(S)-Methyl 4-methyl-2-[(1S,5S,7S)-2-oxo-7-(piperidine-1-carbonyl)-6,8-dioxa-3-azabicyclo[3.2.1]octan-3-yl)]pentanoate

ID: ALA2206675

PubChem CID: 71457775

Max Phase: Preclinical

Molecular Formula: C18H28N2O6

Molecular Weight: 368.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](CC(C)C)N1C[C@H]2O[C@H](C(=O)N3CCCCC3)[C@H](O2)C1=O

Standard InChI:  InChI=1S/C18H28N2O6/c1-11(2)9-12(18(23)24-3)20-10-13-25-14(15(26-13)17(20)22)16(21)19-7-5-4-6-8-19/h11-15H,4-10H2,1-3H3/t12-,13-,14-,15-/m0/s1

Standard InChI Key:  MNTZQPYJSPFTGX-AJNGGQMLSA-N

Molfile:  

     RDKit          2D

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   27.6013  -10.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9066   -9.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7157   -9.1702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.9653   -8.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7298   -8.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1740   -9.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4352   -8.5101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9899   -9.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5487   -9.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7614  -10.5548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5960   -8.9868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3279   -9.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5042  -10.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9308   -9.0129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.7097   -9.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3112   -8.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1390   -7.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3595   -7.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7522   -8.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8280   -7.2889    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   30.2990  -10.6724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.7922  -10.1575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4870  -10.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1052  -10.6862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4027   -8.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7080   -7.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2041   -7.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5171   -7.7687    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
  3  6  1  0
  5  7  1  0
  6  8  1  0
  7  9  1  0
  8  9  1  0
  6 10  2  0
  5 11  1  0
 11  8  1  0
  9 12  1  6
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
  5 20  1  6
  8 21  1  6
  1 22  1  0
 22 23  1  0
  1 24  2  0
  2 25  1  6
 25 26  1  0
 26 27  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2206675

   methyl (2S)-4-methyl-2-[(1S,5S,7S)-2-oxo-7-(piperidine-1-carbonyl)-6,8-dioxa-3-azabicyclo[3.2.1]octan-3-yl]pentanoate

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: 368.43

Molecular Weight (Monoisotopic): 368.1947

AlogP: 0.54

#Rotatable Bonds: 5

Polar Surface Area: 85.38

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.04

CX Basic pKa: ┄

CX LogP: 1.02

CX LogD: 1.02

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.66

Np Likeness Score: -0.14

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