(1S,5R,7R)-3-Benzyl-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-carboxylic Acid [1-Hydroxymethyl-3(R)-methylbutyl]amide

ID: ALA600032

PubChem CID: 46228984

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+/m1/s1

Standard InChI Key:  YLFMGINTBAGZCH-VQHPVUNQSA-N

Molfile:  

     RDKit          2D

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   -1.5321    2.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2754    2.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4590    1.5858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9446    0.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1197    0.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6053    1.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7888    2.3901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7617    0.1975    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3026    0.1975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2840    1.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6965    0.8713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5321    3.5730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7030    1.5241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1990    1.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7602    2.0070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4422    0.6139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5645    1.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1256    2.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9299    2.2446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8077    1.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6120    0.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8552    0.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1731    1.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5215    0.8713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9340    0.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5215   -0.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6965   -0.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2840    0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  1  1  0
  5  8  1  6
  4  9  2  0
  3 10  1  0
 10 11  1  0
  1 12  1  1
  5 13  1  0
 13  1  1  0
  6 14  1  1
 14 15  1  0
 14 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  1
 20 21  1  0
 21 22  1  0
 21 23  1  0
 11 24  1  0
 11 28  2  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA600032

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

Source

Source(1):

• Scientific Literature