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

ID: ALA4476579

PubChem CID: 135357334

Max Phase: Preclinical

Molecular Formula: C26H23FN4O2

Molecular Weight: 442.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(-c2ccc(C3CCNCC3)cc2)cc(-n2cc(-c3cccc(F)c3)nn2)c1

Standard InChI:  InChI=1S/C26H23FN4O2/c27-23-3-1-2-20(13-23)25-16-31(30-29-25)24-14-21(12-22(15-24)26(32)33)18-6-4-17(5-7-18)19-8-10-28-11-9-19/h1-7,12-16,19,28H,8-11H2,(H,32,33)

Standard InChI Key:  GFLWFROMYHSLMY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    5.0640  -19.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8795  -19.4377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2864  -18.7332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8790  -18.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0605  -18.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5076  -19.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3240  -19.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7336  -18.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3208  -18.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5057  -18.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5491  -18.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9572  -19.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7708  -19.4398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1825  -18.7335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7744  -18.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9546  -18.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6492  -17.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0551  -16.6145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8320  -17.3268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6562  -20.1481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8435  -20.2338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6738  -21.0331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3816  -21.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9887  -20.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4658  -22.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8031  -22.7317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8884  -23.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6356  -23.8766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2985  -23.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2099  -22.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2272  -24.0239    0.0000 F   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
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  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
 29 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476579

   ---

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: 442.49

Molecular Weight (Monoisotopic): 442.1805

AlogP: 4.91

#Rotatable Bonds: 5

Polar Surface Area: 80.04

Molecular Species: ZWITTERION

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.85

CX Basic pKa: 10.07

CX LogP: 2.79

CX LogD: 2.79

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.46

Np Likeness Score: -1.17

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