1-[(3-naphthalen-2-yl)-5-N,N-dimethylamino-(1,2,4-triazol-4-yl)]-3-phenol

ID: ALA377643

PubChem CID: 11558993

Max Phase: Preclinical

Molecular Formula: C20H18N4O

Molecular Weight: 330.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1nnc(-c2ccc3ccccc3c2)n1-c1cccc(O)c1

Standard InChI:  InChI=1S/C20H18N4O/c1-23(2)20-22-21-19(24(20)17-8-5-9-18(25)13-17)16-11-10-14-6-3-4-7-15(14)12-16/h3-13,25H,1-2H3

Standard InChI Key:  RQQBVBFYGSVQNK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -0.3330  -24.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5951  -23.7976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9249  -23.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1883  -22.5181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0182  -22.5247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2689  -23.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2067  -23.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1918  -24.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4695  -24.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5035  -23.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5915  -24.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3054  -25.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3003  -25.8622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5820  -26.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8672  -25.8491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8758  -25.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1479  -26.2548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7807  -23.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7627  -24.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0391  -24.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3551  -23.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792  -23.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0524  -23.5769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6689  -23.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2207  -24.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
 12 13  1  0
 13 14  2  0
  7  8  2  0
 14 15  1  0
  2  3  1  0
 15 16  2  0
 16 11  1  0
  2 11  1  0
  8  9  1  0
 15 17  1  0
  9 19  2  0
  4  5  1  0
 18 19  1  0
 18 10  2  0
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 20  1  2  0
 10  7  1  0
  1 21  1  0
  3  7  1  0
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  5  6  2  0
  6 23  1  0
  6  2  1  0
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 11 12  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA377643

   3-[3-(Dimethylamino)-5-naphthalen-2-yl-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: 330.39

Molecular Weight (Monoisotopic): 330.1481

AlogP: 3.86

#Rotatable Bonds: 3

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: 9.99

CX Basic pKa: 2.27

CX LogP: 4.28

CX LogD: 4.28

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.62

Np Likeness Score: -0.97

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]

Source

Source(1):

• Scientific Literature