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

ID: ALA2206670

PubChem CID: 71463142

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)C1O[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-RUENRELNSA-N

Molfile:  

     RDKit          2D

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   15.6920   -4.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1942   -4.7671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0057   -4.6548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3127   -3.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8086   -3.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1139   -2.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9230   -2.3767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1726   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9371   -1.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3813   -3.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6425   -1.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1972   -3.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7560   -2.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9687   -3.7614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8033   -2.1934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5352   -2.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7115   -3.5691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1381   -2.2195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9170   -2.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0353   -0.4955    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.5063   -3.8790    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.0892   -3.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5227   -1.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3006   -2.1717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8671   -3.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0394   -4.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4728   -2.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 10 12  1  0
 11 13  1  0
 12 14  1  0
 13 14  1  0
 11 15  2  0
 10 16  1  0
 13 16  1  0
 14 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 10 21  1  1
 13 22  1  1
 20 23  1  6
 20 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2206670

   (1R,5R)-3-benzyl-N-[(2S)-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. Calugi C, Trabocchi A, De Bernardis F, Arancia S, Navarra P, Cauda R, Cassone A, Guarna A..  (2012)  Bicyclic peptidomimetics targeting secreted aspartic protease 2 (SAP2) from Candida albicans reveal a constrained inhibitory chemotype.,  20  (24): [PMID:23123016] [10.1016/j.bmc.2012.09.031]

Source

Source(1):

• Scientific Literature