ID: ALA485053

Max Phase: Preclinical

Molecular Formula: C12H11N3O3

Molecular Weight: 245.24

Molecule Type: Small molecule

Representations

Canonical SMILES:  CN1C(=O)/C(=C/c2ccc3c(c2)OCO3)N=C1N

Standard InChI:  InChI=1S/C12H11N3O3/c1-15-11(16)8(14-12(15)13)4-7-2-3-9-10(5-7)18-6-17-9/h2-5H,6H2,1H3,(H2,13,14)/b8-4-

Standard InChI Key:  PKEDBIGNILOTHW-YWEYNIOJSA-N

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

Properties

Molecular Weight: 245.24

Molecular Weight (Monoisotopic): 245.0800

AlogP: 0.54

#Rotatable Bonds: 1

Polar Surface Area: 77.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 2.14

CX LogP: 0.59

CX LogD: 0.59

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.73

Np Likeness Score: -0.04

References

1. Chan GW, Mong S, Hemling ME, Freyer AJ, Offen PH, DeBrosse CW, Sarau HM, Westley JW..  (1993)  New leukotriene B4 receptor antagonist: leucettamine A and related imidazole alkaloids from the marine sponge Leucetta microraphis.,  56  (1): [PMID:8383730] [10.1021/np50100a005]

2. Debdab M, Renault S, Lozach O, Meijer L, Paquin L, Carreaux F, Bazureau JP..  (2010)  Synthesis and preliminary biological evaluation of new derivatives of the marine alkaloid leucettamine B as kinase inhibitors.,  45  (2): [PMID:19879673] [10.1016/j.ejmech.2009.10.009]

3. Debdab M, Carreaux F, Renault S, Soundararajan M, Fedorov O, Filippakopoulos P, Lozach O, Babault L, Tahtouh T, Baratte B, Ogawa Y, Hagiwara M, Eisenreich A, Rauch U, Knapp S, Meijer L, Bazureau JP..  (2011)  Leucettines, a class of potent inhibitors of cdc2-like kinases and dual specificity, tyrosine phosphorylation regulated kinases derived from the marine sponge leucettamine B: modulation of alternative pre-RNA splicing.,  54  (12): [PMID:21615147] [10.1021/jm200274d]

4. Tahtouh T, Elkins JM, Filippakopoulos P, Soundararajan M, Burgy G, Durieu E, Cochet C, Schmid RS, Lo DC, Delhommel F, Oberholzer AE, Pearl LH, Carreaux F, Bazureau JP, Knapp S, Meijer L..  (2012)  Selectivity, cocrystal structures, and neuroprotective properties of leucettines, a family of protein kinase inhibitors derived from the marine sponge alkaloid leucettamine B.,  55  (21): [PMID:22998443] [10.1021/jm301034u]

5. Tahtouh T, Durieu E, Villiers B, Bruyère C, Nguyen TL, Fant X, Ahn KH, Khurana L, Deau E, Lindberg MF, Sévère E, Miege F, Roche D, Limanton E, L'Helgoual'ch JM, Burgy G, Guiheneuf S, Herault Y, Kendall DA, Carreaux F, Bazureau JP, Meijer L..  (2022)  Structure-Activity Relationship in the Leucettine Family of Kinase Inhibitors.,  65  (2.0): [PMID:34928152] [10.1021/acs.jmedchem.1c01141]

6. Qin Z, Qin L, Feng X, Li Z, Bian J..  (2021)  Development of Cdc2-like Kinase 2 Inhibitors: Achievements and Future Directions.,  64  (18.0): [PMID:34519506] [10.1021/acs.jmedchem.1c00985]

7. Lindberg MF, Deau E, Arfwedson J, George N, George P, Alfonso P, Corrionero A, Meijer L..  (2023)  Comparative Efficacy and Selectivity of Pharmacological Inhibitors of DYRK and CLK Protein Kinases.,  66  (6): [PMID:36876904] [10.1021/acs.jmedchem.2c02068]

Source

Source(1):

• Scientific Literature