N-(1H-indazol-5-yl)-2-methyl-4-(naphthalen-2-yl)-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxamide

ID: ALA441702

Chembl Id: CHEMBL441702

Cas Number: 864082-23-5

PubChem CID: 11269477

Max Phase: Preclinical

Molecular Formula: C24H20N4O2

Molecular Weight: 396.45

Molecule Type: Small molecule

Names and Identifiers

Synonyms: GSK270822A | GSK270822A|Rho-Kinase-IN-3|864082-23-5|N-(1H-indazol-5-yl)-2-methyl-4-(naphthalen-2-yl)-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxamide|N-(1H-Indazol-5-yl)-2-methyl-4-(2-naphthyl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide|N-(1H-indazol-5-yl)-6-methyl-4-naphthalen-2-yl-2-oxo-3,4-dihydro-1H-pyridine-5-carboxamide|CHEMBL441702|SCHEMBL3860469|BDBM14052|dihydropyridone indazole amide 12|ODLNBFNBEPOFNC-UHFFFAOYSA-N|HMS3303K01|HMS3305C12|NSC756163|AKOS040748470|NSC-756163|NCGC00241899-Show More⌵

Canonical SMILES:  CC1=C(C(=O)Nc2ccc3[nH]ncc3c2)C(c2ccc3ccccc3c2)CC(=O)N1

Standard InChI:  InChI=1S/C24H20N4O2/c1-14-23(24(30)27-19-8-9-21-18(11-19)13-25-28-21)20(12-22(29)26-14)17-7-6-15-4-2-3-5-16(15)10-17/h2-11,13,20H,12H2,1H3,(H,25,28)(H,26,29)(H,27,30)

Standard InChI Key:  ODLNBFNBEPOFNC-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA441702

   GSK-270822A

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: 396.45

Molecular Weight (Monoisotopic): 396.1586

AlogP: 4.23

#Rotatable Bonds: 3

Polar Surface Area: 86.88

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.11

CX Basic pKa: 1.72

CX LogP: 2.55

CX LogD: 2.55

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.48

Np Likeness Score: -1.22

References

1. Goodman KB, Cui H, Dowdell SE, Gaitanopoulos DE, Ivy RL, Sehon CA, Stavenger RA, Wang GZ, Viet AQ, Xu W, Ye G, Semus SF, Evans C, Fries HE, Jolivette LJ, Kirkpatrick RB, Dul E, Khandekar SS, Yi T, Jung DK, Wright LL, Smith GK, Behm DJ, Bentley R, Doe CP, Hu E, Lee D..  (2007)  Development of dihydropyridone indazole amides as selective Rho-kinase inhibitors.,  50  (1): [PMID:17201405] [10.1021/jm0609014]

2. Compounds: GSK PKIS; Assays: Nanosyn kinase panel,  [10.6019/CHEMBL1961873]

3. Compounds: GSK PKIS; Assays: UNC Frye lab,  [10.6019/CHEMBL2007661]

4. PubChem BioAssay data set, 

5. Data associated with the publication PLoS ONE, 8(3), e57888, (2013) PMID: 23505445. Compounds: GSK PKIS; Assays: NIH NCATS, 

6. Guccione M, Ettari R, Taliani S, Da Settimo F, Zappalà M, Grasso S..  (2016)  G-Protein-Coupled Receptor Kinase 2 (GRK2) Inhibitors: Current Trends and Future Perspectives.,  59  (20): [PMID:27362616] [10.1021/acs.jmedchem.5b01939]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• GSK Published Kinase Inhibitor Set