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

ID: ALA2206671

PubChem CID: 71455975

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-KWEKYREISA-N

Molfile:  

     RDKit          2D

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   24.8339   -3.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3360   -4.6392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1475   -4.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4545   -3.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9504   -3.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2557   -2.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0648   -2.2488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3144   -1.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.5231   -2.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7843   -1.5888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3390   -2.9945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8978   -2.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1106   -3.6335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9451   -2.0655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6770   -2.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8533   -3.4411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.2799   -2.0915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.0588   -2.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1771   -0.3675    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.6481   -3.7510    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   31.2310   -3.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6645   -1.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4424   -2.0438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0090   -3.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1812   -4.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6146   -2.8426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  4  5  1  0
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  8  9  1  0
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 13 14  1  0
 11 15  2  0
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 17 18  2  0
 17 19  1  0
 19 20  1  0
 10 21  1  6
 13 22  1  6
 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:

   

   ALA2206671

   (1S,5S)-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