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Identification
Name2,3-DIMETHOXY-12H-[1,3]DIOXOLO[5,6]INDENO[1,2-C]ISOQUINOLIN-6-IUM
Accession NumberDB07354
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: 322.3346
Monoisotopic: 322.107933005
Chemical FormulaC19H16NO4
InChI KeyInChIKey=LXDREMZQGAILJU-UHFFFAOYSA-O
InChI
InChI=1S/C19H15NO4/c1-21-15-5-11-8-20-19-13-7-18-17(23-9-24-18)4-10(13)3-14(19)12(11)6-16(15)22-2/h4-8H,3,9H2,1-2H3/p+1
IUPAC Name
15,16-dimethoxy-5,7-dioxa-20-azapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13,15,17,19-octaen-20-ium
SMILES
COC1=C(OC)C=C2C3=C([NH+]=CC2=C1)C1=C(C3)C=C2OCOC2=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoquinolines and derivatives
Sub ClassBenzylisoquinolines
Direct ParentBenzylisoquinolines
Alternative Parents
Substituents
  • Benzylisoquinoline
  • Benzodioxole
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Pyridinium
  • Pyridine
  • Heteroaromatic compound
  • Oxacycle
  • Azacycle
  • Ether
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic cation
  • 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+0.9016
Blood Brain Barrier+0.9384
Caco-2 permeable+0.5989
P-glycoprotein substrateNon-substrate0.6404
P-glycoprotein inhibitor INon-inhibitor0.908
P-glycoprotein inhibitor IINon-inhibitor0.9381
Renal organic cation transporterNon-inhibitor0.7671
CYP450 2C9 substrateNon-substrate0.8751
CYP450 2D6 substrateNon-substrate0.7502
CYP450 3A4 substrateSubstrate0.5818
CYP450 1A2 substrateInhibitor0.8958
CYP450 2C9 inhibitorInhibitor0.5061
CYP450 2D6 inhibitorInhibitor0.7106
CYP450 2C19 inhibitorInhibitor0.7497
CYP450 3A4 inhibitorInhibitor0.7661
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9207
Ames testAMES toxic0.7453
CarcinogenicityNon-carcinogens0.9724
BiodegradationReady biodegradable0.7729
Rat acute toxicity2.5745 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9714
hERG inhibition (predictor II)Non-inhibitor0.9325
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 Solubility0.00126 mg/mLALOGPS
logP0.56ALOGPS
logP3.2ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)11.52ChemAxon
pKa (Strongest Basic)5.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area51.06 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89 m3·mol-1ChemAxon
Polarizability35.29 Å3ChemAxon
Number of Rings5ChemAxon
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:
Poly(a) rna binding
Specific Function:
Releases the supercoiling and torsional tension of DNA introduced during the DNA replication and transcription by transiently cleaving and rejoining one strand of the DNA duplex. Introduces a single-strand break via transesterification at a target site in duplex DNA. The scissile phosphodiester is attacked by the catalytic tyrosine of the enzyme, resulting in the formation of a DNA-(3'-phosphot...
Gene Name:
TOP1
Uniprot ID:
P11387
Molecular Weight:
90725.19 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 15:20 / Updated on September 16, 2013 18:06