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

ID: ALA4554777

PubChem CID: 135357363

Max Phase: Preclinical

Molecular Formula: C26H23ClN4O2

Molecular Weight: 458.95

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(-c2ccc(C3CCNCC3)cc2)cc(-n2cc(-c3ccc(Cl)cc3)nn2)c1

Standard InChI:  InChI=1S/C26H23ClN4O2/c27-23-7-5-20(6-8-23)25-16-31(30-29-25)24-14-21(13-22(15-24)26(32)33)18-3-1-17(2-4-18)19-9-11-28-12-10-19/h1-8,13-16,19,28H,9-12H2,(H,32,33)

Standard InChI Key:  MWYDACTYSOSUPV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
    5.7739  -18.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5894  -18.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9963  -17.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5889  -17.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7704  -17.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3671  -17.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8097  -17.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2175  -18.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0339  -18.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4435  -17.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0307  -17.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2156  -17.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2590  -17.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6671  -18.6670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4807  -18.6681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8924  -17.9617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4842  -17.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6644  -17.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3591  -16.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7650  -15.8427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5419  -16.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3661  -19.3763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5534  -19.4620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3837  -20.2614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0915  -20.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6986  -20.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1756  -21.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5130  -21.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5983  -22.7719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3455  -23.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0084  -22.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9198  -21.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4323  -23.9174    0.0000 Cl  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
M  END

Alternative Forms

1. Parent:

   

   ALA4554777

   ---

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: 458.95

Molecular Weight (Monoisotopic): 458.1510

AlogP: 5.42

#Rotatable Bonds: 5

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: 3.25

CX LogD: 3.25

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.42

Np Likeness Score: -1.03

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