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

ID: ALA107061

Chembl Id: CHEMBL107061

PubChem CID: 44336128

Max Phase: Preclinical

Molecular Formula: C21H21N3O5S

Molecular Weight: 427.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)c(/C=C1\C(=O)Nc3ccc(S(N)(=O)=O)cc31)cn2CCCO

Standard InChI:  InChI=1S/C21H21N3O5S/c1-29-14-3-6-20-16(10-14)13(12-24(20)7-2-8-25)9-18-17-11-15(30(22,27)28)4-5-19(17)23-21(18)26/h3-6,9-12,25H,2,7-8H2,1H3,(H,23,26)(H2,22,27,28)/b18-9-

Standard InChI Key:  UCMHGBCESZOZPQ-NVMNQCDNSA-N

Alternative Forms

1. Parent:

   

   ALA107061

   3-((1-(3-hydroxypropyl)-5-methoxy-1H-indol-3-yl)methylene)-2-oxoindoline-5-sulfonamide

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: 427.48

Molecular Weight (Monoisotopic): 427.1202

AlogP: 2.17

#Rotatable Bonds: 6

Polar Surface Area: 123.65

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.05

CX Basic pKa: ┄

CX LogP: 1.41

CX LogD: 1.41

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.52

Np Likeness Score: -1.25

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]

Source

Source(1):

• Scientific Literature