(1R,5S,7R)-3-benzyl-7-(4-(2-hydroxyethyl)piperazine-1-carbonyl)-6,8-dioxa-3-azabicyclo[3.2.1]octan-2-one

ID: ALA601919

PubChem CID: 46229297

Max Phase: Preclinical

Molecular Formula: C19H25N3O5

Molecular Weight: 375.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C([C@@H]1O[C@H]2CN(Cc3ccccc3)C(=O)[C@@H]1O2)N1CCN(CCO)CC1

Standard InChI:  InChI=1S/C19H25N3O5/c23-11-10-20-6-8-21(9-7-20)18(24)16-17-19(25)22(13-15(26-16)27-17)12-14-4-2-1-3-5-14/h1-5,15-17,23H,6-13H2/t15-,16-,17-/m1/s1

Standard InChI Key:  MNINKTQTTWKONY-BRWVUGGUSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   16.9540    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7500    2.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4104    2.3097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6150    1.8512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4359    1.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9940    1.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8044    0.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1579    1.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1685    0.2567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8670    1.5033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4083    1.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7903    1.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3973    1.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5719    1.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1789    0.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6106   -0.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4395   -0.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8288    0.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4984    0.4573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7458    3.6333    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.8000    0.1333    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.5896    1.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2966    1.5138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2902    2.3391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5707    2.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8574    2.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9979    2.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7161    2.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7235    1.5271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 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
 27 28  1  0
 24 27  1  0
  5  7  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA601919

   (1S,5R,6R)-3-benzyl-6-[4-(2-hydroxyethyl)piperazine-1-carbonyl]-7,8-dioxa-3-azabicyclo[3.2.1]octan-4-one

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: 375.43

Molecular Weight (Monoisotopic): 375.1794

AlogP: -0.72

#Rotatable Bonds: 5

Polar Surface Area: 82.55

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.06

CX Basic pKa: 6.63

CX LogP: -0.40

CX LogD: -0.47

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.73

Np Likeness Score: -0.66

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]

Source

Source(1):

• Scientific Literature