N-(1,2-Dimethyl-1H-indol-3-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-acrylamide

ID: ALA297636

Chembl Id: CHEMBL297636

PubChem CID: 6539898

Max Phase: Preclinical

Molecular Formula: C23H24N4O2

Molecular Weight: 388.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(CN(C)C(=O)/C=C/c2cnc3c(c2)CCC(=O)N3)c2ccccc2n1C

Standard InChI:  InChI=1S/C23H24N4O2/c1-15-19(18-6-4-5-7-20(18)27(15)3)14-26(2)22(29)11-8-16-12-17-9-10-21(28)25-23(17)24-13-16/h4-8,11-13H,9-10,14H2,1-3H3,(H,24,25,28)/b11-8+

Standard InChI Key:  PVNPCRMKZHRPEV-DHZHZOJOSA-N

Alternative Forms

1. Parent:

   

   ALA297636

   (2e)-N-[(1,2-Dimethyl-1h-Indol-3-Yl)methyl]-N-Methyl-3-(7-Oxo-5,6,7,8-Tetrahydro-1,8-Naphthyridin-3-Yl)prop-2-Enamide

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: 388.47

Molecular Weight (Monoisotopic): 388.1899

AlogP: 3.44

#Rotatable Bonds: 4

Polar Surface Area: 67.23

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.03

CX Basic pKa: 3.57

CX LogP: 2.94

CX LogD: 2.94

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.70

Np Likeness Score: -0.74

References

1. Seefeld MA, Miller WH, Newlander KA, Burgess WJ, DeWolf WE, Elkins PA, Head MS, Jakas DR, Janson CA, Keller PM, Manley PJ, Moore TD, Payne DJ, Pearson S, Polizzi BJ, Qiu X, Rittenhouse SF, Uzinskas IN, Wallis NG, Huffman WF..  (2003)  Indole naphthyridinones as inhibitors of bacterial enoyl-ACP reductases FabI and FabK.,  46  (9): [PMID:12699381] [10.1021/jm0204035]

2. Štular T,Lešnik S,Rožman K,Schink J,Zdouc M,Ghysels A,Liu F,Aldrich CC,Haupt VJ,Salentin S,Daminelli S,Schroeder M,Langer T,Gobec S,Janežič D,Konc J.  (2016)  Discovery of Mycobacterium tuberculosis InhA Inhibitors by Binding Sites Comparison and Ligands Prediction.,  59  (24.0): [PMID:27936766] [10.1021/acs.jmedchem.6b01277]

3. Rana P, Ghouse SM, Akunuri R, Madhavi YV, Chopra S, Nanduri S..  (2020)  FabI (enoyl acyl carrier protein reductase) - A potential broad spectrum therapeutic target and its inhibitors.,  208  [PMID:32883635] [10.1016/j.ejmech.2020.112757]

Source

Source(1):

• Scientific Literature