(3-{3-[4-(2-Methoxy-phenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-pyrrolo[2,3-b]pyridin-1-yl}-propyl)-carbamic acid tert-butyl ester

ID: ALA109981

Chembl Id: CHEMBL109981

PubChem CID: 10073694

Max Phase: Preclinical

Molecular Formula: C26H28N4O5

Molecular Weight: 476.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1C1=C(c2cn(CCCNC(=O)OC(C)(C)C)c3ncccc23)C(=O)NC1=O

Standard InChI:  InChI=1S/C26H28N4O5/c1-26(2,3)35-25(33)28-13-8-14-30-15-18(16-10-7-12-27-22(16)30)21-20(23(31)29-24(21)32)17-9-5-6-11-19(17)34-4/h5-7,9-12,15H,8,13-14H2,1-4H3,(H,28,33)(H,29,31,32)

Standard InChI Key:  MJSXSLBYCSPRHR-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA109981

   (3-{3-[4-(2-Methoxy-phenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-pyrrolo[2,3-b]pyridin-1-yl}-propyl)-carbamic acid tert-butyl ester

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: 476.53

Molecular Weight (Monoisotopic): 476.2060

AlogP: 3.53

#Rotatable Bonds: 7

Polar Surface Area: 111.55

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.71

CX Basic pKa: 3.84

CX LogP: 2.77

CX LogD: 2.77

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.40

Np Likeness Score: -0.73

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