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

ID: ALA2206672

PubChem CID: 71450623

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-/m1/s1

Standard InChI Key:  YLFMGINTBAGZCH-FRBBGCKASA-N

Molfile:  

     RDKit          2D

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   -0.4308  -11.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1269  -10.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299   -9.9933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3243   -9.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7638   -9.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3226   -9.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5353  -10.5053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3699   -8.9373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7046   -8.9634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4836   -9.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6019   -7.2394    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0729  -10.6229    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6558  -10.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0892   -8.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8672   -8.9156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4337  -10.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6060  -11.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0394   -9.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 13 22  1  1
 20 23  1  1
 20 24  1  0
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 26 27  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2206672

   (1R,5R)-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. 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