1,10-Phenanthroline

Identification

Name
1,10-Phenanthroline
Accession Number
DB02365  (EXPT02592)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • O-Phenanthroline
External IDs
NSC-203545 / NSC-4265
Categories
UNII
W4X6ZO7939
CAS number
66-71-7
Weight
Average: 180.2053
Monoisotopic: 180.068748266
Chemical Formula
C12H8N2
InChI Key
DGEZNRSVGBDHLK-UHFFFAOYSA-N
InChI
InChI=1S/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H
IUPAC Name
1,10-phenanthroline
SMILES
C1=CC2=CC=C3C=CC=NC3=C2N=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UMethyl-accepting chemotaxis protein IINot AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
UMetallo-beta-lactamase L1Not AvailablePseudomonas maltophilia
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
DrugInteraction
Acebutolol1,10-Phenanthroline may increase the bradycardic activities of Acebutolol.
AcetylcholineThe risk or severity of adverse effects can be increased when 1,10-Phenanthroline is combined with Acetylcholine.
AclidiniumThe therapeutic efficacy of Aclidinium can be decreased when used in combination with 1,10-Phenanthroline.
AgmatineThe therapeutic efficacy of Agmatine can be decreased when used in combination with 1,10-Phenanthroline.
AlcuroniumThe therapeutic efficacy of Alcuronium can be decreased when used in combination with 1,10-Phenanthroline.
AldosteroneThe therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Aldosterone.
Alprenolol1,10-Phenanthroline may increase the bradycardic activities of Alprenolol.
AmifampridineThe risk or severity of adverse effects can be increased when 1,10-Phenanthroline is combined with Amifampridine.
AmikacinThe therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Amikacin.
AmitriptylineThe therapeutic efficacy of Amitriptyline can be decreased when used in combination with 1,10-Phenanthroline.
Food Interactions
Not Available

References

Synthesis Reference

Judith N. Burstyn, Omar Green, Bhavesh A. Gandhi, "BIS(2,9-DI-TERT-BUTYL-1,10-PHENANTHROLINE)COPPER(I) COMPLEXES, METHODS OF SYNTHESIS, AND USES THEROF." U.S. Patent US20080206890, issued August 28, 2008.

US20080206890
General References
Not Available
External Links
KEGG Compound
C00604
PubChem Compound
1318
PubChem Substance
46505260
ChemSpider
1278
BindingDB
50092158
ChEBI
44975
ChEMBL
CHEMBL415879
HET
PHN
PDB Entries
1lih / 2fu7 / 2lig / 5tso / 5vj5

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
PropertyValueSource
melting point (°C)117 °CPhysProp
boiling point (°C)> 300 °CPhysProp
water solubility2690 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.78HANSCH,C ET AL. (1995)
pKa4.27 (at 20 °C)ALBERT,A ET AL. (1948)
Predicted Properties
PropertyValueSource
Water Solubility0.132 mg/mLALOGPS
logP2.31ALOGPS
logP2.29ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.78 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity53.9 m3·mol-1ChemAxon
Polarizability19.26 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9879
Blood Brain Barrier+0.9825
Caco-2 permeable-0.5136
P-glycoprotein substrateNon-substrate0.6487
P-glycoprotein inhibitor INon-inhibitor0.8831
P-glycoprotein inhibitor IINon-inhibitor0.9805
Renal organic cation transporterNon-inhibitor0.7775
CYP450 2C9 substrateNon-substrate0.866
CYP450 2D6 substrateNon-substrate0.8486
CYP450 3A4 substrateNon-substrate0.7961
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6111
Ames testAMES toxic0.8512
CarcinogenicityNon-carcinogens0.9476
BiodegradationNot ready biodegradable0.9838
Rat acute toxicity2.1323 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9681
hERG inhibition (predictor II)Non-inhibitor0.8708
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
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0fai-1900000000-8bf54d7a505254cd0f42
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-003r-1900000000-bf66a4d49c83dd24535e
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-003r-4900000000-e878f31ffa5b4af39dfd
Mass Spectrum (Electron Ionization)MSsplash10-001i-1900000000-e3edab983e41e183110a
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
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0900000000-7bdef677e6a80f05aa75
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0900000000-555e8d3f751a47049c5a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0900000000-c48df88a05c1dbab0adc
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0900000000-07ee18512e76f5b25dd1
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0fb9-0900000000-7a08b5b37861250df6bd
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0900000000-94a0600a96f48f8aa145
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0fc0-0900000000-0f2b71fb75d6e9f09b6c
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-29a83efe3a4c61b6e760
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-f6eedb340d4cf4ab269f
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-b8ee2e5a776aecb532ca
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-88682d0eaadc3985ae6f
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-5c3af3894358cf9d55fc
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-29a83efe3a4c61b6e760
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-e7952d19ca3578ac4501
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-e7952d19ca3578ac4501
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-62142b81fd0b92ba0c9d
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-9cbaa490715b11601fdc
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-7095641d365002c9b143
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-0f89-0900000000-c2a7113134a8fdaed496
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-0fb9-0900000000-b0fd72c65f3813200a20
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-004i-2900000000-4ffad714811e85731892
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-e090efe0cddbe7929cb2
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-4fc72504435ed95451ac
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-ea4fdf798419a11217f2
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-e090efe0cddbe7929cb2
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-e090efe0cddbe7929cb2
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-45485816bda8e7909167
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-faad3e6b74ee6ca53b6e
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-95bc3cc9f850ef71dcf8
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0f89-0900000000-7898242f42f1312b948e
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0fb9-0900000000-b850980e5765d03a2799
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-004i-2900000000-7ef9fd08d9b8abdebd80
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-2900000000-173c7b28196041ae8de1
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenanthrolines. These are aromatic polycyclic compounds containing the phenanthroline skeleton, which is a derivative of phenanthrene, and consists of two pyridine rings non-linearly joined by a benzene ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Phenanthrolines
Sub Class
Not Available
Direct Parent
Phenanthrolines
Alternative Parents
Quinolines and derivatives / Pyridines and derivatives / Benzenoids / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
1,10-phenanthroline / Quinoline / Benzenoid / Pyridine / Heteroaromatic compound / Azacycle / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organonitrogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
phenanthroline (CHEBI:44975) / a small molecule (O-PHENANTHROLINE)

Targets

Kind
Protein
Organism
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
Unknown
General Function
Transmembrane signaling receptor activity
Specific Function
Receptor for the attractant L-aspartate and related amino and dicarboxylic acids. Tar mediates taxis away from the repellents cobalt and nickel. Unlike in E.coli tar, it does not mediates maltose t...
Gene Name
tar
Uniprot ID
P02941
Uniprot Name
Methyl-accepting chemotaxis protein II
Molecular Weight
59613.55 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]
Kind
Protein
Organism
Pseudomonas maltophilia
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Has a high activity against imipenem.
Gene Name
Not Available
Uniprot ID
P52700
Uniprot Name
Metallo-beta-lactamase L1
Molecular Weight
30800.635 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 June 13, 2005 07:24 / Updated on November 02, 2018 05:16