4-[6-Amino-5-(2-methoxypyrimidin-5-yl)pyridin-3-yl]benzoic acid

ID: ALA4743812

PubChem CID: 162647383

Max Phase: Preclinical

Molecular Formula: C17H14N4O3

Molecular Weight: 322.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ncc(-c2cc(-c3ccc(C(=O)O)cc3)cnc2N)cn1

Standard InChI:  InChI=1S/C17H14N4O3/c1-24-17-20-8-13(9-21-17)14-6-12(7-19-15(14)18)10-2-4-11(5-3-10)16(22)23/h2-9H,1H3,(H2,18,19)(H,22,23)

Standard InChI Key:  NIOQYHHHCUJZIQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   17.7952   -9.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7940  -10.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5021  -10.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2118  -10.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2089   -9.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5003   -9.3231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9166  -10.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9165  -11.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6241  -12.1835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3321  -11.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3282  -10.9523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6201  -10.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9151   -9.3171    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0879  -10.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3802  -10.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6727  -10.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6716  -11.7744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3840  -12.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0886  -11.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9611  -12.1849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2531  -11.7767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9615  -13.0021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0410  -12.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7475  -11.7696    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
  4  7  1  0
  5 13  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  2 14  1  0
 20 21  1  0
 20 22  2  0
 17 20  1  0
 10 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4743812

   ---

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: 322.32

Molecular Weight (Monoisotopic): 322.1066

AlogP: 2.49

#Rotatable Bonds: 4

Polar Surface Area: 111.22

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.02

CX Basic pKa: 6.86

CX LogP: 0.38

CX LogD: -0.24

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.76

Np Likeness Score: -0.37

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