NAV

(4R)-7,8-dichloro-1',9-dimethyl-1-oxo-1,2,4,9-tetrahydrospiro[beta-carboline-3,4'-piperidine]-4-carbonitrile

Identification

Generic Name
(4R)-7,8-dichloro-1',9-dimethyl-1-oxo-1,2,4,9-tetrahydrospiro[beta-carboline-3,4'-piperidine]-4-carbonitrile
DrugBank Accession Number
DB07242
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 377.268
Monoisotopic: 376.085766632
Chemical Formula
C18H18Cl2N4O
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDeath-associated protein kinase 3Not AvailableHumans
USerine/threonine-protein kinase pim-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 beta carbolines. These are compounds containing a 9H-pyrido[3,4-b]indole moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Pyridoindoles
Direct Parent
Beta carbolines
Alternative Parents
Indolecarboxylic acids and derivatives / 3-alkylindoles / N-alkylindoles / 2-heteroaryl carboxamides / Aralkylamines / Piperidines / Aryl chlorides / N-methylpyrroles / Benzenoids / Heteroaromatic compounds
show 11 more
Substituents
2-heteroaryl carboxamide / 3-alkylindole / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid
show 26 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
XGUIMGJMQKZRGM-LLVKDONJSA-N
InChI
InChI=1S/C18H18Cl2N4O/c1-23-7-5-18(6-8-23)11(9-21)13-10-3-4-12(19)14(20)15(10)24(2)16(13)17(25)22-18/h3-4,11H,5-8H2,1-2H3,(H,22,25)/t11-/m1/s1
IUPAC Name
(4'R)-7',8'-dichloro-1,9'-dimethyl-1'-oxo-1',2',4',9'-tetrahydrospiro[piperidine-4,3'-pyrido[3,4-b]indole]-4'-carbonitrile
SMILES
[H][C@@]1(C#N)C2=C(N(C)C3=C(Cl)C(Cl)=CC=C23)C(=O)NC11CCN(C)CC1

References

General References
Not Available
PubChem Compound
24851688
PubChem Substance
99443713
ChemSpider
25056752
ZINC
ZINC000024963803
PDBe Ligand
7CP
PDB Entries
3bhy / 3cxw

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 Solubility0.107 mg/mLALOGPS
logP3.06ALOGPS
logP1.93Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)12.87Chemaxon
pKa (Strongest Basic)8.34Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area61.06 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity99.22 m3·mol-1Chemaxon
Polarizability38.62 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.7577
Caco-2 permeable+0.566
P-glycoprotein substrateSubstrate0.8335
P-glycoprotein inhibitor IInhibitor0.7015
P-glycoprotein inhibitor IIInhibitor0.5705
Renal organic cation transporterInhibitor0.5568
CYP450 2C9 substrateNon-substrate0.8246
CYP450 2D6 substrateNon-substrate0.7195
CYP450 3A4 substrateSubstrate0.8256
CYP450 1A2 substrateNon-inhibitor0.598
CYP450 2C9 inhibitorNon-inhibitor0.6322
CYP450 2D6 inhibitorNon-inhibitor0.7715
CYP450 2C19 inhibitorNon-inhibitor0.6004
CYP450 3A4 inhibitorInhibitor0.752
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6931
Ames testNon AMES toxic0.6447
CarcinogenicityNon-carcinogens0.933
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7667 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9403
hERG inhibition (predictor II)Inhibitor0.6848
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 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

Targets

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Details1. Death-associated protein kinase 3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Rho gtpase binding
Specific Function
Serine/threonine kinase which is involved in the regulation of apoptosis, autophagy, transcription, translation and actin cytoskeleton reorganization. Involved in the regulation of smooth muscle co...
Gene Name
DAPK3
Uniprot ID
O43293
Uniprot Name
Death-associated protein kinase 3
Molecular Weight
52535.165 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]
Details2. Serine/threonine-protein kinase pim-1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcription factor binding
Specific Function
Proto-oncogene with serine/threonine kinase activity involved in cell survival and cell proliferation and thus providing a selective advantage in tumorigenesis. Exerts its oncogenic activity throug...
Gene Name
PIM1
Uniprot ID
P11309
Uniprot Name
Serine/threonine-protein kinase pim-1
Molecular Weight
45411.905 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 21:19 / Updated at June 12, 2020 16:52