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

Record Information
Version1.0
Creation Date2014-09-05 17:10:34 UTC
Update Date2026-08-18 23:05:33 UTC
Accession NumberCHEM003541
Identification
Common Name1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine
ClassSmall Molecule
Description
1-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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
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
External Links
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.