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

ID: ALA2442887

PubChem CID: 72711064

Max Phase: Preclinical

Molecular Formula: C19H21NO5S2

Molecular Weight: 407.51

Molecule Type: Small molecule

Names and Identifiers

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

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

Standard InChI Key:  KDYJIWZXMZGJQG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   35.9939  -16.9552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5855  -16.2426    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   35.1727  -16.9526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5837  -15.0258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5826  -15.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2974  -16.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0140  -15.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0111  -15.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2957  -14.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7240  -14.6070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4402  -15.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4399  -15.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1551  -16.2493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8691  -15.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8633  -15.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1475  -14.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2981  -15.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0145  -16.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4258  -16.9461    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   37.8349  -16.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8678  -16.2652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1536  -15.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4387  -16.2641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1542  -15.0272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7246  -15.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0097  -16.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2955  -15.8499    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:

   

   ALA2442887

   propyl 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: 4.33

#Rotatable Bonds: 8

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: 13.24

CX Basic pKa: ┄

CX LogP: 3.48

CX LogD: 3.48

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.66

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