3-Phenyl-4-phenylamino-pyrrole-2,5-dione

ID: ALA346551

Chembl Id: CHEMBL346551

PubChem CID: 6539451

Max Phase: Preclinical

Molecular Formula: C16H12N2O2

Molecular Weight: 264.28

Molecule Type: Small molecule

Names and Identifiers

Synonyms: SKF-62604 | SKF-62604 | SKF-62604|4-arylmaleimide deriv. 6a|phenyl anilino-maleimide|BDBM8218|CHEMBL346551|SCHEMBL5682682|HMS3303J01|HMS3305A03|NSC756495|NSC-756495|NCGC00241898-01|AB01092118-01|3-phenyl-4-(phenylamino)-2,5-dihydro-1H-pyrrole-2,5-dione

Canonical SMILES:  O=C1NC(=O)C(c2ccccc2)=C1Nc1ccccc1

Standard InChI:  InChI=1S/C16H12N2O2/c19-15-13(11-7-3-1-4-8-11)14(16(20)18-15)17-12-9-5-2-6-10-12/h1-10H,(H2,17,18,19,20)

Standard InChI Key:  ACQZMAJVOPRMQJ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA346551

   4-Arylmaleimide deriv. 6a

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: 264.28

Molecular Weight (Monoisotopic): 264.0899

AlogP: 2.17

#Rotatable Bonds: 3

Polar Surface Area: 58.20

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.58

CX Basic pKa: ┄

CX LogP: 1.95

CX LogD: 1.94

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.84

Np Likeness Score: -0.21

References

1. Smith DG, Buffet M, Fenwick AE, Haigh D, Ife RJ, Saunders M, Slingsby BP, Stacey R, Ward RW..  (2001)  3-Anilino-4-arylmaleimides: potent and selective inhibitors of glycogen synthase kinase-3 (GSK-3).,  11  (5): [PMID:11266159] [10.1016/s0960-894x(00)00721-6]

2. Kim HJ, Choo H, Cho YS, No KT, Pae AN..  (2008)  Novel GSK-3beta inhibitors from sequential virtual screening.,  16  (2): [PMID:18006321] [10.1016/j.bmc.2007.10.047]

3. Taha MO, Bustanji Y, Al-Ghussein MA, Mohammad M, Zalloum H, Al-Masri IM, Atallah N..  (2008)  Pharmacophore modeling, quantitative structure-activity relationship analysis, and in silico screening reveal potent glycogen synthase kinase-3beta inhibitory activities for cimetidine, hydroxychloroquine, and gemifloxacin.,  51  (7): [PMID:18324764] [10.1021/jm7009765]

4. PubChem BioAssay data set, 

5. Compounds: GSK PKIS; Assays: Nanosyn kinase panel,  [10.6019/CHEMBL1961873]

6. Compounds: GSK PKIS; Assays: UNC Frye lab,  [10.6019/CHEMBL2007661]

7. Data associated with the publication PLoS ONE, 8(3), e57888, (2013) PMID: 23505445. Compounds: GSK PKIS; Assays: NIH NCATS, 

8. Wells CI, Kapadia NR, Couñago RM, Drewry DH..  (2018)  In depth analysis of kinase cross screening data to identify chemical starting points for inhibition of the Nek family of kinases.,  9  (1): [PMID:30108900] [10.1039/C7MD00510E]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• GSK Published Kinase Inhibitor Set