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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:55:01 UTC

Update Date

2021-09-26 23:03:36 UTC

HMDB ID

HMDB0251552

Secondary Accession Numbers

None

Metabolite Identification

Common Name

6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione

Description

FG-9041 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. FG-9041 is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). 6,7-dinitro-1,4-dihydroquinoxaline-2,3-dione is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv1572004091616262D          

 18 19  0  0  0  0            999 V2000
   -0.3572   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -0.8250    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -1.6500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.7861    0.8250    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    1.6500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.0716    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18  2  1  0  0  0  0
M  CHG  4   7   1   9  -1  10   1  12  -1
M  END
> <DATABASE_ID>
HMDB0251552

> <DATABASE_NAME>
hmdb

> <SMILES>
[O-][N+](=O)C1=C(C=C2NC(=O)C(=O)NC2=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H4N4O6/c13-7-8(14)10-4-2-6(12(17)18)5(11(15)16)1-3(4)9-7/h1-2H,(H,9,13)(H,10,14)

> <INCHI_KEY>
RWVIMCIPOAXUDG-UHFFFAOYSA-N

> <FORMULA>
C8H4N4O6

> <MOLECULAR_WEIGHT>
252.142

> <EXACT_MASS>
252.013083865

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
20.02389313990798

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,7-dinitro-1,2,3,4-tetrahydroquinoxaline-2,3-dione

> <ALOGPS_LOGP>
0.43

> <JCHEM_LOGP>
0.5115747886666666

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.895721155385065

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.529245802633358

> <JCHEM_PKA_STRONGEST_BASIC>
-6.210979305789252

> <JCHEM_POLAR_SURFACE_AREA>
144.48

> <JCHEM_REFRACTIVITY>
57.576200000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
DNQX

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-APR-16         0                                  
HETATM    1  C   UNK     0      -0.667  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.667  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.667   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.001   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -3.334  -1.540   0.000  0.00  0.00           N+1
HETATM    8  O   UNK     0      -4.668  -0.770   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -3.334  -3.080   0.000  0.00  0.00           O-1
HETATM   10  N   UNK     0      -3.334   1.540   0.000  0.00  0.00           N+1
HETATM   11  O   UNK     0      -4.668   0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -3.334   3.080   0.000  0.00  0.00           O-1
HETATM   13  N   UNK     0       2.000   1.540   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       3.334   0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.668   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.668  -1.540   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0       2.000  -1.540   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    3   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    2                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6,7-Dinitroquinoxaline-2,3-dione	MeSH
DNQX	MeSH

Chemical Formula

C₈H₄N₄O₆

Average Molecular Weight

252.142

Monoisotopic Molecular Weight

252.013083865

IUPAC Name

6,7-dinitro-1,2,3,4-tetrahydroquinoxaline-2,3-dione

Traditional Name

DNQX

CAS Registry Number

Not Available

SMILES

[O-][N+](=O)C1=C(C=C2NC(=O)C(=O)NC2=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C8H4N4O6/c13-7-8(14)10-4-2-6(12(17)18)5(11(15)16)1-3(4)9-7/h1-2H,(H,9,13)(H,10,14)

