1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine (CHEM003541)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2014-09-05 17:10:34 UTC
Update Date2026-04-14 17:22:47 UTC
Accession NumberCHEM003541
Identification
Common Name1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine
ClassSmall Molecule
Description1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine is a food-related mutagen, reported to be the most abundant heterocyclic amine found in cooked meat and fish.
Contaminant Sources
  • FooDB Chemicals
  • IARC Carcinogens Group 2B
  • Suspected Compounds
  • T3DB toxins
  • Tobacco Smoke Compounds
Contaminant Type
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridineChEBI
PhIPKegg
1-Methyl-6-phenyl-1H-imidazo(4,5-b)pyridin-2-amineHMDB
1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine, 9ciHMDB
1H-imidazo(4,5-b)Pyridin-2-amine, 1-methyl-6-phenyl- (9ci)HMDB
1H-imidazo(4,5-b)PyridineHMDB
2-amino-1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridineHMDB
2-amino-1-Methyl-6-phenyl-imidazo [4,5-b] pyridineHMDB
2-amino-1-Methyl-6-phenyl-imidazo(4,5-b)pyridineHMDB
2-amino-1-Methyl-6-phenylimidazo [4,5-b]pyridine (phip)HMDB
2-amino-1-Methyl-6-phenylimidazo(4,5-b)pyridineHMDB
PIQHMDB
Chemical FormulaC13H12N4
Average Molecular Mass224.261 g/mol
Monoisotopic Mass224.106 g/mol
CAS Registry Number105650-23-5
IUPAC Name1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine
Traditional NamePHIP
SMILESCN1C(N)=NC2=NC=C(C=C12)C1=CC=CC=C1
InChI IdentifierInChI=1S/C13H12N4/c1-17-11-7-10(9-5-3-2-4-6-9)8-15-12(11)16-13(17)14/h2-8H,1H3,(H2,14,15,16)
InChI KeyUQVKZNNCIHJZLS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPhenylpyridines
Direct ParentPhenylpyridines
Alternative Parents
Substituents
  • 3-phenylpyridine
  • Imidazopyridine
  • Aminoimidazole
  • Monocyclic benzene moiety
  • Benzenoid
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Azacycle
  • Primary amine
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point327 - 328 °C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.42 g/LALOGPS
logP2.27ALOGPS
logP2.09ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)5.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area56.73 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity68.59 m³·mol⁻¹ChemAxon
Polarizability24.68 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-0920000000-32d0b5e415e1105fc11eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-0090000000-efb76bf58f3994016cf1Spectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , negativesplash10-0a4i-0090000000-b8fb35b55ad155cc7927Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-0090000000-f3cfae76fa7ac8760463Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-004i-0090000000-19ebcab9e92cf28fe665Spectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-004i-0090000000-d014b289386a8225dce2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-0390000000-efc7b323d1240ec77888Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0090000000-e7f426127c2726473d3aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-b0731c54552edfaa492cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-4a6722fa7901af950403Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-795c6af07fd6e997db24Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-08gl-0940000000-62a471c55164009e49beSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0090000000-14b4e6ecfa39851cca8fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-0590000000-c9e23c1f63a2e53fc79bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00di-0090000000-efb76bf58f3994016cf1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0aor-0690000000-9739d23813875694729bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-0090000000-65edd723a705a1d2e619Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-0090000000-bb679c2d35a08dca18d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-67088fd3b417e1d0bef4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0290000000-1b47a5b6342c93cf2ecaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7p-2900000000-4ee091a2980f3c633154Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-040c51d2814aa27e5d4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0290000000-e95cf8ae6c1cc45d7dd1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-7590000000-fc5adb24f630eb8862d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-e6ea8a2bee2c908d8287Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-6c404117ca122f8083a7Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (2)
Uses/Sources1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine is a food-related mutagen, reported to be the most abundant heterocyclic amine found in cooked meat and fish.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB08398
HMDB IDHMDB0041008
FooDB IDFDB020870
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDPIQ
Wikipedia Link2-Amino-1-methyl-6-phenylimidazo(4,5-b)pyridine
Chemspider ID1476
ChEBI ID76290
PubChem Compound ID1530
Kegg Compound IDC16038
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10944558
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11921178
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20036730
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23265474
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23306951
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23313794
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23466459
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24128508
9. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.