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

Generic 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
DrugBank Accession Number
DB03737
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 385.3889
Monoisotopic: 385.143784348
Chemical Formula
C20H20FN3O4
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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
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
1,2-aminoalcohol / Alcohol / Alkyl aryl ether / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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][C@](C)(O)[C@]([H])(N)[C@]([H])(O)C#CC1=C(F)C=CC2=C1\C(=C\C1=C(OC)C=CN1)C(=O)N2

References

General References
Not Available
PubChem Compound
5288222
PubChem Substance
46505468
ChemSpider
4450427
BindingDB
10109
ChEMBL
CHEMBL354634
ZINC
ZINC000014947116
PDBe Ligand
FMD
PDB Entries
1r78

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
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
Polarizability39.17 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/MSsplash10-014r-0009000000-a1242cae8d661d4e97df
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00yi-2019000000-31c3e75ceb6a5493431b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gbi-1029000000-1e281155f181fc48442b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01b9-7019000000-ede1614f5f70262572e5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014l-4191000000-43b5a45d5993ce0d5009
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00li-2194000000-501219def131ef216964
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]-186.89459
predicted
DeepCCS 1.0 (2019)
[M+H]+189.0396
predicted
DeepCCS 1.0 (2019)
[M+Na]+194.95256
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  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. [Article]
  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. [Article]

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