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

ID: ALA2309082

PubChem CID: 45379942

Max Phase: Preclinical

Molecular Formula: C19H26N2O5

Molecular Weight: 362.43

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H26N2O5/c1-12(2)8-14(11-22)20-18(23)16-17-19(24)21(10-15(25-16)26-17)9-13-6-4-3-5-7-13/h3-7,12,14-17,22H,8-11H2,1-2H3,(H,20,23)/t14-,15-,16-,17-/m0/s1

Standard InChI Key:  YLFMGINTBAGZCH-QAETUUGQSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    0.6067   -1.6953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8916   -0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1050    0.2141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6424   -0.9458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2128    1.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6424    0.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6067    1.2313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7836    2.9851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9733    3.1418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8703    4.1761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8916    0.4997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9318   -1.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9158   -3.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2051   -3.9775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859   -5.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8773   -6.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5880   -5.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6072   -3.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6816    1.0997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0539   -1.9325    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6067    2.2313    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4441    5.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9317    5.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5308    6.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1047    8.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3745    9.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2944    8.2972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3893    6.8712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
  2  3  1  0
 10 22  1  0
  7 11  1  0
 22 23  1  0
  2 11  1  0
 22 24  1  1
  4  6  1  0
 24 25  1  0
  4 12  1  0
 25 26  1  0
  1  2  1  0
 25 27  1  0
 12 13  1  0
 23 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2309082

   (1S,5S,6S)-3-benzyl-N-[(1S)-1-(hydroxymethyl)-3-methyl-butyl]-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: 362.43

Molecular Weight (Monoisotopic): 362.1842

AlogP: 0.66

#Rotatable Bonds: 7

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: 12.96

CX Basic pKa: ┄

CX LogP: 1.20

CX LogD: 1.20

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.74

Np Likeness Score: -0.06

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. 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]

Source

Source(1):

• Scientific Literature