(4aR,5R,10bR)-5-Phenyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline

ID: ALA418127

PubChem CID: 6993322

Max Phase: Preclinical

Molecular Formula: C18H19NO

Molecular Weight: 265.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1ccc([C@@H]2Nc3ccccc3[C@@H]3OCCC[C@H]23)cc1

Standard InChI:  InChI=1S/C18H19NO/c1-2-7-13(8-3-1)17-15-10-6-12-20-18(15)14-9-4-5-11-16(14)19-17/h1-5,7-9,11,15,17-19H,6,10,12H2/t15-,17+,18+/m1/s1

Standard InChI Key:  NNBCJSIAXXSBNX-NJAFHUGGSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  1  0  0  0  0  0999 V2000
    5.3125    0.6833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292    0.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417    0.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417    1.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292    1.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3125    1.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4542    1.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292   -0.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4542    0.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292    2.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917    1.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1667    1.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3125   -0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1667    0.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3167    3.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917    2.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -1.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3125   -1.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292   -2.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417    2.3333    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -0.1500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  1  0
  6  1  1  0
  7  4  1  0
  2  8  1  6
  9  3  1  0
 10  5  2  0
 11  6  2  0
 12  7  1  0
 13  8  2  0
 14  8  1  0
 15  9  1  0
 16 17  2  0
 17 11  1  0
 18 14  2  0
 19 13  1  0
 20 18  1  0
  4 21  1  1
  3 22  1  1
  3  4  1  0
 10 16  1  0
 15 12  1  0
 19 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA418127

   (4aR,5R,10bR)-5-phenyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline

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: 265.36

Molecular Weight (Monoisotopic): 265.1467

AlogP: 4.32

#Rotatable Bonds: 1

Polar Surface Area: 21.26

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.71

CX LogP: 3.50

CX LogD: 3.50

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.83

Np Likeness Score: 0.04

References

1. Magesh CJ, Makesh SV, Perumal PT..  (2004)  Highly diastereoselective inverse electron demand (IED) Diels-Alder reaction mediated by chiral salen-AlCl complex: the first, target-oriented synthesis of pyranoquinolines as potential antibacterial agents.,  14  (9): [PMID:15080974] [10.1016/j.bmcl.2004.02.057]

Source

Source(1):

• Scientific Literature