(S)-4-[((1S,2S,4S,5R)-5-Ethyl-1-azabicyclo[2.2.2]octan-2-yl)-fluoromethyl]-6-methoxyquinoline

ID: ALA4537454

PubChem CID: 44234648

Max Phase: Preclinical

Molecular Formula: C20H25FN2O

Molecular Weight: 328.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC[C@H]1C[N@]2CC[C@H]1C[C@@H]2[C@H](F)c1ccnc2ccc(OC)cc12

Standard InChI:  InChI=1S/C20H25FN2O/c1-3-13-12-23-9-7-14(13)10-19(23)20(21)16-6-8-22-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20H,3,7,9-10,12H2,1-2H3/t13-,14-,19+,20+/m0/s1

Standard InChI Key:  AIGRCCSKIYGXPT-AFHBHXEDSA-N

Molfile:  

 
     RDKit          2D

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    8.3617   -4.7881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4995   -5.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7946   -6.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7864   -5.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0816   -6.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4995   -4.2742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6312   -3.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3244   -4.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4737   -3.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0457   -5.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0858   -7.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7989   -7.9140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3603   -6.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4488   -2.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9835   -4.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3603   -7.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0733   -5.0245    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6555   -6.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5118   -7.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6472   -7.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5118   -6.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9341   -6.2723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7067   -5.8122    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5989   -3.6192    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1470   -1.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2296   -6.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4  2  1  0
  5  3  1  0
  6  2  1  0
  8 15  1  0
  9  7  1  0
 10  1  1  0
 11  5  1  0
 12 19  2  0
 13  5  2  0
  9 14  1  1
 15 10  1  0
 16 11  2  0
  4 17  1  1
 18 13  1  0
 19 21  1  0
 20 18  2  0
 21  3  2  0
 22 18  1  0
  2 23  1  6
  8 24  1  6
  9  8  1  0
  8  6  1  0
 12 11  1  0
 16 20  1  0
 14 25  1  0
 22 26  1  0
  1  7  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4537454

   4-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-fluoromethyl]-6-methoxyquinoline

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 328.43

Molecular Weight (Monoisotopic): 328.1951

AlogP: 4.37

#Rotatable Bonds: 4

Polar Surface Area: 25.36

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.06

CX LogP: 3.71

CX LogD: 2.96

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.83

Np Likeness Score: 0.10

References

1. Wang X, Zeng Y, Sheng L, Larson P, Liu X, Zou X, Wang S, Guo K, Ma C, Zhang G, Cui H, Ferguson DM, Li Y, Zhang J, Aldrich CC..  (2019)  A Cinchona Alkaloid Antibiotic That Appears To Target ATP Synthase in Streptococcus pneumoniae.,  62  (5): [PMID:30779564] [10.1021/acs.jmedchem.8b01353]

Source

Source(1):

• Scientific Literature