(Z)-7'-Chloro-1H,1'H-[2,3']biindolylidene-3,2'-dione 3-oxime

ID: ALA3265230

Chembl Id: CHEMBL3265230

Max Phase: Preclinical

Molecular Formula: C16H10ClN3O2

Molecular Weight: 311.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1Nc2c(Cl)cccc2/C1=C1/Nc2ccccc2/C1=N\O

Standard InChI:  InChI=1S/C16H10ClN3O2/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/h1-7,18,22H,(H,19,21)/b15-12-,20-14+

Standard InChI Key:  FVVYATOWQXNKDP-FQJRYBMTSA-N

Alternative Forms

1. Parent:

   

   ALA3265230

   ---

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: 311.73

Molecular Weight (Monoisotopic): 311.0462

AlogP: 3.31

#Rotatable Bonds: 0

Polar Surface Area: 73.72

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 6.92

CX Basic pKa: 1.00

CX LogP: 2.40

CX LogD: 1.80

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.40

Np Likeness Score: -0.05

References

1. 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]

2. Evdokimov NM, Magedov IV, McBrayer D, Kornienko A..  (2016)  Isatin derivatives with activity against apoptosis-resistant cancer cells.,  26  (6): [PMID:26883150] [10.1016/j.bmcl.2016.02.015]

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]

4. Li H, Mattingly AE, Smith RD, Melander RJ, Ernst RK, Melander C..  (2023)  6-Bromoindirubin-3'-oxime derivatives are highly active colistin adjuvants against Klebsiella pneumoniae.,  14  (2.0): [PMID:36846374] [10.1039/d2md00370h]

Source

Source(1):

• Scientific Literature