(1R,5S,7R)-3-benzyl-7-(thiomorpholine-4-carbonyl)-6,8-dioxa-3-azabicyclo[3.2.1]octan-2-one

ID: ALA589074

PubChem CID: 46229300

Max Phase: Preclinical

Molecular Formula: C17H20N2O4S

Molecular Weight: 348.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C([C@@H]1O[C@H]2CN(Cc3ccccc3)C(=O)[C@@H]1O2)N1CCSCC1

Standard InChI:  InChI=1S/C17H20N2O4S/c20-16(18-6-8-24-9-7-18)14-15-17(21)19(11-13(22-14)23-15)10-12-4-2-1-3-5-12/h1-5,13-15H,6-11H2/t13-,14-,15-/m1/s1

Standard InChI Key:  VOJVZLFJVXKZSY-RBSFLKMASA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   16.1165   -2.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9125   -1.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5729   -2.4820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7775   -2.9404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5984   -3.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1565   -3.6748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9669   -3.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3204   -3.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3310   -4.5349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0295   -3.2884    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5708   -2.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9528   -2.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5598   -3.6880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7344   -3.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3414   -4.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7731   -5.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6020   -5.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9913   -4.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6609   -4.3344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9083   -1.1583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.9625   -4.6583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.7521   -3.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4591   -3.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4527   -2.4525    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.7332   -2.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0199   -2.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
 12 13  1  0
  5  7  1  0
 13 14  2  0
  6  7  1  0
 14 15  1  0
  1  4  1  0
 15 16  2  0
 16 17  1  0
  3  5  1  0
 17 18  2  0
 18 13  1  0
  8  9  2  0
  6 19  2  0
  8 10  1  0
  2 20  1  1
  5  8  1  1
  7 21  1  1
 10 22  1  0
  2  3  1  0
  7 11  1  0
  2 11  1  0
  4  6  1  0
  4 12  1  0
 10 26  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA589074

   (1S,5R,6R)-3-benzyl-6-(thiomorpholine-4-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: 348.42

Molecular Weight (Monoisotopic): 348.1144

AlogP: 0.71

#Rotatable Bonds: 3

Polar Surface Area: 59.08

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.07

CX Basic pKa: ┄

CX LogP: 0.81

CX LogD: 0.81

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.81

Np Likeness Score: -0.78

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]

Source

Source(1):

• Scientific Literature