(1R,5R,7R)-3-benzyl-N-(2-hydroxyethyl)-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-carboxamide

ID: ALA600651

PubChem CID: 46229318

Max Phase: Preclinical

Molecular Formula: C15H18N2O5

Molecular Weight: 306.32

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H18N2O5/c18-7-6-16-14(19)12-13-15(20)17(9-11(21-12)22-13)8-10-4-2-1-3-5-10/h1-5,11-13,18H,6-9H2,(H,16,19)/t11-,12-,13-/m1/s1

Standard InChI Key:  BFGRVDLSWZETLP-JHJVBQTASA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    6.5498   -8.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3458   -8.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0062   -8.5612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2109   -9.0196    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0318   -9.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5898   -9.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4002   -9.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7537   -9.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7643  -10.6141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4629   -9.3675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -8.9583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3862   -9.0419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9931   -9.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1677   -9.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7747  -10.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2064  -11.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0353  -11.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4246  -10.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0942  -10.4136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1826   -9.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8917   -9.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6114   -9.7525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3417   -7.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3958  -10.7375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  6  1  0
  4 12  1  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
 10 20  1  0
  5  8  1  1
 20 21  1  0
  2  3  1  0
 21 22  1  0
  7 11  1  0
  2 23  1  1
  2 11  1  0
  7 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA600651

   (1R,5R,6R)-3-benzyl-N-(2-hydroxyethyl)-4-oxo-7,8-dioxa-3-azabicyclo[3.2.1]octane-6-carboxamide

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: 306.32

Molecular Weight (Monoisotopic): 306.1216

AlogP: -0.75

#Rotatable Bonds: 5

Polar Surface Area: 88.10

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.07

CX Basic pKa: ┄

CX LogP: -0.47

CX LogD: -0.47

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.75

Np Likeness Score: -0.30

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