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

ID: ALA4561002

PubChem CID: 155558597

Max Phase: Preclinical

Molecular Formula: C22H30N2O2

Molecular Weight: 354.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCOc1ccc2nccc([C@@H](O)[C@@H]3C[C@@H]4CC[N@@]3C[C@@H]4CC)c2c1

Standard InChI:  InChI=1S/C22H30N2O2/c1-3-11-26-17-5-6-20-19(13-17)18(7-9-23-20)22(25)21-12-16-8-10-24(21)14-15(16)4-2/h5-7,9,13,15-16,21-22,25H,3-4,8,10-12,14H2,1-2H3/t15-,16-,21-,22+/m0/s1

Standard InChI Key:  OEZPJPMWUSVADU-WWLNLUSPSA-N

Molfile:  

 
     RDKit          2D

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    8.4380  -19.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7331  -20.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7247  -20.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0199  -21.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4380  -18.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5699  -18.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2630  -18.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4123  -17.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9846  -19.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0240  -22.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7372  -22.5398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2984  -20.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3874  -16.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9225  -19.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2984  -22.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0115  -19.6498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5934  -21.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4505  -22.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5852  -22.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4505  -21.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8721  -20.8978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6453  -20.4377    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5375  -18.2441    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0857  -16.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1672  -21.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4502  -20.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7455  -21.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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 12 19  2  0
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  9 14  1  1
 15 10  1  0
 16 11  2  0
  4 17  1  1
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 20 18  2  0
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 22 18  1  0
  2 23  1  1
  8 24  1  6
  9  8  1  0
  8  6  1  0
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 26 27  1  0
 27 28  1  0
  1  7  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4561002

   ---

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: 354.49

Molecular Weight (Monoisotopic): 354.2307

AlogP: 4.18

#Rotatable Bonds: 6

Polar Surface Area: 45.59

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.89

CX Basic pKa: 9.18

CX LogP: 3.70

CX LogD: 1.92

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.85

Np Likeness Score: 0.37

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