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Identification
Name(4R)-7,8-dichloro-1',9-dimethyl-1-oxo-1,2,4,9-tetrahydrospiro[beta-carboline-3,4'-piperidine]-4-carbonitrile
Accession NumberDB07242
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: 377.268
Monoisotopic: 376.085766632
Chemical FormulaC18H18Cl2N4O
InChI KeyInChIKey=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
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
  • 1,2-dichlorobenzene
  • Aralkylamine
  • Chlorobenzene
  • Benzenoid
  • Substituted pyrrole
  • Piperidine
  • N-methylpyrrole
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Nitrile
  • Carbonitrile
  • 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+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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.107 mg/mLALOGPS
logP3.06ALOGPS
logP1.93ChemAxon
logS-3.5ALOGPS
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 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:
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 contraction. Regulates both type I (caspase-dependent) apoptotic and type II (caspase-independent) autophagic cell deaths signal, depending on the cellular setting. Involved in regulation of starvation-...
Gene Name:
DAPK3
Uniprot ID:
O43293
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 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 ]
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Drug created on September 15, 2010 15:19 / Updated on September 16, 2013 18:05