3-(4-(1H-imidazol-1-yl)phenoxy)-1-(benzo[d][1,3]dioxol-5-ylmethyl)azepane

ID: ALA388880

PubChem CID: 10475555

Max Phase: Preclinical

Molecular Formula: C23H25N3O3

Molecular Weight: 391.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1cn(-c2ccc(OC3CCCCN(Cc4ccc5c(c4)OCO5)C3)cc2)cn1

Standard InChI:  InChI=1S/C23H25N3O3/c1-2-11-25(14-18-4-9-22-23(13-18)28-17-27-22)15-21(3-1)29-20-7-5-19(6-8-20)26-12-10-24-16-26/h4-10,12-13,16,21H,1-3,11,14-15,17H2

Standard InChI Key:  HGPUMTWTRGEZDO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   12.1400  -11.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5593  -10.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1472   -9.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3231   -9.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3145  -10.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9050  -10.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0981  -10.4473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0088  -11.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7606  -11.6049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5626   -8.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1530   -8.1381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0108   -6.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7554   -6.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4968   -6.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8181   -7.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6751   -7.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3269   -8.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1459   -6.1924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9114   -6.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0263   -7.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7910   -7.6257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4411   -7.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3214   -6.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5567   -5.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2070   -7.4229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4106   -8.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2338   -8.2740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5403   -7.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9066   -6.9799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 15  1  0
  3  4  2  0
 14 16  1  0
  6  7  1  0
 15 17  1  0
 16 11  1  0
 17 11  1  0
  7  8  1  0
 14 18  1  0
  8  9  1  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
  4  6  1  0
 20 21  1  0
  3 10  1  0
 21 22  2  0
  5  6  2  0
 22 23  1  0
 10 11  1  0
 23 24  2  0
 24 19  1  0
  1  2  2  0
 22 25  1  0
 25 26  1  0
  5  1  1  0
 12 13  1  0
  2  3  1  0
 13 14  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA388880

   1-(1,3-Benzodioxol-5-ylmethyl)-3-(4-imidazol-1-ylphenoxy)azepane

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: 391.47

Molecular Weight (Monoisotopic): 391.1896

AlogP: 4.03

#Rotatable Bonds: 5

Polar Surface Area: 48.75

Molecular Species: BASE

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.52

CX LogP: 3.86

CX LogD: 2.69

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.66

Np Likeness Score: -1.30

References

1. Wei RG, Adler M, Davey D, Ho E, Mohan R, Polokoff M, Tseng JL, Whitlow M, Xu W, Yuan S, Phillips G..  (2007)  1-(1,3-Benzodioxol-5-ylmethyl)-3-[4-(1H-imidazol-1-yl)phenoxy]-piperidine analogs as potent and selective inhibitors of nitric oxide formation.,  17  (9): [PMID:17368901] [10.1016/j.bmcl.2007.02.053]

Source

Source(1):

• Scientific Literature