(6AR,11AS,11BR)-10-ACETYL-9-HYDROXY-7,7-DIMETHYL-2,6,6A,7,11A,11B-HEXAHYDRO-11H-PYRROLO[1',2':2,3]ISOINDOLO[4,5,6-CD]INDOL-11-ONE

Identification

Name
(6AR,11AS,11BR)-10-ACETYL-9-HYDROXY-7,7-DIMETHYL-2,6,6A,7,11A,11B-HEXAHYDRO-11H-PYRROLO[1',2':2,3]ISOINDOLO[4,5,6-CD]INDOL-11-ONE
Accession Number
DB07604
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: 336.3844
Monoisotopic: 336.147392516
Chemical Formula
C20H20N2O3
InChI Key
RLOAZVAJNNPPDI-DQYPLSBCSA-N
InChI
InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,25H,7H2,1-3H3/t12-,16+,17+/m1/s1
IUPAC Name
(2R,3S,9R)-5-acetyl-6-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),5,11(18),12,14-pentaen-4-one
SMILES
[H][[email protected]@]12CC3=C4C(NC=C4[[email protected]]1([H])[[email protected]]1([H])N(C(O)=C(C(C)=O)C1=O)C2(C)C)=CC=C3

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USarcoplasmic/endoplasmic reticulum calcium ATPase 1Not 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
54682463
PubChem Substance
99444075
ChemSpider
58753
HET
CZA
PDB Entries
2eat / 2eau / 2o9j / 2oa0 / 3fgo / 3fpb / 3fps / 4bew / 4ycl

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 Solubility0.169 mg/mLALOGPS
logP2.47ALOGPS
logP3.08ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.56ChemAxon
pKa (Strongest Basic)2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area73.4 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity104 m3·mol-1ChemAxon
Polarizability36.18 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9969
Blood Brain Barrier-0.8148
Caco-2 permeable-0.5701
P-glycoprotein substrateSubstrate0.6655
P-glycoprotein inhibitor INon-inhibitor0.5146
P-glycoprotein inhibitor IIInhibitor0.5886
Renal organic cation transporterNon-inhibitor0.886
CYP450 2C9 substrateNon-substrate0.6963
CYP450 2D6 substrateNon-substrate0.8243
CYP450 3A4 substrateSubstrate0.6359
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.8948
CYP450 2D6 inhibitorNon-inhibitor0.8507
CYP450 2C19 inhibitorNon-inhibitor0.545
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8241
Ames testAMES toxic0.8248
CarcinogenicityNon-carcinogens0.8408
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.6118 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9941
hERG inhibition (predictor II)Non-inhibitor0.8769
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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 3-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indoles
Direct Parent
3-alkylindoles
Alternative Parents
Isoindolines / Pyrrolizines / Benzenoids / Vinylogous amides / Vinylogous acids / Pyrrolines / Pyrrolidines / Pyrroles / Heteroaromatic compounds / Ketones
show 6 more
Substituents
3-alkylindole / Isoindoline / Isoindole or derivatives / Pyrrolizine / Benzenoid / Pyrrole / Pyrrolidine / Pyrroline / Vinylogous acid / Vinylogous amide
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Key regulator of striated muscle performance by acting as the major Ca(2+) ATPase responsible for the reuptake of cytosolic Ca(2+) into the sarcoplasmic reticulum. Catalyzes the hydrolysis of ATP c...
Gene Name
ATP2A1
Uniprot ID
O14983
Uniprot Name
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1
Molecular Weight
110251.36 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 15:24 / Updated on December 01, 2017 15:53