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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
SaltsNot Available
Brand namesNot Available
Brand mixturesNot 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-]
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassIndoles and Derivatives
SubclassPyrroloindoles
Direct parentPyrroloindoles
Alternative parentsPhenylcarbamates; Phenethylamines; Indoles; Phenol Ethers; Pyrrolidines; Pyrroles; Tertiary Amines; Carbamic Acids and Derivatives; Polyamines; Ethers; Aminals; Amine Oxides and Derivatives
Substituentsphenylcarbamate; indole; phenethylamine; phenol ether; benzene; pyrrolidine; pyrrole; carbamic acid derivative; tertiary amine; ether; aminal; polyamine; amine; n-oxide; organonitrogen compound
Classification descriptionThis compound belongs to the pyrroloindoles. These are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
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
Property Value Probability
Human Intestinal Absorption + 0.9873
Blood Brain Barrier + 0.9696
Caco-2 permeable - 0.5492
P-glycoprotein substrate Substrate 0.7444
P-glycoprotein inhibitor I Non-inhibitor 0.537
P-glycoprotein inhibitor II Non-inhibitor 0.5235
Renal organic cation transporter Non-inhibitor 0.8348
CYP450 2C9 substrate Non-substrate 0.7912
CYP450 2D6 substrate Non-substrate 0.7786
CYP450 3A4 substrate Substrate 0.7352
CYP450 1A2 substrate Non-inhibitor 0.7
CYP450 2C9 substrate Non-inhibitor 0.7097
CYP450 2D6 substrate Non-inhibitor 0.7186
CYP450 2C19 substrate Non-inhibitor 0.6305
CYP450 3A4 substrate Non-inhibitor 0.6526
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5312
Ames test Non AMES toxic 0.6033
Carcinogenicity Non-carcinogens 0.8482
Biodegradation Not ready biodegradable 0.716
Rat acute toxicity 3.0706 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8001
hERG inhibition (predictor II) Non-inhibitor 0.6731
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00908ALOGPS
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound46937098
PubChem Substance99444317
HETGSG
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

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