N-(4-(1H-imidazol-1-yl)phenyl)-1-(benzo[d][1,3]dioxol-5-ylmethyl)piperidin-3-amine

ID: ALA233031

PubChem CID: 22260066

Max Phase: Preclinical

Molecular Formula: C22H24N4O2

Molecular Weight: 376.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1cn(-c2ccc(NC3CCCN(Cc4ccc5c(c4)OCO5)C3)cc2)cn1

Standard InChI:  InChI=1S/C22H24N4O2/c1-2-19(24-18-4-6-20(7-5-18)26-11-9-23-15-26)14-25(10-1)13-17-3-8-21-22(12-17)28-16-27-21/h3-9,11-12,15,19,24H,1-2,10,13-14,16H2

Standard InChI Key:  KYDUFQIZMRXXFB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
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   -4.4991  -10.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5020   -9.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2173   -8.9644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9332  -10.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9365   -9.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7202   -9.1286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2050   -9.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7172  -10.4623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7890   -8.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7921   -8.1333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5042   -6.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5042   -7.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0801   -7.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0801   -6.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7921   -6.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645   -6.4896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6512   -6.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6552   -7.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2261   -7.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2263   -6.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9394   -6.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4877   -8.1479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5749   -8.9681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3816   -9.1409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7953   -8.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2441   -7.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
 12 16  1  0
 13 11  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
  6  7  1  0
 15 17  1  0
  7  8  1  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
  9  5  1  0
 19 20  1  0
  4  6  1  0
 20 21  2  0
  3 10  1  0
 21 22  1  0
  5  6  2  0
 22 23  2  0
 23 18  1  0
 10 11  1  0
 21 24  1  0
 24 25  1  0
 12 13  1  0
  1  2  2  0
  5  1  1  0
  2  3  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA233031

   N-(4-(1H-imidazol-1-yl)phenyl)-1-(benzo[d][1,3]dioxol-5-ylmethyl)piperidin-3-amine

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: 376.46

Molecular Weight (Monoisotopic): 376.1899

AlogP: 3.68

#Rotatable Bonds: 5

Polar Surface Area: 51.55

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.21

CX LogP: 3.04

CX LogD: 2.16

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.74

Np Likeness Score: -1.74

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