(3aR,11bR)-8-chloro-1-methyl-5-phenyl-1,3,3a,4,5,11b-hexahydro-11H-chromeno[2,3-b]isoxazolo[3,4-d]pyridin-11-one

ID: ALA5281248

Max Phase: Preclinical

Molecular Formula: C20H17ClN2O3

Molecular Weight: 368.82

Names and Identifiers

Canonical SMILES:  CN1OC[C@@H]2CN(c3ccccc3)c3oc4cc(Cl)ccc4c(=O)c3[C@@H]21

Standard InChI:  InChI=1S/C20H17ClN2O3/c1-22-18-12(11-25-22)10-23(14-5-3-2-4-6-14)20-17(18)19(24)15-8-7-13(21)9-16(15)26-20/h2-9,12,18H,10-11H2,1H3/t12-,18+/m0/s1

Standard InChI Key:  LFRXQUIPQBAUCA-KPZWWZAWSA-N

Molfile:  

 
     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   -2.1630    0.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4484    1.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7364    0.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7364    0.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4466   -0.2890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1630    0.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0218   -0.2899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6927    0.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6927    0.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0218    1.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0218    2.1856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4074    1.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1220    0.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1220    0.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4074   -0.2899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4074   -1.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1220   -1.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1220   -2.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4074   -2.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6927   -2.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6928   -1.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7265    1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3944    2.2628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5928    2.1819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0093    2.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8775    0.6158    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429    1.8496    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8775   -0.2936    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  4  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  3 10  1  0
 10 11  2  0
  9 12  1  0
 13 12  1  0
 14 13  1  0
 15 14  1  0
  8 15  1  0
 16 15  1  0
 16 17  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 21 20  1  0
 16 21  2  0
 13 22  1  0
 22 23  1  0
 24 23  1  0
 12 24  1  0
 24 25  1  0
 13 26  1  1
 12 27  1  1
  6 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5281248

   ---

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: 368.82

Molecular Weight (Monoisotopic): 368.0928

AlogP: 4.13

#Rotatable Bonds: 1

Polar Surface Area: 45.92

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.69

CX LogD: 3.69

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.65

Np Likeness Score: -0.32

References

1. Goel P, Alam O, Naim MJ, Nawaz F, Iqbal M, Alam MI..  (2018)  Recent advancement of piperidine moiety in treatment of cancer- A review.,  157  [PMID:30114660] [10.1016/j.ejmech.2018.08.017]

Source

Source(1):

• Scientific Literature