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Showing NP-Card for 2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline (NP0336823)

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Record Information
Version2.0
Created at2024-09-11 07:58:47 UTC
Updated at2024-09-11 07:58:47 UTC
NP-MRD IDNP0336823
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline
Description2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline, also known as 8-meiqx or 8-methyl-iqx, belongs to the class of organic compounds known as quinoxalines. Quinoxalines are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring. 2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline is a strong basic compound (based on its pKa). 2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline was first documented in 2012 (PMID: 22138251). 2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline is a potentially toxic compound (PMID: 23600962) (PMID: 23624435) (PMID: 23681119) (PMID: 23810796).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0336823 (2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline)


  Mrv0541 02241215172D          

 16 18  0  0  0  0            999 V2000
    2.4283    0.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184    0.4045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4283   -0.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6192   -0.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4572   -1.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7281   -1.8613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0810   -1.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6474   -1.5374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2945   -1.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1326   -0.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3235   -0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429   -0.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0520   -0.2433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3235    0.8091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1326    1.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3759    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 10  1  0  0  0  0
  2 15  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  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
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
M  END
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3D MOL for NP0336823 (2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline)

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3D SDF for NP0336823 (2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline)

  Mrv0541 02241215172D          

 16 18  0  0  0  0            999 V2000
    2.4283    0.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184    0.4045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4283   -0.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6192   -0.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4572   -1.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7281   -1.8613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0810   -1.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6474   -1.5374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2945   -1.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1326   -0.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3235   -0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429   -0.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0520   -0.2433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3235    0.8091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1326    1.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3759    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 10  1  0  0  0  0
  2 15  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  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
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336823

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(N)=NC2=C1C=CC1=C2N=C(C)C=N1

> <INCHI_IDENTIFIER>
InChI=1S/C11H11N5/c1-6-5-13-7-3-4-8-10(9(7)14-6)15-11(12)16(8)2/h3-5H,1-2H3,(H2,12,15)

> <INCHI_KEY>
DVCCCQNKIYNAKB-UHFFFAOYSA-N

> <FORMULA>
C11H11N5

> <MOLECULAR_WEIGHT>
213.2385

> <EXACT_MASS>
213.101445377

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
22.95580438437837

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-amine

> <ALOGPS_LOGP>
1.34

> <JCHEM_LOGP>
0.7957068386666666

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.76072436491985

> <JCHEM_POLAR_SURFACE_AREA>
69.62

> <JCHEM_REFRACTIVITY>
60.02279999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,8-dimethylimidazo[4,5-f]quinoxalin-2-amine

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0336823 (2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline)
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PDB for NP0336823 (2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline)
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       4.533   0.755   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.021   0.755   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -4.533  -1.058   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.023  -1.510   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.720  -3.022   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -1.359  -3.474   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -0.151  -2.417   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.209  -2.870   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.416  -1.964   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.114  -0.454   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.604  -0.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.453  -0.906   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -1.964  -0.454   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       0.604   1.510   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.114   1.963   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       2.568   3.474   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1   10   15                                                  
CONECT    3    4                                                            
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    2    9   11                                                  
CONECT   11   10   12   14                                                  
CONECT   12    7   11   13                                                  
CONECT   13    4   12                                                       
CONECT   14   11   15                                                       
CONECT   15    2   14   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

