3-[1-(5-Methoxy-1-methyl-1H-indol-3-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid methylamide

ID: ALA318079

Chembl Id: CHEMBL318079

Cas Number: 622388-41-4

PubChem CID: 9820317

Max Phase: Preclinical

Molecular Formula: C21H19N3O3

Molecular Weight: 361.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)c1ccc2c(c1)/C(=C/c1cn(C)c3ccc(OC)cc13)C(=O)N2

Standard InChI:  InChI=1S/C21H19N3O3/c1-22-20(25)12-4-6-18-16(8-12)17(21(26)23-18)9-13-11-24(2)19-7-5-14(27-3)10-15(13)19/h4-11H,1-3H3,(H,22,25)(H,23,26)/b17-9-

Standard InChI Key:  PFAPJAYUYRSASC-MFOYZWKCSA-N

Alternative Forms

1. Parent:

   

   ALA318079

   3-((5-methoxy-1-methyl-1H-indol-3-yl)methylene)-N-methyl-2-oxoindoline-5-carboxamide

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: 361.40

Molecular Weight (Monoisotopic): 361.1426

AlogP: 3.04

#Rotatable Bonds: 3

Polar Surface Area: 72.36

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.94

CX Basic pKa: ┄

CX LogP: 2.50

CX LogD: 2.50

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.70

Np Likeness Score: -0.96

References

1. Lai JY, Cox PJ, Patel R, Sadiq S, Aldous DJ, Thurairatnam S, Smith K, Wheeler D, Jagpal S, Parveen S, Fenton G, Harrison TK, McCarthy C, Bamborough P..  (2003)  Potent small molecule inhibitors of spleen tyrosine kinase (Syk).,  13  (18): [PMID:12941345] [10.1016/s0960-894x(03)00658-9]

2. Xie HZ, Li LL, Ren JX, Zou J, Yang L, Wei YQ, Yang SY..  (2009)  Pharmacophore modeling study based on known spleen tyrosine kinase inhibitors together with virtual screening for identifying novel inhibitors.,  19  (7): [PMID:19254842] [10.1016/j.bmcl.2009.02.049]

3. Singh R, Masuda ES, Payan DG..  (2012)  Discovery and development of spleen tyrosine kinase (SYK) inhibitors.,  55  (8): [PMID:22257213] [10.1021/jm201271b]

4. Kaur M, Singh M, Chadha N, Silakari O..  (2016)  Oxindole: A chemical prism carrying plethora of therapeutic benefits.,  123  [PMID:27543880] [10.1016/j.ejmech.2016.08.011]

Source

Source(1):

• Scientific Literature