3-(2-Phenanthrenyl)octahydro-1,4-pyrido[2,1-c]oxazin-3-ol hydrobromide

ID: ALA3623842

PubChem CID: 122192823

Max Phase: Preclinical

Molecular Formula: C22H24BrNO2

Molecular Weight: 333.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Br.OC1(c2ccc3c(ccc4ccccc43)c2)CN2CCCCC2CO1

Standard InChI:  InChI=1S/C22H23NO2.BrH/c24-22(15-23-12-4-3-6-19(23)14-25-22)18-10-11-21-17(13-18)9-8-16-5-1-2-7-20(16)21;/h1-2,5,7-11,13,19,24H,3-4,6,12,14-15H2;1H

Standard InChI Key:  WJFKJJKYLNFSEY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    5.5631   -2.2793    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -6.0106   -3.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6829   -5.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3646   -7.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332   -2.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9867   -4.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3936   -4.5183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4082   -3.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7200   -2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7639   -1.7207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277   -1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0753   -6.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6684   -6.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0898   -5.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332    0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205   -1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558   -2.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7503   -1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558    0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7503    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0631    0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0631    2.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7503    2.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558    2.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  3  1  0
  4 13  1  0
 16 11  2  0
 12  9  1  0
  7  8  1  0
  3 14  1  0
  8  9  1  0
 14  4  1  0
  7 15  1  0
 12  5  2  0
  9  2  1  0
  5 18  1  0
 17 16  1  0
  6  2  1  0
 11 12  1  0
 13 15  1  0
  9 10  1  0
  6  3  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 22  2  0
 21 17  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
M  END

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: 333.43

Molecular Weight (Monoisotopic): 333.1729

AlogP: 4.02

#Rotatable Bonds: 1

Polar Surface Area: 32.70

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.93

CX Basic pKa: 6.97

CX LogP: 4.46

CX LogD: 4.32

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.68

Np Likeness Score: 0.32

References

1. Ladopoulou EM, Matralis AN, Nikitakis A, Kourounakis AP..  (2015)  Antihyperlipidemic morpholine derivatives with antioxidant activity: An investigation of the aromatic substitution.,  23  (21): [PMID:26433631] [10.1016/j.bmc.2015.09.034]

Source

Source(1):

• Scientific Literature