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

ID: ALA2442885

PubChem CID: 72714339

Max Phase: Preclinical

Molecular Formula: C17H17NO5S2

Molecular Weight: 379.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H17NO5S2/c1-22-17(19)18-12-2-4-13(5-3-12)23-14-6-8-16(9-7-14)25(20,21)11-15-10-24-15/h2-9,15H,10-11H2,1H3,(H,18,19)

Standard InChI Key:  NKVKCTYTQNQNIH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    9.2839  -16.0802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8755  -15.3676    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.4626  -16.0776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8738  -14.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8727  -14.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875  -15.3911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3040  -14.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3011  -14.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5857  -13.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0141  -13.7320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7301  -14.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7299  -14.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4451  -15.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1590  -14.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1533  -14.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4374  -13.7236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5880  -14.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3046  -15.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7158  -16.0711    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.1250  -15.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1578  -15.3902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4436  -14.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7288  -15.3891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4443  -14.1521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146  -14.9760    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
M  END

Alternative Forms

1. Parent:

   

   ALA2442885

   methyl 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: 379.46

Molecular Weight (Monoisotopic): 379.0548

AlogP: 3.55

#Rotatable Bonds: 6

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: 13.25

CX Basic pKa: ┄

CX LogP: 2.60

CX LogD: 2.60

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.77

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