ethyl 4-((1R,5S,7R)-3-benzyl-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-carbonyl)piperazine-1-carboxylate

ID: ALA589073

PubChem CID: 46229298

Max Phase: Preclinical

Molecular Formula: C20H25N3O6

Molecular Weight: 403.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)N1CCN(C(=O)[C@@H]2O[C@H]3CN(Cc4ccccc4)C(=O)[C@@H]2O3)CC1

Standard InChI:  InChI=1S/C20H25N3O6/c1-2-27-20(26)22-10-8-21(9-11-22)18(24)16-17-19(25)23(13-15(28-16)29-17)12-14-6-4-3-5-7-14/h3-7,15-17H,2,8-13H2,1H3/t15-,16-,17-/m1/s1

Standard InChI Key:  LEMKPDYSLPJBQO-BRWVUGGUSA-N

Molfile:  

     RDKit          2D

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    5.5244    2.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3203    2.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9807    1.8221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1855    1.3636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0063    0.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5644    0.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3747    0.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7281    0.5942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7387   -0.2308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4373    1.0157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9788    1.4249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3609    1.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9678    0.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1425    0.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7495   -0.1264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1812   -0.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0100   -0.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3993   -0.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0688   -0.0302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3163    3.1456    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3703   -0.3542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1597    0.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8667    1.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8604    1.8515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1408    2.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4277    1.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5679    2.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2861    1.8645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5604    3.0953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2936    1.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0116    0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
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  8  9  2  0
  6 19  2  0
  8 10  1  0
  2 20  1  1
  5  8  1  1
  7 21  1  1
 10 22  1  0
  2  3  1  0
  7 11  1  0
  2 11  1  0
  4  6  1  0
  4 12  1  0
 10 26  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
  1  2  1  0
 12 13  1  0
  5  7  1  0
 27 28  1  0
 27 29  2  0
 24 27  1  0
 13 14  2  0
 28 30  1  0
  6  7  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA589073

   ethyl 4-[(1S,5R,6R)-3-benzyl-4-oxo-7,8-dioxa-3-azabicyclo[3.2.1]octane-6-carbonyl]piperazine-1-carboxylate

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: 403.44

Molecular Weight (Monoisotopic): 403.1743

AlogP: 0.44

#Rotatable Bonds: 4

Polar Surface Area: 88.62

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.06

CX Basic pKa: ┄

CX LogP: 0.50

CX LogD: 0.50

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.72

Np Likeness Score: -0.65

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