Identification

Name
Alsterpaullone
Accession Number
DB04014  (EXPT00590)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 293.2768
Monoisotopic: 293.080041233
Chemical Formula
C16H11N3O3
InChI Key
OLUKILHGKRVDCT-UHFFFAOYSA-N
InChI
InChI=1S/C16H11N3O3/c20-15-8-12-11-7-9(19(21)22)5-6-14(11)18-16(12)10-3-1-2-4-13(10)17-15/h1-7,18H,8H2,(H,17,20)
IUPAC Name
14-nitro-8,18-diazatetracyclo[9.7.0.0²,⁷.0¹²,¹⁷]octadeca-1(11),2(7),3,5,12(17),13,15-heptaen-9-one
SMILES
[O-][N+](=O)C1=CC2=C(NC3=C2CC(=O)NC2=C3C=CC=C2)C=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlycogen synthase kinase-3 betaNot AvailableHuman
UCyclin-dependent kinase 5Not AvailableHuman
UCyclin-dependent kinase 1
inhibitor
Human
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
5005498
PubChem Substance
46504736
ChemSpider
4185120
BindingDB
84528
ChEBI
138488
ChEMBL
CHEMBL50894
Therapeutic Targets Database
DNC000188
HET
ATU
PDB Entries
1q3w

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 Solubility0.0237 mg/mLALOGPS
logP3.07ALOGPS
logP2.68ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area90.71 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity83.01 m3·mol-1ChemAxon
Polarizability29.68 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9809
Blood Brain Barrier+0.9749
Caco-2 permeable-0.5713
P-glycoprotein substrateNon-substrate0.6102
P-glycoprotein inhibitor INon-inhibitor0.8446
P-glycoprotein inhibitor IINon-inhibitor0.91
Renal organic cation transporterNon-inhibitor0.8442
CYP450 2C9 substrateNon-substrate0.7327
CYP450 2D6 substrateNon-substrate0.8348
CYP450 3A4 substrateSubstrate0.6117
CYP450 1A2 substrateInhibitor0.6909
CYP450 2C9 inhibitorNon-inhibitor0.7408
CYP450 2D6 inhibitorNon-inhibitor0.7548
CYP450 2C19 inhibitorNon-inhibitor0.5922
CYP450 3A4 inhibitorInhibitor0.8826
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6804
Ames testAMES toxic0.622
CarcinogenicityNon-carcinogens0.8178
BiodegradationNot ready biodegradable0.9851
Rat acute toxicity2.4368 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9892
hERG inhibition (predictor II)Non-inhibitor0.7521
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-MSNot Available
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 benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzazepines
Sub Class
Not Available
Direct Parent
Benzazepines
Alternative Parents
3-alkylindoles / Nitroaromatic compounds / Azepines / Benzenoids / Pyrroles / Heteroaromatic compounds / Secondary carboxylic acid amides / Lactams / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds
show 6 more
Substituents
Benzazepine / 3-alkylindole / Indole / Indole or derivatives / Nitroaromatic compound / Azepine / Benzenoid / Pyrrole / Heteroaromatic compound / Carboxamide group
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquitin protein ligase binding
Specific Function
Constitutively active protein kinase that acts as a negative regulator in the hormonal control of glucose homeostasis, Wnt signaling and regulation of transcription factors and microtubules, by pho...
Gene Name
GSK3B
Uniprot ID
P49841
Uniprot Name
Glycogen synthase kinase-3 beta
Molecular Weight
46743.865 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. 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]
Details
2. Cyclin-dependent kinase 5
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Tau-protein kinase activity
Specific Function
Proline-directed serine/threonine-protein kinase essential for neuronal cell cycle arrest and differentiation and may be involved in apoptotic cell death in neuronal diseases by triggering abortive...
Gene Name
CDK5
Uniprot ID
Q00535
Uniprot Name
Cyclin-dependent-like kinase 5
Molecular Weight
33304.125 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Details
3. Cyclin-dependent kinase 1
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Rna polymerase ii carboxy-terminal domain kinase activity
Specific Function
Plays a key role in the control of the eukaryotic cell cycle by modulating the centrosome cycle as well as mitotic onset; promotes G2-M transition, and regulates G1 progress and G1-S transition via...
Gene Name
CDK1
Uniprot ID
P06493
Uniprot Name
Cyclin-dependent kinase 1
Molecular Weight
34095.14 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:22