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

ID: ALA2206669

PubChem CID: 45379941

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-/m0/s1

Standard InChI Key:  BKJXHTXGHDYMGI-JYJNAYRXSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    7.3673   -3.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0579   -4.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5600   -4.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3716   -4.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6785   -3.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1745   -3.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4797   -2.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2888   -2.3809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5385   -1.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3029   -1.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7472   -3.0601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0083   -1.7208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5630   -3.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1218   -2.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3346   -3.7655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1692   -2.1975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9010   -2.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0773   -3.5732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5039   -2.2236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2828   -2.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8844   -1.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7121   -1.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9326   -0.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3254   -1.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4012   -0.4996    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8721   -3.8831    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 10 12  1  0
 11 13  1  0
 12 14  1  0
 13 14  1  0
 11 15  2  0
 10 16  1  0
 16 13  1  0
 14 17  1  6
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 10 25  1  6
 13 26  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2206669

   (1S,5S,6S)-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. 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]

Source

Source(1):

• Scientific Literature