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

ID: ALA1095084

PubChem CID: 46224075

Max Phase: Preclinical

Molecular Formula: C20H23BrO2S

Molecular Weight: 407.37

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H23BrO2S/c1-2-24-14-18-12-20(22,16-6-4-3-5-7-16)13-19(23-18)15-8-10-17(21)11-9-15/h3-11,18-19,22H,2,12-14H2,1H3/t18-,19+,20-/m0/s1

Standard InChI Key:  ZEBVEZWCKJNDFY-ZCNNSNEGSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   15.3042   -9.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3042  -10.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0162  -10.6333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7282  -10.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7282   -9.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0162   -8.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5958   -8.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0093   -7.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5896   -6.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7579   -6.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3476   -7.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7697   -8.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4208   -8.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5913  -10.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4421  -10.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1571  -10.2271    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.8710  -10.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5861  -10.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8778  -10.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1654  -10.6401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1670  -11.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8871  -11.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5965  -11.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4542  -11.8807    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  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
M  END

Alternative Forms

1. Parent:

   

   ALA1095084

   (2R*,4R*,6S*)-2-(4-Bromophenyl)-6-((ethylthio)methyl)tetrahydro-4-phenyl-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: 407.37

Molecular Weight (Monoisotopic): 406.0602

AlogP: 5.31

#Rotatable Bonds: 5

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: 13.90

CX Basic pKa: ┄

CX LogP: 4.75

CX LogD: 4.75

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.73

Np Likeness Score: 0.13

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