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Identification
Name8-bromo-4-(2-chlorophenyl)-N-(2-hydroxyethyl)-6-methyl-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-e]indole-7-carboxamide
Accession NumberDB08365
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 476.708
Monoisotopic: 474.993446337
Chemical FormulaC20H15BrClN3O4
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyrroloindoles
Direct ParentPyrroloindoles
Alternative Parents
Substituents
  • Pyrroloindole
  • Indolecarboxylic acid derivative
  • Indolecarboxamide derivative
  • Isoindolone
  • Isoindole or derivatives
  • Isoindoline
  • Indole
  • Pyrrole-2-carboxylic acid or derivatives
  • Pyrrole-2-carboxamide
  • N-acylethanolamine
  • Halobenzene
  • Dicarboximide
  • Chlorobenzene
  • Benzenoid
  • Substituted pyrrole
  • N-methylpyrrole
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Aryl bromide
  • Heteroaromatic compound
  • Vinylogous halide
  • Pyrrole
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Alkanolamine
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organobromide
  • Organohalogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot 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 phosphorylation of CDK1 on 'Tyr-15'. Specifically phosphorylates and inactivates cyclin B1-complexed CDK1 reaching a maximum during G2 phase and a minimum as cells enter M phase. Phosphorylation of cycl...
Gene Name:
WEE1
Uniprot ID:
P30291
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 ]
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Drug created on September 15, 2010 15:31 / Updated on September 16, 2013 18:09