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Identification
Name1S,3AS,8AS-TRIMETHYL-1-OXIDO-1,2,3,3A,8,8A-HEXAHYDROPYRROLO[2,3-B]INDOL-5-YL 2-ETHYLPHENYLCARBAMATE
Accession NumberDB07846
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS numberNot Available
WeightAverage: 381.4681
Monoisotopic: 381.205241745
Chemical FormulaC22H27N3O3
InChI KeyMVHRCJQCKYPDRL-HOKHCIIBSA-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)/t20-,22+,25-/m0/s1
IUPAC Name
(1S,3aR,8aS)-5-{[(2-ethylphenyl)carbamoyl]oxy}-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-1-ium-1-olate
SMILES
[H][C@@]12N(C)C3=CC=C(OC(=O)NC4=CC=CC=C4CC)C=C3[C@@]1(C)CC[N@+]2(C)[O-]
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
  • Phenylcarbamate
  • Indole
  • Dialkylarylamine
  • Benzenoid
  • N-alkylpyrrolidine
  • Monocyclic benzene moiety
  • Pyrrolidine
  • Pyrrole
  • Tertiary amine
  • Azacycle
  • Trisubstituted n-oxide
  • Monocarboxylic acid or derivatives
  • N-oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
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+0.9873
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 substrateNon-inhibitor0.7097
CYP450 2D6 substrateNon-inhibitor0.7186
CYP450 2C19 substrateNon-inhibitor0.6305
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00908 mg/mLALOGPS
logP2.42ALOGPS
logP4.08ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)12.9ChemAxon
pKa (Strongest Basic)0.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area68.45 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity111.64 m3·mol-1ChemAxon
Polarizability42.36 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 ReferenceNot 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

1. Acetylcholinesterase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Acetylcholinesterase P22303 Details

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

Comments
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Drug created on September 15, 2010 15:26 / Updated on September 16, 2013 18:07