4-((6-((Carboxymethyl)carbamoyl)-5-hydroxypyridin-2-yl)-amino)benzoic Acid

ID: ALA5219135

PubChem CID: 168299658

Max Phase: Preclinical

Molecular Formula: C15H13N3O6

Molecular Weight: 331.28

Names and Identifiers

Canonical SMILES:  O=C(O)CNC(=O)c1nc(Nc2ccc(C(=O)O)cc2)ccc1O

Standard InChI:  InChI=1S/C15H13N3O6/c19-10-5-6-11(18-13(10)14(22)16-7-12(20)21)17-9-3-1-8(2-4-9)15(23)24/h1-6,19H,7H2,(H,16,22)(H,17,18)(H,20,21)(H,23,24)

Standard InChI Key:  MGSQMTWUEXIOHV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   18.6014  -20.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3091  -20.0088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0168  -20.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7245  -20.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4323  -20.4174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7245  -19.1916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8937  -20.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6014  -21.2346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8986  -19.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4857  -20.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1932  -20.4169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4831  -19.1907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1948  -18.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6083  -18.7854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7794  -20.4232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0703  -20.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0678  -19.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3595  -18.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6523  -19.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6578  -20.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3667  -20.4277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9426  -18.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9386  -17.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2369  -19.2109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  1  7  1  0
  1  8  2  0
  7  9  2  0
  9 13  1  0
 12 10  1  0
 10 11  2  0
 11  7  1  0
 12 13  2  0
  9 14  1  0
 10 15  1  0
 15 16  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
 19 22  1  0
 22 23  1  0
 22 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5219135

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 331.28

Molecular Weight (Monoisotopic): 331.0804

AlogP: 1.04

#Rotatable Bonds: 6

Polar Surface Area: 148.85

Molecular Species: ACID

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.31

CX Basic pKa: 3.40

CX LogP: 0.99

CX LogD: -4.49

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.53

Np Likeness Score: -0.74

References

1. Shishodia S, Demetriades M, Zhang D, Tam NY, Maheswaran P, Clunie-O'Connor C, Tumber A, Leung IKH, Ng YM, Leissing TM, El-Sagheer AH, Salah E, Brown T, Aik WS, McDonough MA, Schofield CJ..  (2021)  Structure-Based Design of Selective Fat Mass and Obesity Associated Protein (FTO) Inhibitors.,  64  (22.0): [PMID:34762429] [10.1021/acs.jmedchem.1c01204]

Source

Source(1):

• Scientific Literature