5-(4-(4-Ethylphenyl)-1H-1,2,3-triazol-1-yl)-4'-(piperidin-4-yl)-[1,1'-biphenyl]-3-carboxylic Acid

ID: ALA4525685

PubChem CID: 135357030

Max Phase: Preclinical

Molecular Formula: C28H28N4O2

Molecular Weight: 452.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1ccc(-c2cn(-c3cc(C(=O)O)cc(-c4ccc(C5CCNCC5)cc4)c3)nn2)cc1

Standard InChI:  InChI=1S/C28H28N4O2/c1-2-19-3-5-23(6-4-19)27-18-32(31-30-27)26-16-24(15-25(17-26)28(33)34)21-9-7-20(8-10-21)22-11-13-29-14-12-22/h3-10,15-18,22,29H,2,11-14H2,1H3,(H,33,34)

Standard InChI Key:  NZRSCGSLTBWSMM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   33.1292  -10.8891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9446  -10.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3515  -10.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9442   -9.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1256   -9.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7224  -10.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   36.3892  -10.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7988  -10.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3860   -9.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5709   -9.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6142  -10.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0224  -10.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8360  -10.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2476  -10.1860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.8395   -9.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   32.7144   -8.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1203   -8.0670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8972   -8.7793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7213  -11.6006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9087  -11.6863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7389  -12.4857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.4468  -12.8941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0539  -12.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5309  -13.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8683  -14.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9535  -14.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7008  -15.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3636  -14.8439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2750  -14.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7875  -16.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1272  -16.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  3  7  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 10 13  1  0
  5 19  1  0
 19 20  1  0
 19 21  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 22  1  0
  1 22  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 25 27  1  0
 30 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4525685

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 452.56

Molecular Weight (Monoisotopic): 452.2212

AlogP: 5.33

#Rotatable Bonds: 6

Polar Surface Area: 80.04

Molecular Species: ZWITTERION

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.85

CX Basic pKa: 10.07

CX LogP: 3.61

CX LogD: 3.61

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.41

Np Likeness Score: -0.93

References

1. Junker A, Balasubramanian R, Ciancetta A, Uliassi E, Kiselev E, Martiriggiano C, Trujillo K, Mtchedlidze G, Birdwell L, Brown KA, Harden TK, Jacobson KA..  (2016)  Structure-Based Design of 3-(4-Aryl-1H-1,2,3-triazol-1-yl)-Biphenyl Derivatives as P2Y14 Receptor Antagonists.,  59  (13): [PMID:27331270] [10.1021/acs.jmedchem.6b00044]

Source

Source(1):

• Scientific Literature