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

ID: ALA591948

PubChem CID: 46229319

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-YLFCFFPRSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   16.6665   -8.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4625   -8.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1229   -9.0987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3275   -9.5571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1484   -9.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7065  -10.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5169  -10.4509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8704  -10.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8810  -11.1516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5795   -9.9050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1208   -9.4958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5028   -9.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1098  -10.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2844  -10.3227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8914  -11.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3231  -11.7513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1520  -11.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5413  -11.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2109  -10.9511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2992  -10.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0083   -9.8867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7281  -10.2900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4583   -7.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.5125  -11.2750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.3098  -11.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0295  -11.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0401  -12.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7386  -11.1149    0.0000 C   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
 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
  4 12  1  0
 25 26  1  0
  1  2  1  0
 26 27  1  0
 12 13  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA591948

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

3. 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