NAV

1-METHYL-5-(2-PHENOXYMETHYL-PYRROLIDINE-1-SULFONYL)-1H-INDOLE-2,3-DIONE

Identification

Generic Name
1-METHYL-5-(2-PHENOXYMETHYL-PYRROLIDINE-1-SULFONYL)-1H-INDOLE-2,3-DIONE
DrugBank Accession Number
DB08213
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 400.448
Monoisotopic: 400.10929245
Chemical Formula
C20H20N2O5S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCaspase-3Not 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 indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Not Available
Direct Parent
Indoles and derivatives
Alternative Parents
Phenoxy compounds / Phenol ethers / Aryl ketones / Alkyl aryl ethers / Organosulfonamides / Vinylogous amides / Tertiary carboxylic acid amides / Sulfonyls / Pyrrolidines / Lactams
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Substituents
Alkyl aryl ether / Aromatic heteropolycyclic compound / Aryl ketone / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Ether / Hydrocarbon derivative
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
sulfonamide (CHEBI:44274)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
PFAYCUAUBOGVDX-AWEZNQCLSA-N
InChI
InChI=1S/C20H20N2O5S/c1-21-18-10-9-16(12-17(18)19(23)20(21)24)28(25,26)22-11-5-6-14(22)13-27-15-7-3-2-4-8-15/h2-4,7-10,12,14H,5-6,11,13H2,1H3/t14-/m0/s1
IUPAC Name
1-methyl-5-{[(2S)-2-(phenoxymethyl)pyrrolidin-1-yl]sulfonyl}-2,3-dihydro-1H-indole-2,3-dione
SMILES
[H][C@@]1(COC2=CC=CC=C2)CCCN1S(=O)(=O)C1=CC2=C(C=C1)N(C)C(=O)C2=O

References

General References
Not Available
PubChem Compound
5288850
PubChem Substance
99444684
ChemSpider
4450922
BindingDB
10320
ChEMBL
CHEMBL293034
ZINC
ZINC000003870526
PDBe Ligand
MSI
PDB Entries
1gfw

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 Solubility0.0535 mg/mLALOGPS
logP1.89ALOGPS
logP1.98Chemaxon
logS-3.9ALOGPS
pKa (Strongest Basic)-4.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area83.99 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity103.31 m3·mol-1Chemaxon
Polarizability39.4 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9964
Blood Brain Barrier+0.8889
Caco-2 permeable-0.6298
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor IInhibitor0.6505
P-glycoprotein inhibitor IIInhibitor0.9391
Renal organic cation transporterNon-inhibitor0.5607
CYP450 2C9 substrateNon-substrate0.5977
CYP450 2D6 substrateNon-substrate0.7414
CYP450 3A4 substrateSubstrate0.6373
CYP450 1A2 substrateNon-inhibitor0.6922
CYP450 2C9 inhibitorInhibitor0.8763
CYP450 2D6 inhibitorNon-inhibitor0.878
CYP450 2C19 inhibitorInhibitor0.8451
CYP450 3A4 inhibitorInhibitor0.8792
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7521
Ames testNon AMES toxic0.5906
CarcinogenicityNon-carcinogens0.7355
BiodegradationNot ready biodegradable0.9612
Rat acute toxicity2.4657 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8868
hERG inhibition (predictor II)Inhibitor0.6824
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/MSsplash10-0pb9-0039400000-72026af909df2267fd68
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0039000000-28dcc1ea535864abb1dd
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zmi-4709300000-5e71cbc851ac886fead1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0019000000-2dcda96cabf004a56114
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4m-0039000000-be682856fadf8167a88b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-5941000000-10f3f5562238b86eedc6
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]-184.53972
predicted
DeepCCS 1.0 (2019)
[M+H]+186.89772
predicted
DeepCCS 1.0 (2019)
[M+Na]+193.35693
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Caspase-3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Phospholipase a2 activator activity
Specific Function
Involved in the activation cascade of caspases responsible for apoptosis execution. At the onset of apoptosis it proteolytically cleaves poly(ADP-ribose) polymerase (PARP) at a '216-Asp-|-Gly-217' ...
Gene Name
CASP3
Uniprot ID
P42574
Uniprot Name
Caspase-3
Molecular Weight
31607.58 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 21:29 / Updated at June 12, 2020 16:52