You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
Name(4R)-7-chloro-9-methyl-1-oxo-1,2,4,9-tetrahydrospiro[beta-carboline-3,4'-piperidine]-4-carbonitrile
Accession NumberDB08166
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 328.796
Monoisotopic: 328.109088893
Chemical FormulaC17H17ClN4O
InChI KeyInChIKey=LPFQFJAOMCGYCP-GFCCVEGCSA-N
InChI
InChI=1S/C17H17ClN4O/c1-22-13-8-10(18)2-3-11(13)14-12(9-19)17(4-6-20-7-5-17)21-16(23)15(14)22/h2-3,8,12,20H,4-7H2,1H3,(H,21,23)/t12-/m1/s1
IUPAC Name
(4'R)-7'-chloro-9'-methyl-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=CC(Cl)=CC=C23)C(=O)NC11CCNCC1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as beta carbolines. These are compounds containing a 9H-pyrido[3,4-b]indole moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyridoindoles
Direct ParentBeta carbolines
Alternative Parents
Substituents
  • Beta-carboline
  • Indolecarboxylic acid derivative
  • Indole
  • Aralkylamine
  • Chlorobenzene
  • Benzenoid
  • Substituted pyrrole
  • Piperidine
  • N-methylpyrrole
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Pyrrole
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Secondary amine
  • Nitrile
  • Carbonitrile
  • Secondary aliphatic amine
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.992
Blood Brain Barrier+0.6275
Caco-2 permeable-0.5962
P-glycoprotein substrateSubstrate0.8467
P-glycoprotein inhibitor IInhibitor0.6624
P-glycoprotein inhibitor IIInhibitor0.5934
Renal organic cation transporterInhibitor0.5793
CYP450 2C9 substrateNon-substrate0.7611
CYP450 2D6 substrateNon-substrate0.7073
CYP450 3A4 substrateSubstrate0.7405
CYP450 1A2 substrateInhibitor0.6138
CYP450 2C9 inhibitorInhibitor0.5162
CYP450 2D6 inhibitorInhibitor0.5372
CYP450 2C19 inhibitorNon-inhibitor0.5608
CYP450 3A4 inhibitorInhibitor0.6339
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6885
Ames testNon AMES toxic0.638
CarcinogenicityNon-carcinogens0.9324
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7053 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9287
hERG inhibition (predictor II)Inhibitor0.8944
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.141 mg/mLALOGPS
logP1.32ALOGPS
logP0.78ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)11.84ChemAxon
pKa (Strongest Basic)9.93ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.85 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity89.12 m3·mol-1ChemAxon
Polarizability34.45 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

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 through: the regulation of MYC transcriptional activity, the regulation of cell cycle progression and by phosphorylation and inhibition of proapoptotic proteins (BAD, MAP3K5, FOXO3). Phosphorylation of MYC ...
Gene Name:
PIM1
Uniprot ID:
P11309
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 ]
Comments
comments powered by Disqus
Drug created on September 15, 2010 15:29 / Updated on September 16, 2013 18:08