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

ID: ALA2442892

PubChem CID: 72714094

Max Phase: Preclinical

Molecular Formula: C19H20O6S2

Molecular Weight: 408.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)Oc1ccc(Oc2ccc(S(=O)(=O)CC3CS3)cc2)cc1

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

Standard InChI Key:  FWECVAAARPJXSH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   10.2919  -11.8043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8835  -11.0919    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.4706  -11.8017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8820   -9.8751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8808  -10.7025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5957  -11.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3122  -10.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3092   -9.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5938   -9.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0222   -9.4563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7382   -9.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7380  -10.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4532  -11.0985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1670  -10.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1613   -9.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4455   -9.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5960  -10.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3125  -11.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7237  -11.7954    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.1328  -11.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1660  -11.1145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4518  -10.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7371  -11.1133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4525   -9.8764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0229  -10.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3081  -11.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0236   -9.8752    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:

   

   ALA2442892

   Propan-2-yl [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: 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: 3.75

CX LogD: 3.75

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.38

Np Likeness Score: -0.57

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