Indirubin-3'-Monoxime

Identification

Name
Indirubin-3'-Monoxime
Accession Number
DB02052  (EXPT01949)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 277.2774
Monoisotopic: 277.085126611
Chemical Formula
C16H11N3O2
InChI Key
HBDSHCUSXQATPO-BGBJRWHRSA-N
InChI
InChI=1S/C16H11N3O2/c20-16-13(9-5-1-3-7-11(9)18-16)15-14(19-21)10-6-2-4-8-12(10)17-15/h1-8,17,21H,(H,18,20)/b15-13-,19-14+
IUPAC Name
3-[(2Z,3E)-3-(hydroxyimino)-2,3-dihydro-1H-indol-2-ylidene]-2,3-dihydro-1H-indol-2-one
SMILES
O\N=C1\C(\NC2=C\1C=CC=C2)=C1\C(=O)NC2=C1C=CC=C2

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlycogen synthase kinase-3 betaNot AvailableHuman
UCyclin-dependent kinase 5
inhibitor
Human
UCyclin-dependent kinase 1
binder
Human
UCyclin-dependent kinase 5 activator 1Not AvailableHuman
UCyclin-dependent kinase 2
inhibitor
Human
UAryl hydrocarbon receptor
agonist
Human
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
5326739
PubChem Substance
46507166
ChemSpider
21105558
BindingDB
7393
ChEBI
43645
ChEMBL
CHEMBL216543
Therapeutic Targets Database
DNC000796
HET
IXM
PDB Entries
1q41 / 1unh / 2qkr

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.117 mg/mLALOGPS
logP2.18ALOGPS
logP1.79ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)8.31ChemAxon
pKa (Strongest Basic)1.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.72 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity82.82 m3·mol-1ChemAxon
Polarizability28.92 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9903
Blood Brain Barrier+0.8515
Caco-2 permeable-0.5517
P-glycoprotein substrateNon-substrate0.5516
P-glycoprotein inhibitor INon-inhibitor0.6149
P-glycoprotein inhibitor IINon-inhibitor0.5081
Renal organic cation transporterNon-inhibitor0.8439
CYP450 2C9 substrateNon-substrate0.7492
CYP450 2D6 substrateNon-substrate0.8283
CYP450 3A4 substrateSubstrate0.5314
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorInhibitor0.5566
CYP450 2D6 inhibitorInhibitor0.5933
CYP450 2C19 inhibitorInhibitor0.7879
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.959
Ames testNon AMES toxic0.5118
CarcinogenicityNon-carcinogens0.7205
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4357 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9799
hERG inhibition (predictor II)Non-inhibitor0.7591
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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 / Ketoximes / Cyclic carboximidic acids / Propargyl-type 1,3-dipolar organic compounds / Enamines / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Hydrocarbon derivatives
Substituents
Dihydroindole / Secondary aliphatic/aromatic amine / Benzenoid / Ketoxime / Cyclic carboximidic acid / Enamine / Secondary amine / Propargyl-type 1,3-dipolar organic compound / Organic 1,3-dipolar compound / Azacycle
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. 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. [PubMed:10592235]
Details
2. Cyclin-dependent kinase 5
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Tau-protein kinase activity
Specific Function
Proline-directed serine/threonine-protein kinase essential for neuronal cell cycle arrest and differentiation and may be involved in apoptotic cell death in neuronal diseases by triggering abortive...
Gene Name
CDK5
Uniprot ID
Q00535
Uniprot Name
Cyclin-dependent-like kinase 5
Molecular Weight
33304.125 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. 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. [PubMed:10592235]
Details
3. Cyclin-dependent kinase 1
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Binder
General Function
Rna polymerase ii carboxy-terminal domain kinase activity
Specific Function
Plays a key role in the control of the eukaryotic cell cycle by modulating the centrosome cycle as well as mitotic onset; promotes G2-M transition, and regulates G1 progress and G1-S transition via...
Gene Name
CDK1
Uniprot ID
P06493
Uniprot Name
Cyclin-dependent kinase 1
Molecular Weight
34095.14 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein serine/threonine kinase activator activity
Specific Function
p35 is a neuron specific activator of CDK5. The complex p35/CDK5 is required for neurite outgrowth and cortical lamination. Involved in dendritic spine morphogenesis by mediating the EFNA1-EPHA4 si...
Gene Name
CDK5R1
Uniprot ID
Q15078
Uniprot Name
Cyclin-dependent kinase 5 activator 1
Molecular Weight
34059.85 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. [PubMed:10592235]
Details
5. Cyclin-dependent kinase 2
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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. [PubMed:10592235]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Transcription regulatory region dna binding
Specific Function
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes...
Gene Name
AHR
Uniprot ID
P35869
Uniprot Name
Aryl hydrocarbon receptor
Molecular Weight
96146.705 Da
References
  1. Peter Guengerich F, Martin MV, McCormick WA, Nguyen LP, Glover E, Bradfield CA: Aryl hydrocarbon receptor response to indigoids in vitro and in vivo. Arch Biochem Biophys. 2004 Mar 15;423(2):309-16. [PubMed:15001395]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 14:52