(S)-((2S,4S,8S)-8-ethynylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methanamine

ID: ALA5203857

PubChem CID: 168293633

Max Phase: Preclinical

Molecular Formula: C20H23N3O

Molecular Weight: 321.42

Names and Identifiers

Canonical SMILES:  C#C[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](N)c1ccnc2ccc(OC)cc12

Standard InChI:  InChI=1S/C20H23N3O/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/h1,4-6,8,11,13-14,19-20H,7,9-10,12,21H2,2H3/t13-,14-,19-,20-/m0/s1

Standard InChI Key:  WFMMBXNNDRUEEF-FEBSWUBLSA-N

Molfile:  

 
     RDKit          2D

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    2.0560   -0.0586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2596   -0.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6020   -0.6586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6096   -1.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0480   -1.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0443   -2.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7135   -2.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3713   -2.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3636   -1.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7135   -1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0292   -1.4281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6869   -1.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6135   -2.9438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2714   -2.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2714   -1.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0557   -0.2779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2596    0.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0215    0.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6331    0.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6869   -0.4510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3521    1.0185    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1600    1.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3062    0.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1368    2.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -1.0048    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1138    2.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  6  5  1  0
  7  6  2  0
  7  8  1  0
  8  9  2  0
 10  5  2  0
  9 10  1  0
 11  9  1  0
 12 11  1  0
 13  6  1  0
 13 14  2  0
 14 15  1  0
 15  4  2  0
  3 16  1  6
 17  2  1  0
 18 17  1  0
 18 19  1  0
 20  1  1  0
 19 20  1  0
 18 21  1  6
 22 18  1  0
 23  1  1  0
 22 23  1  0
 22 24  1  1
  2 25  1  1
 24 26  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA5203857

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 321.42

Molecular Weight (Monoisotopic): 321.1841

AlogP: 2.59

#Rotatable Bonds: 3

Polar Surface Area: 51.38

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.94

CX LogP: 1.90

CX LogD: 0.35

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.88

Np Likeness Score: 0.12

References

1. Pósa SP, Dargó G, Nagy S, Kisszékelyi P, Garádi Z, Hámori L, Szakács G, Kupai J, Tóth S..  (2022)  Cytotoxicity of cinchona alkaloid organocatalysts against MES-SA and MES-SA/Dx5 multidrug-resistant uterine sarcoma cell lines.,  67  [PMID:35640378] [10.1016/j.bmc.2022.116855]

Source

Source(1):

• Scientific Literature