3-[1-(1-Methyl-1H-indol-3-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid amide

ID: ALA104279

Chembl Id: CHEMBL104279

Cas Number: 622387-85-3

PubChem CID: 6419747

Max Phase: Preclinical

Molecular Formula: C18H15N3O3S

Molecular Weight: 353.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(/C=C2\C(=O)Nc3ccc(S(N)(=O)=O)cc32)c2ccccc21

Standard InChI:  InChI=1S/C18H15N3O3S/c1-21-10-11(13-4-2-3-5-17(13)21)8-15-14-9-12(25(19,23)24)6-7-16(14)20-18(15)22/h2-10H,1H3,(H,20,22)(H2,19,23,24)/b15-8-

Standard InChI Key:  MLKHXLFEYOOYEY-NVNXTCNLSA-N

Alternative Forms

1. Parent:

   

   ALA104279

   Syk Inhibitor

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: 353.40

Molecular Weight (Monoisotopic): 353.0834

AlogP: 2.32

#Rotatable Bonds: 2

Polar Surface Area: 94.19

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.05

CX Basic pKa: ┄

CX LogP: 2.19

CX LogD: 2.19

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.69

Np Likeness Score: -1.24

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. Chu JJ, Yang PL..  (2007)  c-Src protein kinase inhibitors block assembly and maturation of dengue virus.,  104  (9): [PMID:17360676] [10.1073/pnas.0611681104]

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. Gao Y, Davies SP, Augustin M, Woodward A, Patel UA, Kovelman R, Harvey KJ..  (2013)  A broad activity screen in support of a chemogenomic map for kinase signalling research and drug discovery.,  451  (2): [PMID:23398362] [10.1042/bj20121418]

5. Tammiku-Taul J,Park R,Jaanson K,Luberg K,Dobchev DA,Kananovich D,Noole A,Mandel M,Kaasik A,Lopp M,Timmusk T,Karelson M.  (2016)  Indole-like Trk receptor antagonists.,  121  [PMID:27318978] [10.1016/j.ejmech.2016.06.003]

Source

Source(1):

• Scientific Literature