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

ID: ALA212375

PubChem CID: 11544824

Max Phase: Preclinical

Molecular Formula: C21H26N4O

Molecular Weight: 350.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)Cc1nnc(-c2ccc(C(C)(C)C)cc2)n1-c1cccc(O)c1

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

Standard InChI Key:  VARCIQVXDHUYNT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    6.4402   -0.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4391   -1.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1539   -1.9819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8703   -1.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8675   -0.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1521   -0.3289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1501    0.4961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8161    0.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5588    1.7669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7338    1.7644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4813    0.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7543    0.5985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0579    1.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3270    0.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2912   -0.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925   -0.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7206   -0.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5855   -1.9799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6015    0.7304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2129    1.2843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9983    1.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0390    2.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5603   -0.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8635   -0.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5261   -1.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -0.9500    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
  8 19  1  0
  8  9  2  0
 19 20  1  0
  9 10  1  0
 20 21  1  0
 10 11  2  0
 20 22  1  0
 11  7  1  0
 15 23  1  0
  6  7  1  0
 23 24  1  0
  5  6  2  0
 23 25  1  0
  6  1  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA212375

   3-(3-(4-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: 6.74

CX LogP: 4.06

CX LogD: 3.97

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.77

Np Likeness Score: -1.47

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