5-{2-Methyl-5-[(pyridin-4-ylmethyl)-carbamoyl]-2H-pyrazol-3-yl}-1H-indole-2-carboxylic Acid Ethyl Ester

ID: ALA1939874

Chembl Id: CHEMBL1939874

PubChem CID: 45377564

Max Phase: Preclinical

Molecular Formula: C22H21N5O3

Molecular Weight: 403.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc2cc(-c3cc(C(=O)NCc4ccncc4)nn3C)ccc2[nH]1

Standard InChI:  InChI=1S/C22H21N5O3/c1-3-30-22(29)19-11-16-10-15(4-5-17(16)25-19)20-12-18(26-27(20)2)21(28)24-13-14-6-8-23-9-7-14/h4-12,25H,3,13H2,1-2H3,(H,24,28)

Standard InChI Key:  XYAPTVNWZXNGOT-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1939874

   ethyl 5-[2-methyl-5-(pyridin-4-ylmethylcarbamoyl)pyrazol-3-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: 403.44

Molecular Weight (Monoisotopic): 403.1644

AlogP: 3.07

#Rotatable Bonds: 6

Polar Surface Area: 101.90

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.12

CX Basic pKa: 5.02

CX LogP: 2.31

CX LogD: 2.31

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.48

Np Likeness Score: -1.55

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