methyl (1R,2S,3S,5S)-3-(3,4-dichlorophenyl)-8-oxabicyclo[3.2.1]octane-2-carboxylate

ID: ALA5271116

Max Phase: Preclinical

Molecular Formula: C15H16Cl2O3

Molecular Weight: 315.20

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H]1[C@@H](c2ccc(Cl)c(Cl)c2)C[C@@H]2CC[C@H]1O2

Standard InChI:  InChI=1S/C15H16Cl2O3/c1-19-15(18)14-10(7-9-3-5-13(14)20-9)8-2-4-11(16)12(17)6-8/h2,4,6,9-10,13-14H,3,5,7H2,1H3/t9-,10+,13+,14-/m0/s1

Standard InChI Key:  DHXANQGCRAVCSQ-PJQZNRQZSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    1.6438   -1.7735    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2313   -1.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4068   -1.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0074   -0.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4052    0.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2277    0.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6404   -0.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4654   -0.3473    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8322   -0.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2323   -1.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0570   -1.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4921   -0.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4921   -0.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0570    0.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4654    1.0640    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4654   -0.3463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2323    0.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8322    1.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2323    1.7735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0570    1.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0074    1.0640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4654   -1.7567    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  3  1  0
  5  4  2  0
  6  5  1  0
  2  7  1  0
  7  6  2  0
  7  8  1  0
  9  4  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  6
 11 16  1  0
 16 14  1  0
  9 17  1  0
 17 14  1  0
 17 18  1  1
 19 18  1  0
 20 19  1  0
 21 18  2  0
 11 22  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5271116

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 315.20

Molecular Weight (Monoisotopic): 314.0476

AlogP: 3.82

#Rotatable Bonds: 2

Polar Surface Area: 35.53

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.65

CX LogD: 3.65

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.78

Np Likeness Score: 0.46

References

1. Wu YJ, Meanwell NA..  (2021)  Geminal Diheteroatomic Motifs: Some Applications of Acetals, Ketals, and Their Sulfur and Nitrogen Homologues in Medicinal Chemistry and Drug Design.,  64  (14.0): [PMID:34213340] [10.1021/acs.jmedchem.1c00790]

Source

Source(1):

• Scientific Literature