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

ID: ALA2206673

PubChem CID: 71457774

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-GLDWBXLXSA-N

Molfile:  

     RDKit          2D

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    7.6563  -10.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1584  -11.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9700  -11.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2770  -10.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7729   -9.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0782   -9.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8873   -8.9597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   11.6068   -8.2996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1615   -9.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7203   -9.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9330  -10.3443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.6758  -10.1520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1023   -8.8024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8813   -9.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9996   -7.0784    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4706  -10.4619    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.0535   -9.8518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4869   -8.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2649   -8.7546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8314  -10.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0037  -10.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4371   -9.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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 17 18  2  0
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 19 20  1  0
 10 21  1  6
 13 22  1  6
 20 23  1  1
 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:

   

   ALA2206673

   (1S,5S)-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