1-3-[3-(tert-butyl) phenyl]-5-N,N-dimethylaminomethyl-(1,2,4-triazol-4-yl)]-3-phenol

ID: ALA211226

PubChem CID: 11595485

Max Phase: Preclinical

Molecular Formula: C21H26N4O

Molecular Weight: 350.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)Cc1nnc(-c2cccc(C(C)(C)C)c2)n1-c1cccc(O)c1

Standard InChI:  InChI=1S/C21H26N4O/c1-21(2,3)16-9-6-8-15(12-16)20-23-22-19(14-24(4)5)25(20)17-10-7-11-18(26)13-17/h6-13,26H,14H2,1-5H3

Standard InChI Key:  XTUDDOLKBSGVEE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -1.4306   -0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4318   -1.4398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7169   -1.8527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0005   -1.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034   -0.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7187   -0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7207    0.6252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0547    1.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3120    1.8960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1371    1.8936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3895    1.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1165    0.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129    1.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5438    0.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5796   -0.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8784   -0.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1503   -0.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146   -1.8507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9107   -1.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6408   -1.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2130   -1.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9167   -2.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307    0.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3421    1.4135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1275    1.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1681    2.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
  7  8  1  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
  3  4  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 11 12  1  0
  4  5  1  0
  4 18  1  0
  2  3  1  0
 16 19  1  0
  8  9  2  0
 19 20  1  0
  9 10  1  0
 19 21  1  0
 10 11  2  0
 19 22  1  0
 11  7  1  0
  8 23  1  0
  6  7  1  0
 23 24  1  0
  5  6  2  0
 24 25  1  0
  6  1  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA211226

   3-(3-(3-tert-butylphenyl)-5-((dimethylamino)methyl)-4H-1,2,4-triazol-4-yl)phenol

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: 350.47

Molecular Weight (Monoisotopic): 350.2107

AlogP: 4.00

#Rotatable Bonds: 4

Polar Surface Area: 54.18

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.01

CX Basic pKa: 6.73

CX LogP: 4.06

CX LogD: 3.97

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.77

Np Likeness Score: -1.50

References

1. Zhang Q, Keenan SM, Peng Y, Nair AC, Yu SJ, Howells RD, Welsh WJ..  (2006)  Discovery of novel triazole-based opioid receptor antagonists.,  49  (14): [PMID:16821764] [10.1021/jm0601250]

2. Peng Y, Zhang Q, Arora S, Keenan SM, Kortagere S, Wannemacher KM, Howells RD, Welsh WJ..  (2009)  Novel delta opioid receptor agonists exhibit differential stimulation of signaling pathways.,  17  (17): [PMID:19646882] [10.1016/j.bmc.2009.07.007]

Source

Source(1):

• Scientific Literature