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

Identification

Name
(4R)-7,8-dichloro-1',9-dimethyl-1-oxo-1,2,4,9-tetrahydrospiro[beta-carboline-3,4'-piperidine]-4-carbonitrile
Accession Number
DB07242
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: 377.268
Monoisotopic: 376.085766632
Chemical Formula
C18H18Cl2N4O
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][[email protected]@]1(C#N)C2=C(N(C)C3=C(Cl)C(Cl)=CC=C23)C(=O)NC11CCN(C)CC1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDeath-associated protein kinase 3Not AvailableHuman
USerine/threonine-protein kinase pim-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
24851688
PubChem Substance
99443713
ChemSpider
25056752
HET
7CP
PDB Entries
3bhy / 3cxw

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 Solubility0.107 mg/mLALOGPS
logP3.06ALOGPS
logP1.93ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)11.74ChemAxon
pKa (Strongest Basic)8.35ChemAxon
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

Taxonomy

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
Beta-carboline / Indolecarboxylic acid derivative / 3-alkylindole / N-alkylindole / Indole / 2-heteroaryl carboxamide / Aralkylamine / Aryl chloride / Aryl halide / N-methylpyrrole
show 26 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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. [PubMed:10592235]
Kind
Protein
Organism
Human
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. [PubMed:10592235]

Drug created on September 15, 2010 15:19 / Updated on December 01, 2017 15:48