4-((3r,4s,5r)-4-Amino-3,5-Dihydroxy-Hex-1-Ynyl)-5-Fluoro-3-[1-(3-Methoxy-1h-Pyrrol-2-Yl)-Meth-(Z)-Ylidene]-1,3-Dihydro-Indol-2-One

Identification

Name
4-((3r,4s,5r)-4-Amino-3,5-Dihydroxy-Hex-1-Ynyl)-5-Fluoro-3-[1-(3-Methoxy-1h-Pyrrol-2-Yl)-Meth-(Z)-Ylidene]-1,3-Dihydro-Indol-2-One
Accession Number
DB03737  (EXPT01454)
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: 385.3889
Monoisotopic: 385.143784348
Chemical Formula
C20H20FN3O4
InChI Key
RAKYKJWUUUKCCW-MPLBGYFPSA-N
InChI
InChI=1S/C20H20FN3O4/c1-10(25)19(22)16(26)6-3-11-13(21)4-5-14-18(11)12(20(27)24-14)9-15-17(28-2)7-8-23-15/h4-5,7-10,16,19,23,25-26H,22H2,1-2H3,(H,24,27)/b12-9-/t10-,16-,19+/m1/s1
IUPAC Name
(3Z)-4-[(3R,4S,5R)-4-amino-3,5-dihydroxyhex-1-yn-1-yl]-5-fluoro-3-[(3-methoxy-1H-pyrrol-2-yl)methylidene]-2,3-dihydro-1H-indol-2-one
SMILES
[H][[email protected]](C)(O)[[email protected]]([H])(N)[[email protected]]([H])(O)C#CC1=C(F)C=CC2=C1\C(=C\C1=C(OC)C=CN1)C(=O)N2

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
5288222
PubChem Substance
46505468
ChemSpider
4450427
BindingDB
10109
ChEMBL
CHEMBL354634
HET
FMD
PDB Entries
1r78

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 Solubility0.0201 mg/mLALOGPS
logP1.33ALOGPS
logP1.01ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)11.32ChemAxon
pKa (Strongest Basic)8.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area120.6 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity101.5 m3·mol-1ChemAxon
Polarizability39.02 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9137
Blood Brain Barrier-0.6405
Caco-2 permeable-0.5776
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.9477
P-glycoprotein inhibitor IINon-inhibitor0.978
Renal organic cation transporterNon-inhibitor0.9538
CYP450 2C9 substrateNon-substrate0.8925
CYP450 2D6 substrateNon-substrate0.8303
CYP450 3A4 substrateNon-substrate0.5114
CYP450 1A2 substrateInhibitor0.5943
CYP450 2C9 inhibitorNon-inhibitor0.673
CYP450 2D6 inhibitorNon-inhibitor0.8844
CYP450 2C19 inhibitorNon-inhibitor0.7187
CYP450 3A4 inhibitorNon-inhibitor0.785
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5649
Ames testNon AMES toxic0.5576
CarcinogenicityNon-carcinogens0.9047
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5951 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9906
hERG inhibition (predictor II)Non-inhibitor0.7186
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
Alkyl aryl ethers / Substituted pyrroles / Aryl fluorides / Benzenoids / Heteroaromatic compounds / Secondary carboxylic acid amides / Secondary alcohols / 1,2-aminoalcohols / Amino acids and derivatives / Lactams
show 7 more
Substituents
Dihydroindole / Alkyl aryl ether / Substituted pyrrole / Benzenoid / Aryl halide / Aryl fluoride / Pyrrole / Heteroaromatic compound / 1,2-aminoalcohol / Lactam
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Details
1. Cyclin-dependent kinase 2
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 15:18