8-bromo-4-(2-chlorophenyl)-N-(2-hydroxyethyl)-6-methyl-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-e]indole-7-carboxamide

Identification

Name
8-bromo-4-(2-chlorophenyl)-N-(2-hydroxyethyl)-6-methyl-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-e]indole-7-carboxamide
Accession Number
DB08365
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: 476.708
Monoisotopic: 474.993446337
Chemical Formula
C20H15BrClN3O4
InChI Key
XUAHLMVOYLUYSB-UHFFFAOYSA-N
InChI
InChI=1S/C20H15BrClN3O4/c1-25-12-8-10(9-4-2-3-5-11(9)22)13-15(19(28)24-18(13)27)14(12)16(21)17(25)20(29)23-6-7-26/h2-5,8,26H,6-7H2,1H3,(H,23,29)(H,24,27,28)
IUPAC Name
8-bromo-4-(2-chlorophenyl)-N-(2-hydroxyethyl)-6-methyl-1,3-dioxo-1H,2H,3H,6H-pyrrolo[3,4-e]indole-7-carboxamide
SMILES
CN1C2=C(C(Br)=C1C(=O)NCCO)C1=C(C(=O)NC1=O)C(=C2)C1=C(Cl)C=CC=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UWee1-like protein kinaseNot 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
11691442
PubChem Substance
99444836
ChemSpider
9866169
HET
P91
PDB Entries
3cqe

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 Solubility0.00731 mg/mLALOGPS
logP3.13ALOGPS
logP2.34ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)8.01ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.43 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity113.01 m3·mol-1ChemAxon
Polarizability43.89 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.982
Blood Brain Barrier-0.6795
Caco-2 permeable-0.6611
P-glycoprotein substrateSubstrate0.7333
P-glycoprotein inhibitor INon-inhibitor0.9732
P-glycoprotein inhibitor IINon-inhibitor0.9129
Renal organic cation transporterNon-inhibitor0.7669
CYP450 2C9 substrateNon-substrate0.768
CYP450 2D6 substrateNon-substrate0.8269
CYP450 3A4 substrateSubstrate0.5226
CYP450 1A2 substrateNon-inhibitor0.6477
CYP450 2C9 inhibitorNon-inhibitor0.5377
CYP450 2D6 inhibitorNon-inhibitor0.869
CYP450 2C19 inhibitorNon-inhibitor0.7797
CYP450 3A4 inhibitorInhibitor0.6519
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6686
Ames testNon AMES toxic0.7773
CarcinogenicityNon-carcinogens0.7845
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4752 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9386
hERG inhibition (predictor II)Inhibitor0.6513
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 pyrroloindoles. These are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting 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
Pyrroloindoles
Direct Parent
Pyrroloindoles
Alternative Parents
Indolecarboxamides and derivatives / Phthalimides / N-alkylindoles / Indoles / 2-heteroaryl carboxamides / Pyrrole carboxamides / N-acylethanolamines / Chlorobenzenes / Aryl bromides / Aryl chlorides
show 12 more
Substituents
Indolecarboxamide derivative / Indolecarboxylic acid derivative / Pyrroloindole / Phthalimide / N-alkylindole / Isoindolone / Indole / Isoindoline / Isoindole or derivatives / 2-heteroaryl carboxamide
show 35 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein tyrosine kinase activity
Specific Function
Acts as a negative regulator of entry into mitosis (G2 to M transition) by protecting the nucleus from cytoplasmically activated cyclin B1-complexed CDK1 before the onset of mitosis by mediating ph...
Gene Name
WEE1
Uniprot ID
P30291
Uniprot Name
Wee1-like protein kinase
Molecular Weight
71596.655 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]

Drug created on September 15, 2010 15:31 / Updated on December 01, 2017 16:03