ID: ALA2321962

Max Phase: Preclinical

Molecular Formula: C17H10BrN3O4

Molecular Weight: 400.19

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C1Nc2c(Br)cccc2/C1=C1/Nc2cc(C(=O)O)ccc2/C1=N\O

Standard InChI:  InChI=1S/C17H10BrN3O4/c18-10-3-1-2-9-12(16(22)20-13(9)10)15-14(21-25)8-5-4-7(17(23)24)6-11(8)19-15/h1-6,19,25H,(H,20,22)(H,23,24)/b15-12-,21-14+

Standard InChI Key:  GGOSCGOWOVGYLY-HQMCVCOQSA-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: 400.19

Molecular Weight (Monoisotopic): 398.9855

AlogP: 3.11

#Rotatable Bonds: 1

Polar Surface Area: 111.02

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 4.53

CX Basic pKa:

CX LogP: 2.22

CX LogD: -1.07

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.33

Np Likeness Score: 0.05

References

1. 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]

2. Pergola C, Gaboriaud-Kolar N, Jestädt N, König S, Kritsanida M, Schaible AM, Li H, Garscha U, Weinigel C, Barz D, Albring KF, Huber O, Skaltsounis AL, Werz O..  (2014)  Indirubin core structure of glycogen synthase kinase-3 inhibitors as novel chemotype for intervention with 5-lipoxygenase.,  57  (9): [PMID:24697244] [10.1021/jm401740w]

3. Gaboriaud-Kolar N, Myrianthopoulos V, Vougogiannopoulou K, Gerolymatos P, Horne DA, Jove R, Mikros E, Nam S, Skaltsounis AL..  (2016)  Natural-Based Indirubins Display Potent Cytotoxicity toward Wild-Type and T315I-Resistant Leukemia Cell Lines.,  79  (10): [PMID:27726390] [10.1021/acs.jnatprod.6b00285]

Source

Source(1):

• Scientific Literature