(2e,3s)-3-Hydroxy-5'-[(4-Hydroxypiperidin-1-Yl)Sulfonyl]-3-Methyl-1,3-Dihydro-2,3'-Biindol-2'(1'h)-One

Identification

Name
(2e,3s)-3-Hydroxy-5'-[(4-Hydroxypiperidin-1-Yl)Sulfonyl]-3-Methyl-1,3-Dihydro-2,3'-Biindol-2'(1'h)-One
Accession Number
DB03583  (EXPT02828)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 441.5
Monoisotopic: 441.135841551
Chemical Formula
C22H23N3O5S
InChI Key
AYOAIABDFUJDKQ-SQJPUDIVSA-N
InChI
InChI=1S/C22H23N3O5S/c1-22(28)16-4-2-3-5-18(16)23-20(22)19-15-12-14(6-7-17(15)24-21(19)27)31(29,30)25-10-8-13(26)9-11-25/h2-7,12-13,23,26,28H,8-11H2,1H3,(H,24,27)/b20-19-/t22-/m0/s1
IUPAC Name
3-[(2Z,3S)-3-hydroxy-3-methyl-2,3-dihydro-1H-indol-2-ylidene]-5-[(4-hydroxypiperidin-1-yl)sulfonyl]-2,3-dihydro-1H-indol-2-one
SMILES
OC1CCN(CC1)S(=O)(=O)C1=CC2=C(C=C1)NC(=O)\C2=C1/NC2=C(C=CC=C2)[[email protected]]1(C)O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCyclin-dependent kinase 2Not AvailableHuman
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
5289321
PubChem Substance
46506569
ChemSpider
4451312
HET
RYU
PDB Entries
2bhh

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 Solubility0.176 mg/mLALOGPS
logP1.55ALOGPS
logP-0.0056ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)10.55ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area118.97 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity119.83 m3·mol-1ChemAxon
Polarizability45.18 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier-0.8488
Caco-2 permeable-0.5929
P-glycoprotein substrateSubstrate0.8539
P-glycoprotein inhibitor IInhibitor0.655
P-glycoprotein inhibitor IINon-inhibitor0.9137
Renal organic cation transporterNon-inhibitor0.8464
CYP450 2C9 substrateNon-substrate0.5216
CYP450 2D6 substrateNon-substrate0.78
CYP450 3A4 substrateSubstrate0.5889
CYP450 1A2 substrateNon-inhibitor0.7758
CYP450 2C9 inhibitorNon-inhibitor0.6047
CYP450 2D6 inhibitorNon-inhibitor0.8967
CYP450 2C19 inhibitorNon-inhibitor0.6123
CYP450 3A4 inhibitorNon-inhibitor0.6943
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5844
Ames testNon AMES toxic0.6285
CarcinogenicityNon-carcinogens0.7229
BiodegradationNot ready biodegradable0.958
Rat acute toxicity2.5070 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.826
hERG inhibition (predictor II)Non-inhibitor0.5705
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 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 / Piperidines / Organosulfonamides / Benzenoids / Vinylogous amides / Tertiary alcohols / Sulfonyls / Secondary carboxylic acid amides / Secondary alcohols / Amino acids and derivatives
show 7 more
Substituents
Dihydroindole / Secondary aliphatic/aromatic amine / Piperidine / Organosulfonic acid amide / Benzenoid / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Sulfonyl / Tertiary alcohol / Vinylogous amide
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
N-acylpiperidine, hydroxypiperidine, biindole (CHEBI:45492)

Targets

Kind
Protein
Organism
Human
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. 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]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:15