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

ID: ALA606335

PubChem CID: 46229321

Max Phase: Preclinical

Molecular Formula: C16H20N2O5

Molecular Weight: 320.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H20N2O5/c19-8-4-7-17-15(20)13-14-16(21)18(10-12(22-13)23-14)9-11-5-2-1-3-6-11/h1-3,5-6,12-14,19H,4,7-10H2,(H,17,20)/t12-,13-,14-/m1/s1

Standard InChI Key:  AOMGFTCNWPKOCP-MGPQQGTHSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    6.2290  -13.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0250  -13.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6854  -13.6570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8900  -14.1154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7109  -14.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2690  -14.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0794  -15.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4329  -14.8850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4435  -15.7099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1420  -14.4634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6833  -14.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0653  -14.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6723  -14.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8469  -14.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539  -15.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8856  -16.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7145  -16.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1038  -15.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7734  -15.5094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8617  -14.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5708  -14.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0208  -12.3333    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0750  -15.8333    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2906  -14.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9997  -14.4267    0.0000 O   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
  2 22  1  1
  7 11  1  0
  7 23  1  1
  2 11  1  0
 21 24  1  0
  4  6  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA606335

   (1R,5R,6R)-3-benzyl-N-(3-hydroxypropyl)-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: 6

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: 13.12

CX Basic pKa: ┄

CX LogP: -0.41

CX LogD: -0.41

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.70

Np Likeness Score: -0.26

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