(2S*,4R*,6S*)-Tetrahydro-2-methyl-4-phenyl-6-(thiocyanatomethyl)-2H-pyran-4-ol

ID: ALA1096383

PubChem CID: 46223820

Max Phase: Preclinical

Molecular Formula: C14H17NO2S

Molecular Weight: 263.36

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H17NO2S/c1-11-7-14(16,12-5-3-2-4-6-12)8-13(17-11)9-18-10-15/h2-6,11,13,16H,7-9H2,1H3/t11-,13-,14+/m0/s1

Standard InChI Key:  XZRWEDLKBUWJEV-FPMFFAJLSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    3.9417    0.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417    0.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6537   -0.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3657    0.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3657    0.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6537    1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2333    1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6468    2.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2271    3.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3954    3.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9851    2.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4072    1.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0583    1.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2288   -0.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0796   -0.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7946    0.0188    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.5085   -0.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2208   -0.8042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  2  3  1  0
  9 10  2  0
  3  4  1  0
 10 11  1  0
  4  5  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA1096383

   [(2S,4R,6S)-4-hydroxy-6-methyl-4-phenyloxan-2-yl]methyl thiocyanate

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: 263.36

Molecular Weight (Monoisotopic): 263.0980

AlogP: 2.66

#Rotatable Bonds: 3

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: 13.91

CX Basic pKa: ┄

CX LogP: 2.03

CX LogD: 2.03

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.85

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