5-{5-Methyl-2-[(pyridin-4-ylmethyl)-carbamoyl]-pyridin-4-yl}-1Hindole-2-carboxylic Acid Ethyl Ester

ID: ALA1939878

Chembl Id: CHEMBL1939878

PubChem CID: 45377565

Max Phase: Preclinical

Molecular Formula: C24H22N4O3

Molecular Weight: 414.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc2cc(-c3cc(C(=O)NCc4ccncc4)ncc3C)ccc2[nH]1

Standard InChI:  InChI=1S/C24H22N4O3/c1-3-31-24(30)22-11-18-10-17(4-5-20(18)28-22)19-12-21(26-13-15(19)2)23(29)27-14-16-6-8-25-9-7-16/h4-13,28H,3,14H2,1-2H3,(H,27,29)

Standard InChI Key:  DMKUTALHEIQGEX-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1939878

   ethyl 5-[5-methyl-2-(pyridin-4-ylmethylcarbamoyl)pyridin-4-yl]-1H-indole-2-carboxylate

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: 414.47

Molecular Weight (Monoisotopic): 414.1692

AlogP: 4.04

#Rotatable Bonds: 6

Polar Surface Area: 96.97

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.17

CX Basic pKa: 5.02

CX LogP: 3.26

CX LogD: 3.26

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.46

Np Likeness Score: -1.07

References

1. Taylor SJ, Abeywardane A, Liang S, Muegge I, Padyana AK, Xiong Z, Hill-Drzewi M, Farmer B, Li X, Collins B, Li JX, Heim-Riether A, Proudfoot J, Zhang Q, Goldberg D, Zuvela-Jelaska L, Zaher H, Li J, Farrow NA..  (2011)  Fragment-based discovery of indole inhibitors of matrix metalloproteinase-13.,  54  (23): [PMID:22017539] [10.1021/jm201129m]

2.  (2014)  Heteroaryl substituted indole compounds useful as MMP-13 inhibitors, 

Source

Source(2):

• Scientific Literature
• BindingDB Database