(4ar,6s,8ar)-11-[8-(1,3-Dioxo-1,3-Dihydro-2h-Isoindol-2-Yl)Octyl]-6-Hydroxy-3-Methoxy-5,6,9,10-Tetrahydro-4ah-[1]Benzofuro[3a,3,2-Ef][2]Benzazepin-11-Ium

Identification

Name
(4ar,6s,8ar)-11-[8-(1,3-Dioxo-1,3-Dihydro-2h-Isoindol-2-Yl)Octyl]-6-Hydroxy-3-Methoxy-5,6,9,10-Tetrahydro-4ah-[1]Benzofuro[3a,3,2-Ef][2]Benzazepin-11-Ium
Accession Number
DB02673  (EXPT01601)
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: 529.6466
Monoisotopic: 529.270247304
Chemical Formula
C32H37N2O5
InChI Key
VLGAHTYYCHWLNI-BHRZLAGCSA-N
InChI
InChI=1S/C32H37N2O5/c1-38-26-13-12-22-21-33(19-16-32-15-14-23(35)20-27(32)39-29(26)28(22)32)17-8-4-2-3-5-9-18-34-30(36)24-10-6-7-11-25(24)31(34)37/h6-7,10-15,21,23,27,35H,2-5,8-9,16-20H2,1H3/q+1/t23-,27-,32-/m0/s1
IUPAC Name
[(1S,12S,14R)-4-[8-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)octyl]-14-hydroxy-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]heptadeca-5,7,10(17),15-tetraen-9-ylidene](methyl)oxidanium
SMILES
[H][[email protected]]12C[[email protected]@]([H])(O)C=C[[email protected]]11CCN(CCCCCCCCN3C(=O)C4=CC=CC=C4C3=O)C=C3C=CC(=[O+]C)C(O2)=C13

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAcetylcholinesteraseNot 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
5288394
PubChem Substance
46504838
ChemSpider
4450584
BindingDB
10406
ChEMBL
CHEMBL490866
HET
GL8
PDB Entries
1w4l

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 Solubility0.00831 mg/mLALOGPS
logP4.87ALOGPS
logP2.42ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)14.79ChemAxon
pKa (Strongest Basic)7.85ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area104.22 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity166.73 m3·mol-1ChemAxon
Polarizability60.38 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5658
Blood Brain Barrier+0.9679
Caco-2 permeable+0.5885
P-glycoprotein substrateSubstrate0.8713
P-glycoprotein inhibitor INon-inhibitor0.6756
P-glycoprotein inhibitor IINon-inhibitor0.5451
Renal organic cation transporterInhibitor0.5426
CYP450 2C9 substrateNon-substrate0.7111
CYP450 2D6 substrateNon-substrate0.6809
CYP450 3A4 substrateSubstrate0.7468
CYP450 1A2 substrateNon-inhibitor0.8954
CYP450 2C9 inhibitorNon-inhibitor0.7249
CYP450 2D6 inhibitorNon-inhibitor0.8765
CYP450 2C19 inhibitorNon-inhibitor0.7644
CYP450 3A4 inhibitorInhibitor0.8454
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9147
Ames testNon AMES toxic0.7209
CarcinogenicityNon-carcinogens0.8826
BiodegradationNot ready biodegradable0.9973
Rat acute toxicity2.7395 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9468
hERG inhibition (predictor II)Non-inhibitor0.5404
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 benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzazepines
Sub Class
Not Available
Direct Parent
Benzazepines
Alternative Parents
Phthalimides / Isoindoles / Coumarans / Anisoles / Azepines / Alkyl aryl ethers / N-substituted carboxylic acid imides / Secondary alcohols / Oxacyclic compounds / Azacyclic compounds
show 4 more
Substituents
Phthalimide / Benzazepine / Isoindolone / Coumaran / Isoindoline / Isoindole / Isoindole or derivatives / Anisole / Phenol ether / Alkyl aryl ether
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Serine hydrolase activity
Specific Function
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name
ACHE
Uniprot ID
P22303
Uniprot Name
Acetylcholinesterase
Molecular Weight
67795.525 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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:01