(2R*,4R*,6S*)-2-(4-Bromophenyl)tetrahydro-4-phenyl-6-(thiocyanatomethyl)-2H-pyran-4-ol

ID: ALA1094096

PubChem CID: 46220727

Max Phase: Preclinical

Molecular Formula: C19H18BrNO2S

Molecular Weight: 404.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CSC[C@@H]1C[C@@](O)(c2ccccc2)C[C@H](c2ccc(Br)cc2)O1

Standard InChI:  InChI=1S/C19H18BrNO2S/c20-16-8-6-14(7-9-16)18-11-19(22,15-4-2-1-3-5-15)10-17(23-18)12-24-13-21/h1-9,17-18,22H,10-12H2/t17-,18+,19-/m0/s1

Standard InChI Key:  PBQRRRNLLBVHCJ-OTWHNJEPSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -1.7125  -15.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7125  -16.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0005  -16.7708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2885  -16.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2885  -15.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0005  -15.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4208  -14.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0074  -13.6822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4270  -12.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2588  -12.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6690  -13.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2470  -14.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958  -14.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4254  -16.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4254  -16.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1405  -16.3646    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8543  -16.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667  -17.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1389  -16.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513  -16.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8496  -17.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1296  -18.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4201  -17.5974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5625  -18.0182    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
 12  7  1  0
  5  6  1  0
  6 13  1  1
  2 14  1  1
  6  7  1  0
  4 15  1  1
  1  2  1  0
 15 16  1  0
  7  8  2  0
 16 17  1  0
  1  6  1  0
 17 18  3  0
  8  9  1  0
 14 19  2  0
  2  3  1  0
 19 20  1  0
  9 10  2  0
 20 21  2  0
  3  4  1  0
 21 22  1  0
 10 11  1  0
 22 23  2  0
 23 14  1  0
  4  5  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094096

   (2R*,4R*,6S*)-2-(4-Bromophenyl)tetrahydro-4-phenyl-6-(thiocyanatomethyl)-2H-pyran-4-ol

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: 404.33

Molecular Weight (Monoisotopic): 403.0242

AlogP: 4.77

#Rotatable Bonds: 4

Polar Surface Area: 53.25

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.90

CX Basic pKa: ┄

CX LogP: 4.17

CX LogD: 4.17

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.75

Np Likeness Score: 0.24

References

1. Singh P, Bhardwaj A..  (2010)  Mono-, di-, and triaryl substituted tetrahydropyrans as cyclooxygenase-2 and tumor growth inhibitors. Synthesis and biological evaluation.,  53  (9): [PMID:20387815] [10.1021/jm1001327]

Source

Source(1):

• Scientific Literature