5-Bromoindirubin

Identification

Generic Name
5-Bromoindirubin
DrugBank Accession Number
DB07493
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 341.159
Monoisotopic: 339.984740189
Chemical Formula
C16H9BrN2O2
Synonyms
  • (2Z)-5'-bromo-2,3'-biindole-2',3(1H,1'H)-dione ammoniate

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCyclin-dependent kinase 2Not 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
Not Available

Interactions

Drug Interactions
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
Not Available
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
Aryl ketones / Secondary alkylarylamines / Benzenoids / Aryl bromides / Vinylogous amides / Secondary carboxylic acid amides / Lactams / Amino acids and derivatives / Enamines / Azacyclic compounds
show 4 more
Substituents
Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl bromide / Aryl halide / Aryl ketone / Azacycle / Benzenoid / Carbonyl group / Carboxamide group
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
60874-72-8
InChI Key
IEQQJQHHJMQETK-YPKPFQOOSA-N
InChI
InChI=1S/C16H9BrN2O2/c17-8-5-6-12-10(7-8)13(16(21)19-12)14-15(20)9-3-1-2-4-11(9)18-14/h1-7,18H,(H,19,21)/b14-13-
IUPAC Name
(Z)-5'-bromo-1',2'-dihydro-1H,3H-[2,3'-biindolylidene]-2',3-dione
SMILES
[H]N1C(=O)\C(C2=C1C=CC(Br)=C2)=C1/N([H])C2=CC=CC=C2C1=O

References

General References
Not Available
PubChem Compound
5287845
PubChem Substance
99443964
ChemSpider
4450135
BindingDB
50142632
ChEMBL
CHEMBL1231469
ZINC
ZINC000100035566
PDBe Ligand
BRY
PDB Entries
2bhe

Clinical Trials

Clinical Trials
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
logP3.2Chemaxon
pKa (Strongest Acidic)10.8Chemaxon
pKa (Strongest Basic)-2.6Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area58.2 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity86.62 m3·mol-1Chemaxon
Polarizability30.99 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8808
Caco-2 permeable-0.5127
P-glycoprotein substrateNon-substrate0.5873
P-glycoprotein inhibitor IInhibitor0.6312
P-glycoprotein inhibitor IIInhibitor0.5875
Renal organic cation transporterNon-inhibitor0.8527
CYP450 2C9 substrateNon-substrate0.8171
CYP450 2D6 substrateNon-substrate0.843
CYP450 3A4 substrateSubstrate0.5092
CYP450 1A2 substrateInhibitor0.8979
CYP450 2C9 inhibitorInhibitor0.805
CYP450 2D6 inhibitorNon-inhibitor0.7569
CYP450 2C19 inhibitorInhibitor0.6649
CYP450 3A4 inhibitorNon-inhibitor0.5571
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9684
Ames testNon AMES toxic0.5323
CarcinogenicityNon-carcinogens0.8647
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.2745 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9797
hERG inhibition (predictor II)Non-inhibitor0.591
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-MSsplash10-03di-1239000000-8761cd455fbdbbbd6845
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-fb1b5a7dbfaedb234aa2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0109000000-1078488290e641b20e4d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-ee96ac4c3d09c3817fbf
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-3009000000-e0cf66af92dd062e69cb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01qa-0493000000-3d5ded6cd1d1d7de132c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9100000000-2453401b604fd19e7578
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]-166.45995
predicted
DeepCCS 1.0 (2019)
[M+H]+168.81795
predicted
DeepCCS 1.0 (2019)
[M+Na]+175.53114
predicted
DeepCCS 1.0 (2019)

Targets

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Details
1. Cyclin-dependent kinase 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Serine/threonine-protein kinase involved in the control of the cell cycle; essential for meiosis, but dispensable for mitosis. Phosphorylates CTNNB1, USP37, p53/TP53, NPM1, CDK7, RB1, BRCA2, MYC, N...
Gene Name
CDK2
Uniprot ID
P24941
Uniprot Name
Cyclin-dependent kinase 2
Molecular Weight
33929.215 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 September 15, 2010 21:22 / Updated at June 12, 2020 16:52