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

ID: ALA5285886

Max Phase: Preclinical

Molecular Formula: C26H22N2O3

Molecular Weight: 410.47

Names and Identifiers

Canonical SMILES:  CN1O[C@@H](c2ccccc2)[C@@H]2CN(c3ccccc3)c3oc4ccccc4c(=O)c3[C@@H]21

Standard InChI:  InChI=1S/C26H22N2O3/c1-27-23-20(25(31-27)17-10-4-2-5-11-17)16-28(18-12-6-3-7-13-18)26-22(23)24(29)19-14-8-9-15-21(19)30-26/h2-15,20,23,25H,16H2,1H3/t20-,23-,25+/m1/s1

Standard InChI Key:  IUJKNNLRUJIZFV-XRODADMRSA-N

Molfile:  

 
     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
   -3.2693    0.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5548    1.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8429    0.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8429    0.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5530   -0.2890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2693    0.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1282    1.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4136    0.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4136    0.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1282   -0.2899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3009    1.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0156    0.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0156    0.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3009   -0.2899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3009   -1.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0156   -1.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0156   -2.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3009   -2.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4136   -2.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4136   -1.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4864    2.1819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2879    2.2628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6200    1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1282    2.1856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635    1.8496    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7711    0.6158    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0970    2.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0334    0.7869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8587    0.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2693    0.0738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8566   -0.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355   -0.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6190    0.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4452    1.5029    0.0000 H   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
  1  6  1  0
  6  5  2  0
  3  7  1  0
  8  7  1  0
  9  8  2  0
 10  9  1  0
  4 10  1  0
  8 11  1  0
 12 11  1  0
 13 12  1  0
 14 13  1  0
  9 14  1  0
 15 14  1  0
 15 16  1  0
 17 16  2  0
 18 17  1  0
 19 18  2  0
 15 20  2  0
 20 19  1  0
 11 21  1  0
 21 22  1  0
 23 22  1  0
 12 23  1  0
  7 24  2  0
 11 25  1  1
 12 26  1  1
 21 27  1  0
 23 28  1  1
 29 28  2  0
 30 29  1  0
 31 30  2  0
 32 31  1  0
 33 32  2  0
 28 33  1  0
 23 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5285886

   ---

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: 410.47

Molecular Weight (Monoisotopic): 410.1630

AlogP: 5.22

#Rotatable Bonds: 2

Polar Surface Area: 45.92

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 0.46

CX LogP: 4.87

CX LogD: 4.87

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.45

Np Likeness Score: -0.11

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