5-fluoro-2-((3-(pyrimidin-2-yl)pyridin-2-ylamino)methyl)phenol

ID: ALA3613794

Cas Number: 1575392-43-6

PubChem CID: 72376515

Max Phase: Preclinical

Molecular Formula: C16H13FN4O

Molecular Weight: 296.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1cc(F)ccc1CNc1ncccc1-c1ncccn1

Standard InChI:  InChI=1S/C16H13FN4O/c17-12-5-4-11(14(22)9-12)10-21-16-13(3-1-6-18-16)15-19-7-2-8-20-15/h1-9,22H,10H2,(H,18,21)

Standard InChI Key:  YTVDOVJPKJLMHL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2004    2.9933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4995    3.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7985    2.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7985    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4994    0.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4994   -0.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2015   -1.5097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2039   -3.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5041   -3.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8020   -3.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7996   -1.5056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383   -1.3500    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
  3  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 15 16  1  0
  1 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3613794

   5-Fluoro-2-({[3-(Pyrimidin-2-Yl)pyridin-2-Yl]amino}methyl)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: 296.31

Molecular Weight (Monoisotopic): 296.1073

AlogP: 3.00

#Rotatable Bonds: 4

Polar Surface Area: 70.93

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.27

CX Basic pKa: 5.48

CX LogP: 2.94

CX LogD: 2.88

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.77

Np Likeness Score: -1.10

References

1. Pollock J, Borkin D, Lund G, Purohit T, Dyguda-Kazimierowicz E, Grembecka J, Cierpicki T..  (2015)  Rational Design of Orthogonal Multipolar Interactions with Fluorine in Protein-Ligand Complexes.,  58  (18): [PMID:26288158] [10.1021/acs.jmedchem.5b00975]

Source

Source(1):

• Scientific Literature