   -4.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2558   -5.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9705   -5.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6869   -5.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6840   -4.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9686   -3.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3970   -3.9560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1128   -4.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1126   -5.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8279   -5.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5417   -5.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5359   -4.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8203   -3.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9706   -5.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6871   -5.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0983   -6.2950    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.5074   -5.5785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5408   -5.6141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268   -5.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1119   -5.6130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8275   -4.3761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978   -5.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6830   -5.6119    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:

   

   ALA2442890

   Ethyl [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: 394.47

Molecular Weight (Monoisotopic): 394.0545

AlogP: 3.90

#Rotatable Bonds: 7

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: 3.33

CX LogD: 3.33

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.40

Np Likeness Score: -0.64

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