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

ID: ALA592182

PubChem CID: 46229320

Max Phase: Preclinical

Molecular Formula: C16H20N2O5

Molecular Weight: 320.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H20N2O5/c1-10(9-19)17-15(20)13-14-16(21)18(8-12(22-13)23-14)7-11-5-3-2-4-6-11/h2-6,10,12-14,19H,7-9H2,1H3,(H,17,20)/t10-,12+,13+,14+/m0/s1

Standard InChI Key:  FNJDYKVKCOWDKN-IGHBBLSQSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -2.8668  -13.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708  -13.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4105  -14.0528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2058  -14.5113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3849  -14.8764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8269  -15.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0164  -15.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6629  -15.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523  -16.1058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0462  -14.8592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4125  -14.4500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0305  -14.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4236  -15.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2489  -15.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6419  -16.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2102  -16.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3814  -16.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9921  -15.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3224  -15.9052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4750  -14.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1947  -15.2442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0750  -12.7292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0208  -16.2292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7765  -16.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  4  6  1  0
 20 25  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA592182

   (1R,5R,6R)-3-benzyl-N-[(1S)-2-hydroxy-1-methyl-ethyl]-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: 320.35

Molecular Weight (Monoisotopic): 320.1372

AlogP: -0.36

#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: 12.95

CX Basic pKa: ┄

CX LogP: -0.05

CX LogD: -0.05

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.77

Np Likeness Score: -0.28

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

Source

Source(1):

• Scientific Literature