1-[(7S,8R)-7-hydroxy-6,6-dimethyl-7,8-dihydropyrano[2,3-f][2,1,3]benzoxadiazol-8-yl]piperidin-2-one

ID: ALA5285684

Max Phase: Preclinical

Molecular Formula: C16H19N3O4

Molecular Weight: 317.35

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2cc3nonc3cc2[C@@H](N2CCCCC2=O)[C@@H]1O

Standard InChI:  InChI=1S/C16H19N3O4/c1-16(2)15(21)14(19-6-4-3-5-13(19)20)9-7-10-11(18-23-17-10)8-12(9)22-16/h7-8,14-15,21H,3-6H2,1-2H3/t14-,15+/m1/s1

Standard InChI Key:  KMXPHBJUGYLXDM-CABCVRRESA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    1.9396   -2.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6574   -1.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6574   -0.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9430   -0.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2285   -0.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4858   -0.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2002   -0.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9850   -0.3886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4699   -1.0561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9850   -1.7235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2002   -1.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4858   -1.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2285   -1.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9430   -1.8811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9430    0.5937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6574    1.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6574    1.8313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9430    2.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2285    1.8313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2285    1.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4858    0.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3719   -0.2311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4699   -1.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  7 11  1  0
 11 12  1  0
 12 13  2  0
  5 13  1  0
 13 14  1  0
  2 14  1  0
  4 15  1  1
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 15 20  1  0
 20 21  2  0
  3 22  1  6
  2 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5285684

   ---

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: 317.35

Molecular Weight (Monoisotopic): 317.1376

AlogP: 1.81

#Rotatable Bonds: 1

Polar Surface Area: 88.69

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.24

CX Basic pKa: ┄

CX LogP: 0.96

CX LogD: 0.96

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.86

Np Likeness Score: 0.37

References

1. Mancini RS, Barden CJ, Weaver DF, Reed MA..  (2021)  Furazans in Medicinal Chemistry.,  64  (4.0): [PMID:33569941] [10.1021/acs.jmedchem.0c01901]

Source

Source(1):

• Scientific Literature