NAV

(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

Generic 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
DrugBank Accession Number
DB07604
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 336.3844
Monoisotopic: 336.147392516
Chemical Formula
C20H20N2O3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USarcoplasmic/endoplasmic reticulum calcium ATPase 1Not AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
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 / Alkanolamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Heteroaromatic compound / Hydrocarbon derivative / Isoindole or derivatives / Isoindoline
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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[9.6.1.0^{2,9}.0^{3,7}.0^{15,18}]octadeca-1(17),5,11(18),12,14-pentaen-4-one
SMILES
[H][C@@]12CC3=C4C(NC=C4[C@]1([H])[C@]1([H])N(C(O)=C(C(C)=O)C1=O)C2(C)C)=CC=C3

References

General References
Not Available
PubChem Compound
54682463
PubChem Substance
99444075
ChemSpider
58753
PDBe Ligand
CZA
PDB Entries
2eat / 2eau / 2o9j / 2oa0 / 3fgo / 3fpb / 3fps / 4bew / 4ycl / 5mpm

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
logP3.23Chemaxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.37Chemaxon
pKa (Strongest Basic)-1.8Chemaxon
Physiological Charge-1Chemaxon
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-MSsplash10-0fdk-2953000000-966a065ecec48e636984
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-79ef09cd9f1a3e717d52
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-e67dab114c16763b2a86
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0249000000-a9d254c5e7569456a078
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0049000000-1ea3a4bc4ca6225896b1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0101-2973000000-d35ec53d6cdfa0a4cdf9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-6494000000-76c12b1f0f4cb0a76506
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-191.2786
predicted
DeepCCS 1.0 (2019)
[M+H]+193.67415
predicted
DeepCCS 1.0 (2019)
[M+Na]+199.58667
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Sarcoplasmic/endoplasmic reticulum calcium ATPase 1
Kind
Protein
Organism
Humans
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. [Article]

Drug created at September 15, 2010 21:24 / Updated at June 12, 2020 16:52