7-bromo-indirubin-3'-oxime

ID: ALA1092509

Chembl Id: CHEMBL1092509

Max Phase: Preclinical

Molecular Formula: C16H10BrN3O2

Molecular Weight: 356.18

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

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

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/h1-7,18,22H,(H,19,21)/b15-12-,20-14+

Standard InChI Key:  VJTWDKLJCDHHRX-FQJRYBMTSA-N

Alternative Forms

  1. Parent:

    ALA1092509

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Associated Targets(Human)

ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SH-SY5Y (11521 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-MEL-28 (48833 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LoVo (4724 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KCL-22 (265 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HepG2 (196354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CDK5 Tchem Cyclin-dependent kinase 5/CDK5 activator 1 (3697 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AURKA Tchem Serine/threonine-protein kinase Aurora-A (10240 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AURKB Tchem Serine/threonine-protein kinase Aurora-B (6805 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AURKC Tchem Serine/threonine-protein kinase Aurora-C (1780 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

GSK3-beta Glycogen synthase kinase-3 (925 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Klebsiella pneumoniae (43867 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 356.18Molecular Weight (Monoisotopic): 354.9956AlogP: 3.42#Rotatable Bonds: 0
Polar Surface Area: 73.72Molecular Species: NEUTRALHBA: 4HBD: 3
#RO5 Violations: 0HBA (Lipinski): 5HBD (Lipinski): 3#RO5 Violations (Lipinski): 0
CX Acidic pKa: 6.89CX Basic pKa: 0.96CX LogP: 2.56CX LogD: 1.94
Aromatic Rings: 2Heavy Atoms: 22QED Weighted: 0.38Np Likeness Score: 0.15

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. 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]
5. 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]
6. 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