1,10-Phenanthroline (CHEM003772)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (6)XML
Record Information
Version1.0
Creation Date2014-09-11 05:17:48 UTC
Update Date2016-11-09 01:09:13 UTC
Accession NumberCHEM003772
Identification
Common Name1,10-Phenanthroline
ClassSmall Molecule
DescriptionPhenanthroline is a heterocyclic organic compound. 1,10-Phenanthroline is an inhibitor of metallopeptidases, especially carboxypeptidase A. Inhibition of the enzyme occurs by removal and chelation of the metal ion required for catalytic activity, leaving an inactive apoenzyme. 1,10-Phenanthroline targets mainly zinc metallopeptidases, with a much lower affinity for calcium metallopeptidases.
Contaminant Sources
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • Suspected Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Industrial/Workplace Toxin
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4,5-DiazaphenanthreneChEBI
O-PhenanthrolineChEBI
OrthophenanthrolineChEBI
PhenChEBI
(OP)2Cu(I)HMDB
1,10-Phenanthroline monohydrochorideHMDB
5,6-Dihydro-1,10-phenanthrolineHMDB
1,10-Phenanthroline, zinc saltHMDB
O-PHEHMDB
1,10-Phenanthroline hydrateHMDB
1,10-Phenanthroline monoperchlorateHMDB
Copper phenanthrolineHMDB
1,10-Phenanthroline hydrochorideHMDB
Chemical FormulaC12H8N2
Average Molecular Mass180.205 g/mol
Monoisotopic Mass180.069 g/mol
CAS Registry Number66-71-7
IUPAC Name1,10-phenanthroline
Traditional Namephen
SMILESC1=CC2=CC=C3C=CC=NC3=C2N=C1
InChI IdentifierInChI=1S/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H
InChI KeyDGEZNRSVGBDHLK-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPhenanthrolines
Sub ClassNot Available
Direct ParentPhenanthrolines
Alternative Parents
Substituents
  • 1,10-phenanthroline
  • Quinoline
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point117°C
Boiling Point> 300°C
Solubility2690 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP2.31ALOGPS
logP2.29ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.78 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity53.9 m³·mol⁻¹ChemAxon
Polarizability19.26 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fai-1900000000-8bf54d7a505254cd0f42Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-003r-1900000000-bf66a4d49c83dd24535eSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-003r-4900000000-e878f31ffa5b4af39dfdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-0900000000-eb76a0de05170e5f9daeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-7bdef677e6a80f05aa75Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-555e8d3f751a47049c5aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-c48df88a05c1dbab0adcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-07ee18512e76f5b25dd1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0fb9-0900000000-7a08b5b37861250df6bdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-94a0600a96f48f8aa145Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0fc0-0900000000-0f2b71fb75d6e9f09b6cSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-29a83efe3a4c61b6e760Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-f6eedb340d4cf4ab269fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-b8ee2e5a776aecb532caSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-00di-0900000000-88682d0eaadc3985ae6fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-5c3af3894358cf9d55fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-29a83efe3a4c61b6e760Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-e7952d19ca3578ac4501Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-e7952d19ca3578ac4501Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-62142b81fd0b92ba0c9dSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-9cbaa490715b11601fdcSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-7095641d365002c9b143Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0f89-0900000000-c2a7113134a8fdaed496Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-5c90552c85b31b9dad6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-f502dd2cb1f00efc87a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-0900000000-021477966b1a0bb96171Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-d57b0da7ada8a8dbc26aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-d57b0da7ada8a8dbc26aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-ca2e0248fd9a1a0d0424Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-1900000000-e3edab983e41e183110aSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB02365
HMDB IDHMDB0244053
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPhenanthroline
Chemspider ID1278
ChEBI ID44975
PubChem Compound ID1318
Kegg Compound IDC00604
YMDB IDNot Available
ECMDB IDECMDB20221
References
Synthesis Reference

Judith N. Burstyn, Omar Green, Bhavesh A. Gandhi, “BISCOPPER COMPLEXES, METHODS OF SYNTHESIS, AND USES THEROF.” U.S. Patent US20080206890, issued August 28, 2008.

MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11170445
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18499511
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=6140164
4. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.