ethyl 2-((2-(4-(1H-imidazol-1-yl)phenoxy)ethyl)(benzo[d][1,3]dioxol-5-ylmethyl)amino)acetate

ID: ALA396273

PubChem CID: 10387584

Max Phase: Preclinical

Molecular Formula: C23H25N3O5

Molecular Weight: 423.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)CN(CCOc1ccc(-n2ccnc2)cc1)Cc1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C23H25N3O5/c1-2-28-23(27)15-25(14-18-3-8-21-22(13-18)31-17-30-21)11-12-29-20-6-4-19(5-7-20)26-10-9-24-16-26/h3-10,13,16H,2,11-12,14-15,17H2,1H3

Standard InChI Key:  QKBJVYOXPPHUJY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    1.1076   -5.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1047   -6.3122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3926   -6.7225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3210   -6.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0373   -6.7202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7507   -6.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7534   -5.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4607   -5.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1808   -5.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1833   -6.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8928   -5.0731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0121   -4.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8232   -4.1182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2040   -4.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6378   -5.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8182   -6.7236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1049   -7.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1016   -8.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5290   -7.9594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5269   -8.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8187   -9.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9936  -10.0064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8093  -10.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1420   -9.3457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3940   -4.2408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3243   -5.4717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1084   -3.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1122   -3.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 13  1  0
  4  5  1  0
  3 18  1  0
  2  3  1  0
 18 19  1  0
  5  6  1  0
 19 20  2  0
  7 12  1  0
 20 21  1  0
 21 24  2  0
  8  9  1  0
 23 22  2  0
 22 19  1  0
 23 24  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  1  2  1  0
 10 13  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 23  1  0
 13 14  1  0
  1 28  1  0
  6  7  1  0
  1 29  2  0
  7  8  2  0
 28 30  1  0
  3  4  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA396273

   Ethyl 2-[1,3-benzodioxol-5-ylmethyl-[2-(4-imidazol-1-ylphenoxy)ethyl]amino]acetate

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: 423.47

Molecular Weight (Monoisotopic): 423.1794

AlogP: 3.05

#Rotatable Bonds: 10

Polar Surface Area: 75.05

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.27

CX LogP: 2.93

CX LogD: 2.90

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.46

Np Likeness Score: -1.69

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