(R)-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: ALA2206676

PubChem CID: 71450624

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-KBUPBQIOSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    3.1929  -18.2313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4981  -17.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3073  -17.3586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5569  -16.5828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3213  -16.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7656  -18.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0268  -16.6985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5815  -18.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1403  -17.5067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3530  -18.7432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1876  -17.1753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9194  -17.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0957  -18.5509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5223  -17.2013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3012  -17.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9028  -16.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7306  -16.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9511  -15.8564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3438  -16.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4196  -15.4773    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8906  -18.8608    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3838  -18.3460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0786  -19.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6968  -18.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9943  -16.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2995  -16.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7957  -15.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1086  -15.9572    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  1
 25 26  1  0
 26 27  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2206676

   methyl (2R)-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]

Source

Source(1):

• Scientific Literature