4-[6-Amino-5-(benzyloxy)pyridin-3-yl]benzoic acid

ID: ALA4756492

PubChem CID: 21111459

Max Phase: Preclinical

Molecular Formula: C19H16N2O3

Molecular Weight: 320.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncc(-c2ccc(C(=O)O)cc2)cc1OCc1ccccc1

Standard InChI:  InChI=1S/C19H16N2O3/c20-18-17(24-12-13-4-2-1-3-5-13)10-16(11-21-18)14-6-8-15(9-7-14)19(22)23/h1-11H,12H2,(H2,20,21)(H,22,23)

Standard InChI Key:  QPPKQHCOWKQUMH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   29.6362  -17.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6351  -18.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3431  -18.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0528  -18.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0499  -17.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3413  -17.0575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7576  -18.6922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7561  -17.0515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.9289  -18.6942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2213  -18.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5137  -18.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5126  -19.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2250  -19.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9296  -19.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8021  -19.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0941  -19.5111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8025  -20.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7578  -19.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4656  -19.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4622  -20.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1692  -21.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8778  -20.7317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8750  -19.9103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1674  -19.5056    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
  4  7  1  0
  5  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  2  9  1  0
 15 16  1  0
 15 17  2  0
 12 15  1  0
  7 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4756492

   4-(6-Amino-5-phenylmethoxypyridin-3-yl)benzoic acid

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: 320.35

Molecular Weight (Monoisotopic): 320.1161

AlogP: 3.61

#Rotatable Bonds: 5

Polar Surface Area: 85.44

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.01

CX Basic pKa: 7.04

CX LogP: 1.69

CX LogD: 1.19

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.75

Np Likeness Score: -0.35

References

1. Dow RL,Ammirati M,Bagley SW,Bhattacharya SK,Buckbinder L,Cortes C,El-Kattan AF,Ford K,Freeman GB,Guimarães CRW,Liu S,Niosi M,Skoura A,Tess D.  (2018)  2-Aminopyridine-Based Mitogen-Activated Protein Kinase Kinase Kinase Kinase 4 (MAP4K4) Inhibitors: Assessment of Mechanism-Based Safety.,  61  (7): [PMID:29570292] [10.1021/acs.jmedchem.8b00152]

Source

Source(1):

• Scientific Literature