2-(2-Phenanthrenyl)-4-methyloctahydro-1,4-benzoxazin-2-ol hydrobromide

ID: ALA3623843

PubChem CID: 122192825

Max Phase: Preclinical

Molecular Formula: C23H26BrNO2

Molecular Weight: 347.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Br.CN1CC(O)(c2ccc3c(ccc4ccccc43)c2)OC2CCCCC21

Standard InChI:  InChI=1S/C23H25NO2.BrH/c1-24-15-23(25,26-22-9-5-4-8-21(22)24)18-12-13-20-17(14-18)11-10-16-6-2-3-7-19(16)20;/h2-3,6-7,10-14,21-22,25H,4-5,8-9,15H2,1H3;1H

Standard InChI Key:  QTQGWTUZENVENF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    5.5631   -2.2908    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -5.7643   -1.7209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7204   -2.3127    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
   -3.4149   -4.5217    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4175   -3.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0196   -3.0443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3729   -5.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7057   -5.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0081   -4.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2989   -5.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2873   -6.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9849   -7.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6941   -6.7770    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
   -2.1332    0.6928    0.0000 C   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
   -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
  3  2  1  0
  4  3  1  0
 10  7  1  0
  9  5  1  0
  5  6  1  0
  6  3  1  0
  3  7  1  0
  5  8  1  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  4 15  2  0
 15 19  1  0
 18 16  1  0
 16 17  2  0
 17  4  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 23  2  0
 22 18  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  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: 347.46

Molecular Weight (Monoisotopic): 347.1885

AlogP: 4.41

#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: 7.40

CX LogP: 4.96

CX LogD: 4.66

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.66

Np Likeness Score: 0.57

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