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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:38:25 UTC
Update Date2022-03-07 02:56:50 UTC
HMDB IDHMDB0041008
Secondary Accession Numbers
  • HMDB41008
Metabolite Identification
Common Name1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine
Description1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine, also known as phip, 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. 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Based on a literature review a significant number of articles have been published on 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine.
Structure
Data?1563863614
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 Weight224.2612
Monoisotopic Molecular Weight224.106196404
IUPAC Name1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine
Traditional NamePHIP
CAS Registry Number105650-23-5
SMILES
CN1C(N)=NC2=NC=C(C=C12)C1=CC=CC=C1
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point327 - 328 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.23Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+152.12531661259
DarkChem[M-H]-151.95731661259
DeepCCS[M-2H]-184.23230932474
DeepCCS[M+Na]+159.35330932474
AllCCS[M+H]+151.232859911
AllCCS[M+H-H2O]+147.032859911
AllCCS[M+NH4]+155.132859911
AllCCS[M+Na]+156.332859911
AllCCS[M-H]-155.432859911
AllCCS[M+Na-2H]-155.032859911
AllCCS[M+HCOO]-154.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amineCN1C(N)=NC2=NC=C(C=C12)C1=CC=CC=C13379.3Standard polar33892256
1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amineCN1C(N)=NC2=NC=C(C=C12)C1=CC=CC=C12354.3Standard non polar33892256
1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amineCN1C(N)=NC2=NC=C(C=C12)C1=CC=CC=C12631.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine,1TMS,isomer #1CN1C(N[Si](C)(C)C)=NC2=NC=C(C3=CC=CC=C3)C=C212476.9Semi standard non polar33892256
1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine,1TMS,isomer #1CN1C(N[Si](C)(C)C)=NC2=NC=C(C3=CC=CC=C3)C=C212434.9Standard non polar33892256
1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine,2TMS,isomer #1CN1C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=NC=C(C3=CC=CC=C3)C=C212418.6Semi standard non polar33892256
1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine,2TMS,isomer #1CN1C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=NC=C(C3=CC=CC=C3)C=C212557.2Standard non polar33892256
1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine,1TBDMS,isomer #1CN1C(N[Si](C)(C)C(C)(C)C)=NC2=NC=C(C3=CC=CC=C3)C=C212712.9Semi standard non polar33892256
1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine,1TBDMS,isomer #1CN1C(N[Si](C)(C)C(C)(C)C)=NC2=NC=C(C3=CC=CC=C3)C=C212650.0Standard non polar33892256
1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine,2TBDMS,isomer #1CN1C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=NC=C(C3=CC=CC=C3)C=C212827.2Semi standard non polar33892256
1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine,2TBDMS,isomer #1CN1C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=NC=C(C3=CC=CC=C3)C=C212971.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-0920000000-32d0b5e415e1105fc11e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine LC-ESI-QFT , negative-QTOFsplash10-00di-0090000000-efb76bf58f3994016cf12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine APCI-ITFT , negative-QTOFsplash10-0a4i-0090000000-b8fb35b55ad155cc79272017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine LC-ESI-QFT , positive-QTOFsplash10-004i-0090000000-f3cfae76fa7ac87604632017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine ESI-ITFT , positive-QTOFsplash10-004i-0090000000-19ebcab9e92cf28fe6652017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine APCI-ITFT , positive-QTOFsplash10-004i-0090000000-d014b289386a8225dce22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 40V, Positive-QTOFsplash10-03di-0390000000-efc7b323d1240ec778882021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 30V, Positive-QTOFsplash10-004i-0090000000-e7f426127c2726473d3a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 10V, Positive-QTOFsplash10-004i-0090000000-b0731c54552edfaa492c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 20V, Positive-QTOFsplash10-004i-0090000000-4a6722fa7901af9504032021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 10V, Negative-QTOFsplash10-00di-0090000000-795c6af07fd6e997db242021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 50V, Positive-QTOFsplash10-08gl-0940000000-62a471c55164009e49be2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 20V, Negative-QTOFsplash10-0a4i-0090000000-14b4e6ecfa39851cca8f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 30V, Negative-QTOFsplash10-0a4i-0590000000-c9e23c1f63a2e53fc79b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 35V, Negative-QTOFsplash10-00di-0090000000-efb76bf58f3994016cf12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 40V, Negative-QTOFsplash10-0aor-0690000000-9739d23813875694729b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 35V, Positive-QTOFsplash10-004i-0090000000-65edd723a705a1d2e6192021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 35V, Positive-QTOFsplash10-004i-0090000000-bb679c2d35a08dca18d52021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 10V, Positive-QTOFsplash10-004i-0090000000-67088fd3b417e1d0bef42016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 20V, Positive-QTOFsplash10-004i-0290000000-1b47a5b6342c93cf2eca2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 40V, Positive-QTOFsplash10-0f7p-2900000000-4ee091a2980f3c6331542016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 10V, Negative-QTOFsplash10-00di-0090000000-040c51d2814aa27e5d4e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 20V, Negative-QTOFsplash10-00di-0290000000-e95cf8ae6c1cc45d7dd12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 40V, Negative-QTOFsplash10-0a4l-7590000000-fc5adb24f630eb8862d92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 10V, Positive-QTOFsplash10-004i-0090000000-e6ea8a2bee2c908d82872021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine 20V, Positive-QTOFsplash10-004i-0090000000-6c404117ca122f8083a72021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08398
Phenol Explorer Compound IDNot Available
FooDB IDFDB020870
KNApSAcK IDNot Available
Chemspider ID1476
KEGG Compound IDC16038
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Amino-1-methyl-6-phenylimidazo(4,5-b)pyridine
METLIN IDNot Available
PubChem Compound1530
PDB IDPIQ
ChEBI ID76290
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .