NP-MRD: Showing NP-Card for 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine (NP0336534)

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Record Information

Version

2.0

Created at

2024-09-11 06:44:59 UTC

Updated at

2024-09-11 06:44:59 UTC

NP-MRD ID

NP0336534

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine, also known as phip or 1H-imidazo(4,5-b)pyridin-2-amine, 1-methyl-6-phenyl- (9ci), 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 very strong basic compound (based on its pKa). 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine was first documented in 2000 (PMID: 10944558). 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 (PMID: 11921178) (PMID: 20036730) (PMID: 23265474) (PMID: 23306951).

Structure

MOL SDF PDB SMILES InChI

PIQ
  Mrv0541 02241214042D          

 17 19  0  0  0  0            999 V2000
   -2.8024   -0.7118    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9774   -0.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4925   -0.0443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7079   -0.2993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0066    0.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211   -0.2993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4355    0.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4355    0.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1500    1.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8645    0.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8645    0.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1500   -0.2993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4925   -1.3792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7474    0.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7079   -1.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0066   -1.5368    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211   -1.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 13  2  0  0  0  0
  3  4  1  0  0  0  0
  3 14  1  0  0  0  0
  4  5  2  0  0  0  0
  4 15  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 17  2  0  0  0  0
  7  8  1  0  0  0  0
  7 12  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336534

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
UQVKZNNCIHJZLS-UHFFFAOYSA-N

> <FORMULA>
C13H12N4

> <MOLECULAR_WEIGHT>
224.2612

> <EXACT_MASS>
224.106196404

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.676243540354662

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
2.093061605

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.434517950913985

> <JCHEM_POLAR_SURFACE_AREA>
56.730000000000004

> <JCHEM_REFRACTIVITY>
68.59100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
PHIP

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PIQ                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0      -5.231  -1.329   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -3.691  -1.329   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -2.786  -0.083   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.321  -0.559   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.012   0.211   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.346  -0.559   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.680   0.211   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.680   1.751   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.013   2.521   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.347   1.751   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.347   0.211   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.013  -0.559   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -2.786  -2.575   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -3.262   1.382   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.321  -2.099   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       0.012  -2.869   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       1.346  -2.099   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    7   11                                                       
CONECT   13    2   15                                                       
CONECT   14    3                                                            
CONECT   15    4   13   16                                                  
CONECT   16   15   17                                                       
CONECT   17    6   16                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine	ChEBI
PhIP	Kegg
1-Methyl-6-phenyl-1H-imidazo(4,5-b)pyridin-2-amine	HMDB
1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine, 9ci	HMDB
1H-Imidazo(4,5-b)pyridin-2-amine, 1-methyl-6-phenyl- (9ci)	HMDB
1H-Imidazo(4,5-b)pyridine	HMDB
2-Amino-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine	HMDB
2-Amino-1-methyl-6-phenyl-imidazo [4,5-b] pyridine	HMDB
2-Amino-1-methyl-6-phenyl-imidazo(4,5-b)pyridine	HMDB
2-Amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (phip)	HMDB
2-Amino-1-methyl-6-phenylimidazo(4,5-b)pyridine	HMDB
PIQ	HMDB

Chemical Formula

C₁₃H₁₂N₄

Average Mass

224.2612 Da

Monoisotopic Mass

224.10620 Da

IUPAC Name

1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine

Traditional Name

PHIP

CAS Registry Number

Not Available

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 Key

UQVKZNNCIHJZLS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Phenylpyridines

Direct Parent

Phenylpyridines

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

primary amino compound (CHEBI:76290 )
imidazopyridine (CHEBI:76290 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.27	ALOGPS
logP	2.09	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	5.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	56.73 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.59 m³·mol⁻¹	ChemAxon
Polarizability	24.68 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0041008

DrugBank ID

DB08398

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020870

KNApSAcK ID

Not Available

Chemspider ID

1476

KEGG Compound ID

C16038

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Amino-1-methyl-6-phenylimidazo(4,5-b)pyridine

METLIN ID

Not Available

PubChem Compound

1530

PDB ID

PIQ

ChEBI ID

76290

Good Scents ID

Not Available

References

General References

Sinha R, Gustafson DR, Kulldorff M, Wen WQ, Cerhan JR, Zheng W: 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, a carcinogen in high-temperature-cooked meat, and breast cancer risk. J Natl Cancer Inst. 2000 Aug 16;92(16):1352-4. doi: 10.1093/jnci/92.16.1352. [PubMed:10944558 ]
Felton JS, Knize MG, Salmon CP, Malfatti MA, Kulp KS: Human exposure to heterocyclic amine food mutagens/carcinogens: relevance to breast cancer. Environ Mol Mutagen. 2002;39(2-3):112-8. doi: 10.1002/em.10070. [PubMed:11921178 ]
Evans RM, Rahte S, Kortenkamp A: Inability to confirm estrogenicity of the heterocyclic amine PhIP in two in vitro assays. Toxicol In Vitro. 2010 Sep;24(6):1757-63. doi: 10.1016/j.tiv.2009.12.017. Epub 2009 Dec 29. [PubMed:20036730 ]
Zamora R, Alcon E, Hidalgo FJ: Comparative formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in creatinine/phenylalanine and creatinine/phenylalanine/4-oxo-2-nonenal reaction mixtures. Food Chem. 2013 May 1;138(1):180-5. doi: 10.1016/j.foodchem.2012.09.116. Epub 2012 Nov 8. [PubMed:23265474 ]
Nicken P, Schroder B, von Keutz A, Breves G, Steinberg P: The colon carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) is actively secreted in the distal colon of the rat: an integrated view on the role of PhIP transport and metabolism in PhIP-induced colon carcinogenesis. Arch Toxicol. 2013 May;87(5):895-904. doi: 10.1007/s00204-012-1006-0. Epub 2013 Jan 10. [PubMed:23306951 ]

Showing NP-Card for 1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine (NP0336534)

MOL for NP0336534 (1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine)

3D MOL for NP0336534 (1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine)

3D SDF for NP0336534 (1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine)

3D-SDF for NP0336534 (1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine)

PDB for NP0336534 (1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine)

3D PDB for NP0336534 (1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine)

SMILES for NP0336534 (1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine)

INCHI for NP0336534 (1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine)

Structure for NP0336534 (1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine)

3D Structure for NP0336534 (1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine)