5'-Fluoro-1H,1'H-[2,3']biindolylidene-3,2'-dione 3-oxime

ID: ALA1077291

Chembl Id: CHEMBL1077291

Max Phase: Preclinical

Molecular Formula: C16H10FN3O2

Molecular Weight: 295.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1Nc2ccc(F)cc2/C1=C1/Nc2ccccc2/C1=N\O

Standard InChI:  InChI=1S/C16H10FN3O2/c17-8-5-6-12-10(7-8)13(16(21)19-12)15-14(20-22)9-3-1-2-4-11(9)18-15/h1-7,18,22H,(H,19,21)/b15-13-,20-14+

Standard InChI Key:  RJIBTAMXAXHIAN-WAVHTBQISA-N

Alternative Forms

1. Parent:

   

   ALA1077291

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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: 295.27

Molecular Weight (Monoisotopic): 295.0757

AlogP: 2.79

#Rotatable Bonds: ┄

Polar Surface Area: 73.72

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.92

CX Basic pKa: 0.99

CX LogP: 1.94

CX LogD: 1.34

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.40

Np Likeness Score: -0.26

References

1. Choi SJ, Moon MJ, Lee SD, Choi SU, Han SY, Kim YC..  (2010)  Indirubin derivatives as potent FLT3 inhibitors with anti-proliferative activity of acute myeloid leukemic cells.,  20  (6): [PMID:20153646] [10.1016/j.bmcl.2010.01.039]

2. Krivogorsky B, Grundt P, Yolken R, Jones-Brando L..  (2008)  Inhibition of Toxoplasma gondii by indirubin and tryptanthrin analogs.,  52  (12): [PMID:18824607] [10.1128/aac.00903-08]

3. PubChem BioAssay data set, 

4. Jung ME, Byun BJ, Kim HM, Lee JY, Park JH, Lee N, Son YH, Choi SU, Yang KM, Kim SJ, Lee K, Kim YC, Choi G..  (2016)  Discovery of indirubin derivatives as new class of DRAK2 inhibitors from high throughput screening.,  26  (11): [PMID:27106709] [10.1016/j.bmcl.2016.03.111]

5. Ichimaru Y, Fujii T, Saito H, Sano M, Uchiyama T, Miyairi S..  (2017)  5-Bromoindirubin 3'-(O-oxiran-2-ylmethyl)oxime: A long-acting anticancer agent and a suicide inhibitor for epoxide hydrolase.,  25  (17): [PMID:28743492] [10.1016/j.bmc.2017.07.009]

6. Wang H, Wang Z, Wei C, Wang J, Xu Y, Bai G, Yao Q, Zhang L, Chen Y..  (2021)  Anticancer potential of indirubins in medicinal chemistry: Biological activity, structural modification, and structure-activity relationship.,  223  [PMID:34161865] [10.1016/j.ejmech.2021.113652]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays