4-{5-Methoxy-3-[2-oxo-5-sulfamoyl-1,2-dihydro-indol-(3Z)-ylidenemethyl]-indol-1-yl}-butyramide

ID: ALA431645

Chembl Id: CHEMBL431645

PubChem CID: 44335814

Max Phase: Preclinical

Molecular Formula: C22H22N4O5S

Molecular Weight: 454.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)c(/C=C1\C(=O)Nc3ccc(S(N)(=O)=O)cc31)cn2CCCC(N)=O

Standard InChI:  InChI=1S/C22H22N4O5S/c1-31-14-4-7-20-16(10-14)13(12-26(20)8-2-3-21(23)27)9-18-17-11-15(32(24,29)30)5-6-19(17)25-22(18)28/h4-7,9-12H,2-3,8H2,1H3,(H2,23,27)(H,25,28)(H2,24,29,30)/b18-9-

Standard InChI Key:  YJHSHAAGDWUFBT-NVMNQCDNSA-N

Alternative Forms

1. Parent:

   

   ALA431645

   4-[5-methoxy-3-[(Z)-(2-oxo-5-sulfamoyl-1H-indol-3-ylidene)methyl]indol-1-yl]butanamide

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: 454.51

Molecular Weight (Monoisotopic): 454.1311

AlogP: 2.06

#Rotatable Bonds: 7

Polar Surface Area: 146.51

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.05

CX Basic pKa: ┄

CX LogP: 1.23

CX LogD: 1.23

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.47

Np Likeness Score: -1.37

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

Source

Source(1):

• Scientific Literature