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3D PDB for NP0336823 (2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline)
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SMILES for NP0336823 (2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline)
CN1C(N)=NC2=C1C=CC1=C2N=C(C)C=N1
Download
INCHI for NP0336823 (2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline)
InChI=1S/C11H11N5/c1-6-5-13-7-3-4-8-10(9(7)14-6)15-11(12)16(8)2/h3-5H,1-2H3,(H2,12,15)
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View in JSmol
Synonyms
ValueSource
2-Amino-3,8-dimethyl-3H-imidazo(4,5-F)quinoxalineChEBI
2-Amino-3,8-dimethylimidazo[4,5-F]quinoxalineChEBI
8-MeIQXChEBI
8-Methyl-iqxChEBI
2-Amino-3,8-dimethylimidazo(4,5-F)quinoxalineHMDB
2-Amino-3,8-dimethylimidazo[4,5-F ]quinoxalineHMDB
3,8-DiMeIQXHMDB
3,8-Dimethyl-3H-imidazo(4,5-F)quinoxalin-2-amineHMDB
3,8-Dimethyl-3H-imidazo[4,5-F]quinoxalin-2-amineHMDB
3,8-Dimethyl-3H-imidazo[4,5-F]quinoxalin-2-amine, 9ciHMDB
3,8-Dimethylimidazo(4,5-F)quinoxaline-2-amineHMDB
Me-iqxHMDB
MeIQxHMDB
Meiqx CPDHMDB
Chemical FormulaC11H11N5
Average Mass213.2385 Da
Monoisotopic Mass213.10145 Da
IUPAC Name3,8-dimethyl-3H-imidazo[4,5-f]quinoxalin-2-amine
Traditional Name3,8-dimethylimidazo[4,5-f]quinoxalin-2-amine
CAS Registry NumberNot Available
SMILES
CN1C(N)=NC2=C1C=CC1=C2N=C(C)C=N1
InChI Identifier
InChI=1S/C11H11N5/c1-6-5-13-7-3-4-8-10(9(7)14-6)15-11(12)16(8)2/h3-5H,1-2H3,(H2,12,15)
InChI KeyDVCCCQNKIYNAKB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinoxalines. Quinoxalines are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassDiazanaphthalenes  
Sub ClassBenzodiazines  
Direct ParentQuinoxalines  
Alternative Parents
Substituents
  • Quinoxaline
    • 

  • Benzimidazole
    • 

  • Aminoimidazole
    • 

  • Benzenoid
    • 

  • Pyrazine
    • 

  • 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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.34ALOGPS
logP0.8ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)4.76ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.62 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity60.02 m³·mol⁻¹ChemAxon
Polarizability22.96 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029864  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001093  
KNApSAcK IDNot Available
Chemspider ID56076  
KEGG Compound IDC19255  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62275  
PDB IDNot Available
ChEBI ID76604  
Good Scents IDNot Available
References
General References
  1. Viegas O, Zegura B, Pezdric M, Novak M, Ferreira IM, Pinho O, Filipic M: Protective effects of xanthohumol against the genotoxicity of heterocyclic aromatic amines MeIQx and PhIP in bacteria and in human hepatoma (HepG2) cells. Food Chem Toxicol. 2012 Mar;50(3-4):949-55. doi: 10.1016/j.fct.2011.11.031. Epub  2011 Nov 26. [PubMed:22138251  ] 
  2. Gibis M, Weiss J: Formation of heterocyclic amines in salami and ham pizza toppings during baking of frozen pizza. J Food Sci. 2013 Jun;78(6):C832-8. doi: 10.1111/1750-3841.12121. Epub 2013 Apr  19. [PubMed:23600962  ] 
  3. Rounds L, Havens CM, Feinstein Y, Friedman M, Ravishankar S: Concentration-dependent inhibition of Escherichia coli O157:H7 and heterocyclic amines in heated ground beef patties by apple and olive extracts, onion powder and clove bud oil. Meat Sci. 2013 Aug;94(4):461-7. doi: 10.1016/j.meatsci.2013.03.010. Epub 2013 Mar  15. [PubMed:23624435  ] 
  4. Kuroda K, Kijima A, Ishii Y, Takasu S, Jin M, Matsushita K, Kodama Y, Umemura T: Flumequine enhances the in vivo mutagenicity of MeIQx in the mouse liver. Arch Toxicol. 2013 Aug;87(8):1609-19. doi: 10.1007/s00204-013-1064-y. Epub 2013  May 17. [PubMed:23681119  ] 
  5. Pezdirc M, Zegura B, Filipic M: Genotoxicity and induction of DNA damage responsive genes by food-borne heterocyclic aromatic amines in human hepatoma HepG2 cells. Food Chem Toxicol. 2013 Sep;59:386-94. doi: 10.1016/j.fct.2013.06.030. Epub 2013  Jun 28. [PubMed:23810796  ]