Propidium

Identification

Name
Propidium
Accession Number
DB02166  (EXPT02661)
Type
Small Molecule
Groups
Experimental
Description

Quaternary ammonium analog of ethidium; an intercalating dye with a specific affinity to certain forms of DNA and, used as diiodide, to separate them in density gradients; also forms fluorescent complexes with cholinesterase which it inhibits. [PubChem]

Structure
Thumb
Synonyms
Not Available
Categories
UNII
74NX23J96Y
CAS number
36015-30-2
Weight
Average: 414.5857
Monoisotopic: 414.278347108
Chemical Formula
C27H34N4
InChI Key
ZDWVWKDAWBGPDN-UHFFFAOYSA-O
InChI
InChI=1S/C27H33N4/c1-4-31(3,5-2)17-9-16-30-26-19-22(29)13-15-24(26)23-14-12-21(28)18-25(23)27(30)20-10-7-6-8-11-20/h6-8,10-15,18-19,29H,4-5,9,16-17,28H2,1-3H3/q+1/p+1
IUPAC Name
3,8-diamino-5-{3-[diethyl(methyl)azaniumyl]propyl}-6-phenylphenanthridin-5-ium
SMILES
CC[N+](C)(CC)CCC[N+]1=C(C2=CC=CC=C2)C2=C(C=CC(N)=C2)C2=C1C=C(N)C=C2

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAcetylcholinesteraseNot 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
4939
PubChem Substance
46506410
ChemSpider
4770
BindingDB
31904
ChEBI
51246
ChEMBL
CHEMBL332935
HET
PRM
PDB Entries
1n5r / 6esj

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 Solubility7.13e-07 mg/mLALOGPS
logP1.56ALOGPS
logP-4.6ChemAxon
logS-8.8ALOGPS
pKa (Strongest Basic)3.48ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.92 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity145.54 m3·mol-1ChemAxon
Polarizability49.6 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7303
Blood Brain Barrier+0.927
Caco-2 permeable+0.5616
P-glycoprotein substrateSubstrate0.798
P-glycoprotein inhibitor INon-inhibitor0.8231
P-glycoprotein inhibitor IIInhibitor0.7992
Renal organic cation transporterInhibitor0.5307
CYP450 2C9 substrateNon-substrate0.8738
CYP450 2D6 substrateNon-substrate0.5942
CYP450 3A4 substrateSubstrate0.5784
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.8787
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorInhibitor0.7701
CYP450 3A4 inhibitorNon-inhibitor0.5381
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6237
Ames testNon AMES toxic0.6243
CarcinogenicityNon-carcinogens0.8437
BiodegradationNot ready biodegradable0.9833
Rat acute toxicity2.7590 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9153
hERG inhibition (predictor II)Inhibitor0.9367
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Phenylquinolines
Direct Parent
Phenylquinolines
Alternative Parents
Phenanthridines and derivatives / Phenylpyridines / Aminoquinolines and derivatives / Isoquinolines and derivatives / Pyridinium derivatives / Benzene and substituted derivatives / Tetraalkylammonium salts / Heteroaromatic compounds / Azacyclic compounds / Primary amines
show 4 more
Substituents
Phenylquinoline / Benzoquinoline / Phenanthridine / 2-phenylpyridine / Aminoquinoline / Isoquinoline / Monocyclic benzene moiety / Pyridine / Pyridinium / Benzenoid
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
quaternary ammonium ion, phenanthridines (CHEBI:51246)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Serine hydrolase activity
Specific Function
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name
ACHE
Uniprot ID
P22303
Uniprot Name
Acetylcholinesterase
Molecular Weight
67795.525 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]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 14:54