(+/-)-N-((6,6-diphenyl-1,4-dioxan-2-yl)methyl)-2-(2-nitrophenoxy)ethanamine

ID: ALA4067083

PubChem CID: 137631359

Max Phase: Preclinical

Molecular Formula: C25H26N2O5

Molecular Weight: 434.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1ccccc1OCCNCC1COCC(c2ccccc2)(c2ccccc2)O1

Standard InChI:  InChI=1S/C25H26N2O5/c28-27(29)23-13-7-8-14-24(23)31-16-15-26-17-22-18-30-19-25(32-22,20-9-3-1-4-10-20)21-11-5-2-6-12-21/h1-14,22,26H,15-19H2

Standard InChI Key:  VFNSXXVAZKMPQN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   27.8645  -20.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0449  -19.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1453  -19.7768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5475  -18.9852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5463  -19.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2341  -20.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9233  -19.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9206  -18.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2323  -18.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8587  -20.1775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1716  -19.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4839  -20.1764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7968  -19.7790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.1091  -20.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4221  -19.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4225  -18.9865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7394  -18.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0494  -18.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7344  -20.1785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0712  -20.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8906  -21.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5020  -22.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2967  -21.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4736  -21.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6993  -18.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8005  -18.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3514  -19.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8077  -20.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7049  -20.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8593  -18.5887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1720  -18.9857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8591  -17.7949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 15 14  1  0
 15 16  1  0
 15 19  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
  2 19  1  0
  1 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24  1  1  0
  3 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29  3  1  0
 30 31  2  0
 30 32  1  0
  4 30  1  0
M  CHG  2  30   1  32  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4067083

   ---

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: 434.49

Molecular Weight (Monoisotopic): 434.1842

AlogP: 3.92

#Rotatable Bonds: 9

Polar Surface Area: 82.86

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.81

CX LogP: 4.48

CX LogD: 3.06

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.31

Np Likeness Score: -0.35

References

1. Del Bello F, Bonifazi A, Giannella M, Giorgioni G, Piergentili A, Petrelli R, Cifani C, Micioni Di Bonaventura MV, Keck TM, Mazzolari A, Vistoli G, Cilia A, Poggesi E, Matucci R, Quaglia W..  (2017)  The replacement of the 2-methoxy substituent of N-((6,6-diphenyl-1,4-dioxan-2-yl)methyl)-2-(2-methoxyphenoxy)ethan-1-amine improves the selectivity for 5-HT1A receptor over α1-adrenoceptor and D2-like receptor subtypes.,  125  [PMID:27662034] [10.1016/j.ejmech.2016.09.026]

Source

Source(1):

• Scientific Literature