NAV

6-bromoindirubin-3'-oxime

Identification

Generic Name
6-bromoindirubin-3'-oxime
DrugBank Accession Number
DB03444
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 356.174
Monoisotopic: 354.995639226
Chemical Formula
C16H10BrN3O2
Synonyms
  • (2Z,3E)-6-Bromoindirubin-3'-oxime
  • (2Z,3E)-6'-bromo-2,3'-biindole-2',3(1H,1'H)-dione 3-oxime
  • 6-BIO
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGlycogen synthase kinase-3 betaNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as indolines. These are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indolines
Direct Parent
Indolines
Alternative Parents
Secondary alkylarylamines / Benzenoids / Aryl bromides / Vinylogous amides / Ketoximes / Secondary carboxylic acid amides / Lactams / Amino acids and derivatives / Enamines / Azacyclic compounds
show 5 more
Substituents
Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl bromide / Aryl halide / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organobromine compound, oxindole, ketoxime, biindole (CHEBI:86290)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
667463-62-9
InChI Key
DDLZLOKCJHBUHD-WAVHTBQISA-N
InChI
InChI=1S/C16H10BrN3O2/c17-8-5-6-9-12(7-8)19-16(21)13(9)15-14(20-22)10-3-1-2-4-11(10)18-15/h1-7,18,22H,(H,19,21)/b15-13-,20-14+
IUPAC Name
(Z,3E)-6'-bromo-3-(hydroxyimino)-1',2'-dihydro-1H,3H-[2,3'-biindolyliden]-2'-one
SMILES
O\N=C1\C(\NC2=C\1C=CC=C2)=C1\C(=O)NC2=CC(Br)=CC=C12

References

General References
Not Available
PubChem Compound
5287844
PubChem Substance
46507596
ChemSpider
21171550
BindingDB
50012188
ChEBI
86290
ChEMBL
CHEMBL409450
ZINC
ZINC000018128386
PDBe Ligand
BRW
PDB Entries
1uv5

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0341 mg/mLALOGPS
logP2.99ALOGPS
logP2.56Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)6.89Chemaxon
pKa (Strongest Basic)0.96Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area73.72 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity90.44 m3·mol-1Chemaxon
Polarizability32.76 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.988
Blood Brain Barrier+0.8265
Caco-2 permeable-0.5532
P-glycoprotein substrateNon-substrate0.55
P-glycoprotein inhibitor INon-inhibitor0.5652
P-glycoprotein inhibitor IIInhibitor0.5423
Renal organic cation transporterNon-inhibitor0.828
CYP450 2C9 substrateNon-substrate0.7959
CYP450 2D6 substrateNon-substrate0.8323
CYP450 3A4 substrateSubstrate0.552
CYP450 1A2 substrateInhibitor0.8824
CYP450 2C9 inhibitorInhibitor0.6297
CYP450 2D6 inhibitorNon-inhibitor0.6051
CYP450 2C19 inhibitorInhibitor0.7068
CYP450 3A4 inhibitorInhibitor0.8517
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.979
Ames testNon AMES toxic0.5385
CarcinogenicityNon-carcinogens0.6881
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4574 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.982
hERG inhibition (predictor II)Non-inhibitor0.735
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-004i-1119000000-dfa582be1fe6e62bda41
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-cae46b19d95473f427c6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-7c37c5630469b57a06fe
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-65853c3abdb4d64a7ed4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ufr-2009000000-19b7246068274b645344
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0619000000-3adfda2da8ee5e83609e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9002000000-7c0c7f907f0e705a092e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-169.34508
predicted
DeepCCS 1.0 (2019)
[M+H]+171.70308
predicted
DeepCCS 1.0 (2019)
[M+Na]+178.62099
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Glycogen synthase kinase-3 beta
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ubiquitin protein ligase binding
Specific Function
Constitutively active protein kinase that acts as a negative regulator in the hormonal control of glucose homeostasis, Wnt signaling and regulation of transcription factors and microtubules, by pho...
Gene Name
GSK3B
Uniprot ID
P49841
Uniprot Name
Glycogen synthase kinase-3 beta
Molecular Weight
46743.865 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52