N-(1-(3-ethoxy-4-methoxybenzyl)piperidin-4-yl)-1H-benzo[d]imidazol-2-amine

ID: ALA1077724

PubChem CID: 46882668

Max Phase: Preclinical

Molecular Formula: C22H28N4O2

Molecular Weight: 380.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1cc(CN2CCC(Nc3nc4ccccc4[nH]3)CC2)ccc1OC

Standard InChI:  InChI=1S/C22H28N4O2/c1-3-28-21-14-16(8-9-20(21)27-2)15-26-12-10-17(11-13-26)23-22-24-18-6-4-5-7-19(18)25-22/h4-9,14,17H,3,10-13,15H2,1-2H3,(H2,23,24,25)

Standard InChI Key:  MSZPPOFTOFRJJR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -4.4186   -8.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4198   -9.3767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7078   -9.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7098   -8.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9926   -8.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9923   -9.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2066   -9.6245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7235   -8.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2078   -8.2935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8996   -8.9576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4869   -9.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8979  -10.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4891  -11.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3352  -11.0972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7488  -10.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3381   -9.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7449  -11.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5688  -11.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9757  -12.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7987  -12.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2138  -11.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7993  -11.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9777  -11.1019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2107  -10.3891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0345  -10.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4459   -9.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0377  -11.8179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4485  -12.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  5  4  2  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  6  7  1  0
 14 17  1  0
  7  8  2  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
  9  5  1  0
 19 20  1  0
  4  1  1  0
 20 21  2  0
  8 10  1  0
 21 22  1  0
  5  6  1  0
 22 23  2  0
 23 18  1  0
 10 11  1  0
 22 24  1  0
 11 12  1  0
 24 25  1  0
 25 26  1  0
  2  3  1  0
 21 27  1  0
  3  6  2  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1077724

   N-(1-(3-ethoxy-4-methoxybenzyl)piperidin-4-yl)-1H-benzo[d]imidazol-2-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: 380.49

Molecular Weight (Monoisotopic): 380.2212

AlogP: 4.05

#Rotatable Bonds: 7

Polar Surface Area: 62.41

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.41

CX Basic pKa: 7.86

CX LogP: 3.21

CX LogD: 2.57

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.65

Np Likeness Score: -1.28

References

1. Martin RE, Mohr P, Maerki HP, Guba W, Kuratli C, Gavelle O, Binggeli A, Bendels S, Alvarez-Sánchez R, Alker A, Polonchuk L, Christ AD..  (2009)  Benzoxazole piperidines as selective and potent somatostatin receptor subtype 5 antagonists.,  19  (21): [PMID:19786348] [10.1016/j.bmcl.2009.09.024]

Source

Source(1):

• Scientific Literature