(R)-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: ALA2206677

PubChem CID: 71461409

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+/m1/s1

Standard InChI Key:  MNTZQPYJSPFTGX-QPSCCSFWSA-N

Molfile:  

     RDKit          2D

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   12.8465  -17.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1517  -16.7303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9608  -16.6157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2105  -15.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9749  -15.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4192  -17.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6804  -15.9556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2351  -17.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7938  -16.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0066  -18.0003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8412  -16.4324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5730  -17.0101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7493  -17.8080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1759  -16.4584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9548  -16.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5564  -16.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3841  -15.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6046  -15.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9974  -15.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0732  -14.7344    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.5441  -18.1179    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0374  -17.6031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7321  -18.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3504  -18.1318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6479  -16.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9531  -15.3289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4492  -14.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7622  -15.2143    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  1
 25 26  1  0
 26 27  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2206677

   methyl (2R)-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