NP-MRD: Showing NP-Card for 2-Amino-3,4-dimethylimidazo[4,5-f]quinoline (NP0337849)

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Record Information

Version

2.0

Created at

2024-09-11 12:43:45 UTC

Updated at

2024-09-11 12:43:45 UTC

NP-MRD ID

NP0337849

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Amino-3,4-dimethylimidazo[4,5-f]quinoline

Description

2-Amino-3,4-dimethylimidazo[4,5-f]quinoline, also known as me-iq or MELQ, belongs to the class of organic compounds known as quinolines and derivatives. Quinolines and derivatives are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene. 2-Amino-3,4-dimethylimidazo[4,5-f]quinoline is a very strong basic compound (based on its pKa). Outside of the human body, 2-Amino-3,4-dimethylimidazo[4,5-f]quinoline has been detected, but not quantified in, fishes. This could make 2-amino-3,4-dimethylimidazo[4,5-F]quinoline a potential biomarker for the consumption of these foods. 2-Amino-3,4-dimethylimidazo[4,5-f]quinoline is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241218512D          

 16 18  0  0  0  0            999 V2000
    1.6994   -1.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8904   -1.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3232   -1.5374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4851   -1.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0516   -1.8613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8613   -1.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0233   -0.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3755   -0.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6470   -0.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007   -0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7285   -0.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0233    0.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2143    0.4045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007    0.8091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7285    1.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9710    1.8613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 11  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 14  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337849

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(N)=NC2=C1C(C)=CC1=C2C=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C12H12N4/c1-7-6-9-8(4-3-5-14-9)10-11(7)16(2)12(13)15-10/h3-6H,1-2H3,(H2,13,15)

> <INCHI_KEY>
GMGWMIJIGUYNAY-UHFFFAOYSA-N

> <FORMULA>
C12H12N4

> <MOLECULAR_WEIGHT>
212.2505

> <EXACT_MASS>
212.106196404

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.290720789025016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4-dimethyl-3H-imidazo[4,5-f]quinolin-2-amine

> <ALOGPS_LOGP>
1.75

> <JCHEM_LOGP>
2.009580160333333

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.975540802278499

> <JCHEM_POLAR_SURFACE_AREA>
56.730000000000004

> <JCHEM_REFRACTIVITY>
63.0014

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.86e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dimethylimidazo[4,5-f]quinolin-2-amine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.172  -2.417   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.662  -1.964   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.603  -2.870   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.906  -2.417   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.963  -3.474   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -3.474  -3.022   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.777  -1.510   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.568  -0.454   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.208  -0.906   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.001  -0.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.360  -0.454   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.777   0.755   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       2.267   0.755   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       0.001   1.510   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       1.360   1.963   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       1.812   3.474   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    4    8   10                                                  
CONECT   10    9   11   14                                                  
CONECT   11    2   10   13                                                  
CONECT   12   13                                                            
CONECT   13   11   12   15                                                  
CONECT   14   10   15                                                       
CONECT   15   13   14   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Value	Source
2-Amino-3,4-dimethyl-3H-imidazo(4,5-F)quinoline	HMDB
2-Amino-3,4-dimethyl-3H-imidazo[4,5-F]quinoline	HMDB
2-Amino-3,4-dimethylimidazo(4,5-F)quinoline	HMDB
3,4-Dimethyl-3H-imidazo(4,5-F)quinolin-2-amine	HMDB
3,4-Dimethyl-3H-imidazo[4,5-F]quinolin-2-amine	HMDB
Me iq	HMDB
Me-iq	HMDB
MELQ	HMDB
Methyl iq	HMDB
Methyl-iq	HMDB
MeIQ	MeSH
2-amino-3,4-dimethylimidazo[4,5-F]Quinoline	KEGG

Chemical Formula

C₁₂H₁₂N₄

Average Mass

212.2505 Da

Monoisotopic Mass

212.10620 Da

IUPAC Name

3,4-dimethyl-3H-imidazo[4,5-f]quinolin-2-amine

Traditional Name

3,4-dimethylimidazo[4,5-f]quinolin-2-amine

CAS Registry Number

Not Available

SMILES

CN1C(N)=NC2=C1C(C)=CC1=C2C=CC=N1

InChI Identifier

InChI=1S/C12H12N4/c1-7-6-9-8(4-3-5-14-9)10-11(7)16(2)12(13)15-10/h3-6H,1-2H3,(H2,13,15)

InChI Key

GMGWMIJIGUYNAY-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 quinolines and derivatives. Quinolines and derivatives are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Not Available

Direct Parent

Quinolines and derivatives

Alternative Parents

Substituents

Quinoline
Benzimidazole
Benzenoid
Pyridine
N-substituted imidazole
Heteroaromatic compound
Imidazole
Azole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aminoquinoline (CHEBI:82338 )

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	1.75	ALOGPS
logP	2.01	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	7.98	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	56.73 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	63 m³·mol⁻¹	ChemAxon
Polarizability	23.29 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

HMDB0029707

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000901

KNApSAcK ID

Not Available

Chemspider ID

56075

KEGG Compound ID

C19254

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62274

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-Amino-3,4-dimethylimidazo[4,5-f]quinoline (NP0337849)

MOL for NP0337849 (2-Amino-3,4-dimethylimidazo[4,5-f]quinoline)

3D MOL for NP0337849 (2-Amino-3,4-dimethylimidazo[4,5-f]quinoline)

3D SDF for NP0337849 (2-Amino-3,4-dimethylimidazo[4,5-f]quinoline)

3D-SDF for NP0337849 (2-Amino-3,4-dimethylimidazo[4,5-f]quinoline)

PDB for NP0337849 (2-Amino-3,4-dimethylimidazo[4,5-f]quinoline)

3D PDB for NP0337849 (2-Amino-3,4-dimethylimidazo[4,5-f]quinoline)

SMILES for NP0337849 (2-Amino-3,4-dimethylimidazo[4,5-f]quinoline)

INCHI for NP0337849 (2-Amino-3,4-dimethylimidazo[4,5-f]quinoline)

Structure for NP0337849 (2-Amino-3,4-dimethylimidazo[4,5-f]quinoline)

3D Structure for NP0337849 (2-Amino-3,4-dimethylimidazo[4,5-f]quinoline)