(1R,5R,7R)-3-benzyl-7-(piperidine-1-carbonyl)-6,8-dioxa-3-azabicyclo[3.2.1]octan-2-one

ID: ALA589301

PubChem CID: 11359441

Max Phase: Preclinical

Molecular Formula: C18H22N2O4

Molecular Weight: 330.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C([C@@H]1O[C@H]2CN(Cc3ccccc3)C(=O)[C@@H]1O2)N1CCCCC1

Standard InChI:  InChI=1S/C18H22N2O4/c21-17(19-9-5-2-6-10-19)15-16-18(22)20(12-14(23-15)24-16)11-13-7-3-1-4-8-13/h1,3-4,7-8,14-16H,2,5-6,9-12H2/t14-,15-,16-/m1/s1

Standard InChI Key:  BKJXHTXGHDYMGI-BZUAXINKSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    1.9152    0.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1719    0.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9883   -0.5946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5027   -1.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3277   -1.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8420   -0.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6585    0.2097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9152   -0.5251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2892   -2.0365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6464   -0.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2075   -0.1734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8895   -1.5665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0118   -0.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5730    0.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3298    1.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5255    1.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9643    0.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9152    1.3927    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1840   -0.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0295   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8264   -1.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0400   -2.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4566   -3.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3403   -2.9553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5539   -2.1584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6856   -1.9829    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  1  1  0
  5  8  1  0
  8  1  1  0
  4  9  2  0
  6 10  1  1
 10 11  1  0
 10 12  2  0
 11 13  1  0
 17 11  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  1 18  1  1
  3 19  1  0
 19 20  1  0
 20 21  1  0
 20 25  2  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
  5 26  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA589301

   (1R,5R,6R)-3-benzyl-6-(piperidine-1-carbonyl)-7,8-dioxa-3-azabicyclo[3.2.1]octan-4-one

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: 330.38

Molecular Weight (Monoisotopic): 330.1580

AlogP: 1.15

#Rotatable Bonds: 3

Polar Surface Area: 59.08

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.07

CX Basic pKa: ┄

CX LogP: 1.30

CX LogD: 1.30

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.83

Np Likeness Score: -0.48

References

1. Trabocchi A, Mannino C, Machetti F, De Bernardis F, Arancia S, Cauda R, Cassone A, Guarna A..  (2010)  Identification of inhibitors of drug-resistant Candida albicans strains from a library of bicyclic peptidomimetic compounds.,  53  (6): [PMID:20184325] [10.1021/jm901734u]

2. Calugi C, Trabocchi A, De Bernardis F, Arancia S, Navarra P, Cauda R, Cassone A, Guarna A..  (2012)  Bicyclic peptidomimetics targeting secreted aspartic protease 2 (SAP2) from Candida albicans reveal a constrained inhibitory chemotype.,  20  (24): [PMID:23123016] [10.1016/j.bmc.2012.09.031]

3. Calugi C, Guarna A, Trabocchi A..  (2014)  Identification of constrained peptidomimetic chemotypes as HIV protease inhibitors.,  84  [PMID:25042102] [10.1016/j.ejmech.2014.07.049]

4. Innocenti R, Lenci E, Menchi G, Pupi A, Trabocchi A..  (2017)  Design and synthesis of bicyclic acetals as Beta Secretase (BACE1) inhibitors.,  25  (19): [PMID:28359674] [10.1016/j.bmc.2017.03.030]

5. Liu N, Tu J, Dong G, Wang Y, Sheng C..  (2018)  Emerging New Targets for the Treatment of Resistant Fungal Infections.,  61  (13): [PMID:29294275] [10.1021/acs.jmedchem.7b01413]

Source

Source(1):

• Scientific Literature