ID: ALA373834

Max Phase: Preclinical

Molecular Formula: C16H10BrN3O2

Molecular Weight: 356.18

Molecule Type: Small molecule

Representations

Synonyms (1): 7-Bromoindirubin-3'Oxime
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=Nc1c(-c2c(O)[nH]c3c(Br)cccc23)[nH]c2ccccc12

Standard InChI:  InChI=1S/C16H10BrN3O2/c17-10-6-3-5-9-12(16(21)19-13(9)10)15-14(20-22)8-4-1-2-7-11(8)18-15/h1-7,18-19,21H

Standard InChI Key:  HYMACPDEJIEMST-UHFFFAOYSA-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: 356.18

Molecular Weight (Monoisotopic): 354.9956

AlogP: 5.18

#Rotatable Bonds: 2

Polar Surface Area: 81.24

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.27

CX Basic pKa:

CX LogP: 4.37

CX LogD: 4.32

Aromatic Rings: 4

Heavy Atoms: 22

QED Weighted: 0.43

Np Likeness Score: 0.29

References

1. Ferandin Y, Bettayeb K, Kritsanida M, Lozach O, Polychronopoulos P, Magiatis P, Skaltsounis AL, Meijer L..  (2006)  3'-Substituted 7-halogenoindirubins, a new class of cell death inducing agents.,  49  (15): [PMID:16854069] [10.1021/jm060314i]

2. Myrianthopoulos V, Magiatis P, Ferandin Y, Skaltsounis AL, Meijer L, Mikros E..  (2007)  An integrated computational approach to the phenomenon of potent and selective inhibition of aurora kinases B and C by a series of 7-substituted indirubins.,  50  (17): [PMID:17665890] [10.1021/jm070077z]

3. Kritsanida M, Magiatis P, Skaltsounis AL, Peng Y, Li P, Wennogle LP..  (2009)  Synthesis and antiproliferative activity of 7-azaindirubin-3'-oxime, a 7-aza isostere of the natural indirubin pharmacophore.,  72  (12): [PMID:19994845] [10.1021/np9003905]

4. Myrianthopoulos V, Kritsanida M, Gaboriaud-Kolar N, Magiatis P, Ferandin Y, Durieu E, Lozach O, Cappel D, Soundararajan M, Filippakopoulos P, Sherman W, Knapp S, Meijer L, Mikros E, Skaltsounis AL..  (2013)  Novel Inverse Binding Mode of Indirubin Derivatives Yields Improved Selectivity for DYRK Kinases.,  4  (1): [PMID:23336033] [10.1021/ml300207a]

Source

Source(1):

• Scientific Literature