1-hydroxy-6-(1-(3-methoxypropyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-4-phenylpyridin-2(1H)-one

ID: ALA2203964

Chembl Id: CHEMBL2203964

PubChem CID: 70679296

Max Phase: Preclinical

Molecular Formula: C22H21N3O3

Molecular Weight: 375.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCCn1ccc2cc(-c3cc(-c4ccccc4)cc(=O)n3O)cnc21

Standard InChI:  InChI=1S/C22H21N3O3/c1-28-11-5-9-24-10-8-17-12-19(15-23-22(17)24)20-13-18(14-21(26)25(20)27)16-6-3-2-4-7-16/h2-4,6-8,10,12-15,27H,5,9,11H2,1H3

Standard InChI Key:  MIWLVFZOCHMICD-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2203964

   1-Hydroxy-6-[1-(3-Methoxypropyl)-1h-Pyrrolo[2,3-B]pyridin-5-Yl]-4-Phenylpyridin-2(1h)-One

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: 375.43

Molecular Weight (Monoisotopic): 375.1583

AlogP: 3.81

#Rotatable Bonds: 6

Polar Surface Area: 69.28

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.60

CX Basic pKa: 3.13

CX LogP: 2.31

CX LogD: 1.46

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.41

Np Likeness Score: -0.69

References

1. Chiba T, Ohwada J, Sakamoto H, Kobayashi T, Fukami TA, Irie M, Miura T, Ohara K, Koyano H..  (2012)  Design and evaluation of azaindole-substituted N-hydroxypyridones as glyoxalase I inhibitors.,  22  (24): [PMID:23122816] [10.1016/j.bmcl.2012.10.045]

2. Perez C, Barkley-Levenson AM, Dick BL, Glatt PF, Martinez Y, Siegel D, Momper JD, Palmer AA, Cohen SM..  (2019)  Metal-Binding Pharmacophore Library Yields the Discovery of a Glyoxalase 1 Inhibitor.,  62  (3): [PMID:30628789] [10.1021/acs.jmedchem.8b01868]

Source

Source(1):

• Scientific Literature