1S,3AS,8AS-TRIMETHYL-1-OXIDO-1,2,3,3A,8,8A-HEXAHYDROPYRROLO[2,3-B]INDOL-5-YL 2-ETHYLPHENYLCARBAMATE

Identification

Name
1S,3AS,8AS-TRIMETHYL-1-OXIDO-1,2,3,3A,8,8A-HEXAHYDROPYRROLO[2,3-B]INDOL-5-YL 2-ETHYLPHENYLCARBAMATE
Accession Number
DB07846
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: 381.4681
Monoisotopic: 381.205241745
Chemical Formula
C22H27N3O3
InChI Key
MVHRCJQCKYPDRL-UHFFFAOYSA-N
InChI
InChI=1S/C22H27N3O3/c1-5-15-8-6-7-9-18(15)23-21(26)28-16-10-11-19-17(14-16)22(2)12-13-25(4,27)20(22)24(19)3/h6-11,14,20H,5,12-13H2,1-4H3,(H,23,26)
IUPAC Name
1-({1,3a,8-trimethyl-1-oxo-1H,2H,3H,3aH,8H,8aH-1λ⁵-pyrrolo[2,3-b]indol-5-yl}oxy)-N-(2-ethylphenyl)methanimidic acid
SMILES
CCC1=CC=CC=C1N=C(O)OC1=CC2=C(C=C1)N(C)C1C2(C)CCN1(C)=O

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
74077203
PubChem Substance
99444317
HET
GSG
PDB Entries
2bag

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 Solubility0.00577 mg/mLALOGPS
logP2.34ALOGPS
logP4.81ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)7.48ChemAxon
pKa (Strongest Basic)0.42ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.94 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity112.4 m3·mol-1ChemAxon
Polarizability40.98 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9873
Blood Brain Barrier+0.9696
Caco-2 permeable-0.5492
P-glycoprotein substrateSubstrate0.7444
P-glycoprotein inhibitor INon-inhibitor0.537
P-glycoprotein inhibitor IINon-inhibitor0.5235
Renal organic cation transporterNon-inhibitor0.8348
CYP450 2C9 substrateNon-substrate0.7912
CYP450 2D6 substrateNon-substrate0.7786
CYP450 3A4 substrateSubstrate0.7352
CYP450 1A2 substrateNon-inhibitor0.7
CYP450 2C9 inhibitorNon-inhibitor0.7097
CYP450 2D6 inhibitorNon-inhibitor0.7186
CYP450 2C19 inhibitorNon-inhibitor0.6305
CYP450 3A4 inhibitorNon-inhibitor0.6526
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5312
Ames testNon AMES toxic0.6033
CarcinogenicityNon-carcinogens0.8482
BiodegradationNot ready biodegradable0.716
Rat acute toxicity3.0706 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8001
hERG inhibition (predictor II)Non-inhibitor0.6731
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not 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
Indoles / Dialkylarylamines / N-alkylpyrrolidines / Benzene and substituted derivatives / Trialkyl amine oxides / Pyrroles / Trisubstituted amine oxides and derivatives / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids and derivatives / Azacyclic compounds
show 5 more
Substituents
Pyrroloindole / Indole / Dialkylarylamine / Monocyclic benzene moiety / N-alkylpyrrolidine / Benzenoid / Trialkyl amine oxide / Pyrrole / Pyrrolidine / Azacycle
show 15 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. 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 15:26 / Updated on December 01, 2017 15:56