N-methyl-quinine

ID: ALA2074787

PubChem CID: 10359785

Max Phase: Preclinical

Molecular Formula: C21H27N2O2+

Molecular Weight: 339.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H27N2O2/c1-4-14-13-23(2)10-8-15(14)11-20(23)21(24)17-7-9-22-19-6-5-16(25-3)12-18(17)19/h4-7,9,12,14-15,20-21,24H,1,8,10-11,13H2,2-3H3/q+1/t14-,15-,20-,21+,23?/m0/s1

Standard InChI Key:  SJTSZVLGFLZBFK-KBYCNLJVSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  1  0  0  0  0  0999 V2000
    4.9793    0.4416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9793    2.9166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6382   -1.5315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214    1.2666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2648   -0.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5504    0.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2648    0.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5504    1.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2873   -2.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359    1.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9127   -1.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1365   -2.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5197   -1.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8859   -2.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359    0.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2648    1.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7033   -2.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2648    2.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359    2.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214    0.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5504    2.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4541   -3.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2723   -3.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9793    3.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -0.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  1
  2 18  1  0
  2 24  1  0
  3  5  1  0
  3 13  1  0
  3 14  1  0
  4 10  1  0
  4 20  2  0
  5  7  1  0
  5 11  1  1
  6  7  1  0
  6  8  1  0
  6 15  2  0
  8 10  1  0
  8 16  2  0
  9 11  1  1
  9 12  1  0
  9 17  1  0
 10 19  2  0
 12 13  1  0
 12 22  1  6
 14 17  1  0
 15 20  1  0
 16 18  1  0
 18 21  2  0
 19 21  1  0
 22 23  2  0
  3 25  1  0
M  CHG  1   3   1
M  END

Alternative Forms

1. Parent:

   

   ALA2074787

   (R)-[(2S,4S,5R)-5-ethenyl-1-methyl-1-azoniabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol

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: 339.46

Molecular Weight (Monoisotopic): 339.2067

AlogP: 3.32

#Rotatable Bonds: 4

Polar Surface Area: 42.35

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.63

CX Basic pKa: 4.49

CX LogP: -1.65

CX LogD: -1.65

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.69

Np Likeness Score: 1.10

References

1. van Montfoort JE, Müller M, Groothuis GM, Meijer DK, Koepsell H, Meier PJ..  (2001)  Comparison of "type I" and "type II" organic cation transport by organic cation transporters and organic anion-transporting polypeptides.,  298  (1): [PMID:11408531]

2. van Montfoort JE, Hagenbuch B, Fattinger KE, Müller M, Groothuis GM, Meijer DK, Meier PJ..  (1999)  Polyspecific organic anion transporting polypeptides mediate hepatic uptake of amphipathic type II organic cations.,  291  (1): [PMID:10490898]

3. Pizzagalli F, Hagenbuch B, Stieger B, Klenk U, Folkers G, Meier PJ..  (2002)  Identification of a novel human organic anion transporting polypeptide as a high affinity thyroxine transporter.,  16  (1): [PMID:12351693] [10.1210/me.2001-0309]

4. Cattori V, van Montfoort JE, Stieger B, Landmann L, Meijer DK, Winterhalter KH, Meier PJ, Hagenbuch B..  (2001)  Localization of organic anion transporting polypeptide 4 (Oatp4) in rat liver and comparison of its substrate specificity with Oatp1, Oatp2 and Oatp3.,  443  (1): [PMID:11713643] [10.1007/s004240100697]

Source

Source(1):

• TP-search Transporter Database