3-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-4-[1-(3-hydroxy-propyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-pyrrole-2,5-dione

ID: ALA111620

Chembl Id: CHEMBL111620

PubChem CID: 10366534

Max Phase: Preclinical

Molecular Formula: C20H14ClF3N4O3

Molecular Weight: 450.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)C(c2cn(CCCO)c3ncccc23)=C1c1ncc(C(F)(F)F)cc1Cl

Standard InChI:  InChI=1S/C20H14ClF3N4O3/c21-13-7-10(20(22,23)24)8-26-16(13)15-14(18(30)27-19(15)31)12-9-28(5-2-6-29)17-11(12)3-1-4-25-17/h1,3-4,7-9,29H,2,5-6H2,(H,27,30,31)

Standard InChI Key:  WFTBLYUVDBPJAV-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA111620

   3-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-4-[1-(3-hydroxy-propyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-pyrrole-2,5-dione

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: 450.80

Molecular Weight (Monoisotopic): 450.0707

AlogP: 3.05

#Rotatable Bonds: 5

Polar Surface Area: 97.11

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.65

CX Basic pKa: 3.43

CX LogP: 2.19

CX LogD: 2.19

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.58

Np Likeness Score: -0.91

References

1. Zhang HC, Ye H, Conway BR, Derian CK, Addo MF, Kuo GH, Hecker LR, Croll DR, Li J, Westover L, Xu JZ, Look R, Demarest KT, Andrade-Gordon P, Damiano BP, Maryanoff BE..  (2004)  3-(7-Azaindolyl)-4-arylmaleimides as potent, selective inhibitors of glycogen synthase kinase-3.,  14  (12): [PMID:15149684] [10.1016/j.bmcl.2004.03.090]

2. Saraswati AP, Ali Hussaini SM, Krishna NH, Babu BN, Kamal A..  (2018)  Glycogen synthase kinase-3 and its inhibitors: Potential target for various therapeutic conditions.,  144  [PMID:29306837] [10.1016/j.ejmech.2017.11.103]

3. Xu M, Wang SL, Zhu L, Wu PY, Dai WB, Rakesh KP..  (2019)  Structure-activity relationship (SAR) studies of synthetic glycogen synthase kinase-3β inhibitors: A critical review.,  164  [PMID:30616053] [10.1016/j.ejmech.2018.12.073]

Source

Source(1):

• Scientific Literature