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

ID: ALA1095094

PubChem CID: 46220946

Max Phase: Preclinical

Molecular Formula: C25H22BrNO2S

Molecular Weight: 480.43

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H22BrNO2S/c26-21-13-11-19(12-14-21)24-23(18-7-3-1-4-8-18)25(28,20-9-5-2-6-10-20)15-22(29-24)16-30-17-27/h1-14,22-24,28H,15-16H2/t22-,23-,24-,25-/m0/s1

Standard InChI Key:  VAARSVSQTNZNIE-QORCZRPOSA-N

Molfile:  

     RDKit          2D

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   -2.3208  -16.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6088  -17.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8968  -15.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6088  -15.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0292  -14.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6157  -14.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0354  -13.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671  -13.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2774  -14.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2042  -14.8458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1829  -17.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5321  -16.8062    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460  -17.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9583  -17.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7472  -16.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4596  -17.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4580  -18.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7379  -18.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0285  -18.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1708  -18.4598    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.0341  -15.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0352  -14.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7500  -14.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4642  -14.7491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4592  -15.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7437  -15.9849    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
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  7  8  2  0
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 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
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  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:

   

   ALA1095094

   (2R*,3S*,4R*,6S*)-2-(4-Bromophenyl)tetrahydro-3,4-diphenyl-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: 480.43

Molecular Weight (Monoisotopic): 479.0555

AlogP: 6.16

#Rotatable Bonds: 5

Polar Surface Area: 53.25

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.60

CX Basic pKa: ┄

CX LogP: 5.78

CX LogD: 5.78

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.44

Np Likeness Score: 0.37

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