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

ID: ALA2206674

PubChem CID: 71461408

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-GBJTYRQASA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   18.6906  -10.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9959   -9.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8050   -9.2527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0546   -8.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8191   -8.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2633   -9.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5245   -8.5927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0792   -9.9984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6380   -9.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8508  -10.6374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6854   -9.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4172   -9.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5935  -10.4450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0201   -9.0954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7990   -9.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4006   -8.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2283   -7.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4488   -7.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8415   -8.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9173   -7.3714    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.3883  -10.7549    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.8815  -10.2401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5763  -10.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1945  -10.7688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4920   -8.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7973   -7.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2934   -7.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6064   -7.8513    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  1
 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  1
  8 21  1  1
  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:

   

   ALA2206674

   methyl (2S)-4-methyl-2-[(1R,5R,7R)-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]

2. Innocenti R, Lenci E, Menchi G, Pupi A, Trabocchi A..  (2017)  Design and synthesis of bicyclic acetals as Beta Secretase (BACE1) inhibitors.,  25  (19): [PMID:28359674] [10.1016/j.bmc.2017.03.030]

Source

Source(1):

• Scientific Literature