5-{2-Methyl-5-[(6-oxo-1,6-dihydro-pyridin-3-ylmethyl)-carbamoyl]-2H-pyrazol-3-yl}-1H-indole-2-carboxylic Acid Ethyl Ester

ID: ALA1939875

Chembl Id: CHEMBL1939875

PubChem CID: 45377703

Max Phase: Preclinical

Molecular Formula: C22H21N5O4

Molecular Weight: 419.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc2cc(-c3cc(C(=O)NCc4ccc(=O)[nH]c4)nn3C)ccc2[nH]1

Standard InChI:  InChI=1S/C22H21N5O4/c1-3-31-22(30)18-9-15-8-14(5-6-16(15)25-18)19-10-17(26-27(19)2)21(29)24-12-13-4-7-20(28)23-11-13/h4-11,25H,3,12H2,1-2H3,(H,23,28)(H,24,29)

Standard InChI Key:  REANBRVQFZEMPZ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1939875

   ethyl 5-[2-methyl-5-[(6-oxo-1H-pyridin-3-yl)methylcarbamoyl]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: 419.44

Molecular Weight (Monoisotopic): 419.1594

AlogP: 2.36

#Rotatable Bonds: 6

Polar Surface Area: 121.87

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.86

CX Basic pKa: 0.16

CX LogP: 1.31

CX LogD: 1.31

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.41

Np Likeness Score: -1.34

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