(3S,4R)-8-fluoro-3-(2-fluoropropan-2-yl)-4-(2-phenylethynyl)-3,4-dihydro-2H-chromene

ID: ALA257721

PubChem CID: 44454584

Max Phase: Preclinical

Molecular Formula: C20H18F2O

Molecular Weight: 312.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(F)[C@@H]1COc2c(F)cccc2[C@@H]1C#Cc1ccccc1

Standard InChI:  InChI=1S/C20H18F2O/c1-20(2,22)17-13-23-19-16(9-6-10-18(19)21)15(17)12-11-14-7-4-3-5-8-14/h3-10,15,17H,13H2,1-2H3/t15-,17+/m0/s1

Standard InChI Key:  GFWDNTBNWINTTM-DOTOQJQBSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  1  0  0  0  0  0999 V2000
   -1.4894   -8.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4907   -9.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7785   -9.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7805   -7.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0632   -8.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0641   -9.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6487   -9.5135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3668   -9.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3677   -8.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6504   -7.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6501   -7.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6455   -6.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6409   -5.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3545   -4.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502   -4.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336   -3.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0800   -4.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0722   -4.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3597   -7.4484    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1465   -7.6406    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0830   -8.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926   -9.0918    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.4931   -7.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6777   -9.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7780  -10.3399    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  3  0
  2  3  1  0
 12 13  1  0
  3  6  2  0
 13 14  2  0
  1  2  2  0
 14 15  1  0
  5  4  2  0
 15 16  2  0
  4  1  1  0
 16 17  1  0
  5 10  1  0
 17 18  2  0
 18 13  1  0
  6  7  1  0
  9 19  1  1
  7  8  1  0
 10 20  1  1
  8  9  1  0
  9 21  1  0
  9 10  1  0
 21 22  1  0
  5  6  1  0
 21 23  1  0
 10 11  1  0
 21 24  1  0
  3 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA257721

   (3S,4S)-8-fluoro-3-(2-fluoropropan-2-yl)-4-(2-phenylethynyl)-3,4-dihydro-2H-chromene

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: 312.36

Molecular Weight (Monoisotopic): 312.1326

AlogP: 4.72

#Rotatable Bonds: 1

Polar Surface Area: 9.23

Molecular Species: NEUTRAL

HBA: 1

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 1

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.90

CX LogD: 4.90

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.69

Np Likeness Score: -0.25

References

1. Tyrrell E, Tesfa KH, Greenwood I, Mann A..  (2008)  The synthesis and biological evaluation of a range of novel functionalized benzopyrans as potential potassium channel activators.,  18  (3): [PMID:18191566] [10.1016/j.bmcl.2007.11.135]

Source

Source(1):

• Scientific Literature