(2R*,3S*,4R*,6S*)-2-(4-Bromophenyl)-6-((ethylthio)methyl)-tetrahydro-3,4-diphenyl-2H-pyran-4-ol)

ID: ALA1096725

PubChem CID: 46220945

Max Phase: Preclinical

Molecular Formula: C26H27BrO2S

Molecular Weight: 483.47

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C26H27BrO2S/c1-2-30-18-23-17-26(28,21-11-7-4-8-12-21)24(19-9-5-3-6-10-19)25(29-23)20-13-15-22(27)16-14-20/h3-16,23-25,28H,2,17-18H2,1H3/t23-,24-,25-,26-/m0/s1

Standard InChI Key:  GJKDCSBFEHBUOJ-CQJMVLFOSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   16.0083   -9.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0083  -10.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7204  -10.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4324  -10.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4324   -9.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7204   -8.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3000   -8.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7134   -7.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2938   -6.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4621   -6.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0518   -7.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4738   -8.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1250   -8.2083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2954  -10.5807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1462  -10.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8613  -10.1687    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.5752  -10.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2903  -10.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5820  -10.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8696  -10.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8712  -11.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5912  -11.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3007  -11.4016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1583  -11.8223    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   15.2951   -8.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2940   -8.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5792   -7.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8649   -8.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8700   -8.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5854   -9.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  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  1  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
 11 12  2  0
 12  7  1  0
 25 26  2  0
  5  6  1  0
 26 27  1  0
  6 13  1  6
 27 28  2  0
 28 29  1  0
  2 14  1  1
 29 30  2  0
 30 25  1  0
  1 25  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1096725

   (2R,3S,4R,6S)-2-(4-bromophenyl)-6-(ethylsulfanylmethyl)-3,4-diphenyloxan-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: 483.47

Molecular Weight (Monoisotopic): 482.0915

AlogP: 6.70

#Rotatable Bonds: 6

Polar Surface Area: 29.46

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.60

CX Basic pKa: ┄

CX LogP: 6.36

CX LogD: 6.36

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.42

Np Likeness Score: 0.28

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