InChI Key

RWVIMCIPOAXUDG-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinoxalines

Alternative Parents

Substituents

Quinoxaline
Nitroaromatic compound
Pyrazine
Benzenoid
Heteroaromatic compound
Lactam
C-nitro compound
Organic nitro compound
Organic oxoazanium
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.43	ALOGPS
logP	0.51	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.53	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	144.48 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	57.58 m³·mol⁻¹	ChemAxon
Polarizability	20.02 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	147.181	30932474
DeepCCS	[M-H]-	144.823	30932474
DeepCCS	[M-2H]-	177.731	30932474
DeepCCS	[M+Na]+	153.529	30932474
AllCCS	[M+H]+	149.7	32859911
AllCCS	[M+H-H2O]+	145.9	32859911
AllCCS	[M+NH4]+	153.2	32859911
AllCCS	[M+Na]+	154.2	32859911
AllCCS	[M-H]-	146.1	32859911
AllCCS	[M+Na-2H]-	145.4	32859911
AllCCS	[M+HCOO]-	144.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione	[O-][N+](=O)C1=C(C=C2NC(=O)C(=O)NC2=C1)[N+]([O-])=O	3378.1	Standard polar	33892256
6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione	[O-][N+](=O)C1=C(C=C2NC(=O)C(=O)NC2=C1)[N+]([O-])=O	2422.1	Standard non polar	33892256
6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione	[O-][N+](=O)C1=C(C=C2NC(=O)C(=O)NC2=C1)[N+]([O-])=O	2930.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione,1TMS,isomer #1	C[Si](C)(C)N1C(=O)C(=O)[NH]C2=CC([N+](=O)[O-])=C([N+](=O)[O-])C=C21	2445.3	Semi standard non polar	33892256
6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione,1TMS,isomer #1	C[Si](C)(C)N1C(=O)C(=O)[NH]C2=CC([N+](=O)[O-])=C([N+](=O)[O-])C=C21	2328.7	Standard non polar	33892256
6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione,1TMS,isomer #1	C[Si](C)(C)N1C(=O)C(=O)[NH]C2=CC([N+](=O)[O-])=C([N+](=O)[O-])C=C21	3375.8	Standard polar	33892256
6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione,2TMS,isomer #1	C[Si](C)(C)N1C(=O)C(=O)N([Si](C)(C)C)C2=CC([N+](=O)[O-])=C([N+](=O)[O-])C=C21	2587.2	Semi standard non polar	33892256
6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione,2TMS,isomer #1	C[Si](C)(C)N1C(=O)C(=O)N([Si](C)(C)C)C2=CC([N+](=O)[O-])=C([N+](=O)[O-])C=C21	2507.5	Standard non polar	33892256
6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione,2TMS,isomer #1	C[Si](C)(C)N1C(=O)C(=O)N([Si](C)(C)C)C2=CC([N+](=O)[O-])=C([N+](=O)[O-])C=C21	2975.8	Standard polar	33892256
6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C(=O)[NH]C2=CC([N+](=O)[O-])=C([N+](=O)[O-])C=C21	2621.8	Semi standard non polar	33892256
6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C(=O)[NH]C2=CC([N+](=O)[O-])=C([N+](=O)[O-])C=C21	2560.5	Standard non polar	33892256
6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C(=O)[NH]C2=CC([N+](=O)[O-])=C([N+](=O)[O-])C=C21	3356.3	Standard polar	33892256
6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC([N+](=O)[O-])=C([N+](=O)[O-])C=C21	2951.9	Semi standard non polar	33892256
6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC([N+](=O)[O-])=C([N+](=O)[O-])C=C21	2960.6	Standard non polar	33892256
6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC([N+](=O)[O-])=C([N+](=O)[O-])C=C21	3052.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zir-3690000000-40b8e9ba78dcb1d56b63	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione 10V, Positive-QTOF	splash10-0udi-0090000000-5e9e8d621ad7ab564cdb	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione 20V, Positive-QTOF	splash10-000t-0090000000-1edc2220041f5175d011	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione 40V, Positive-QTOF	splash10-008d-0960000000-00931075570886be9b98	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione 10V, Negative-QTOF	splash10-0udi-1090000000-460f0f2f0e63d44d19f9	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione 20V, Negative-QTOF	splash10-0udi-1090000000-e7b0bfe9bef6e7b509c9	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione 40V, Negative-QTOF	splash10-0006-9160000000-3f5f68a8f5724951dfc3	2017-07-26	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB03759

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3899541

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione (HMDB0251552)

MOL for HMDB0251552 (6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione)

3D MOL for HMDB0251552 (6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione)

3D SDF for HMDB0251552 (6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione)

3D-SDF for HMDB0251552 (6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione)

PDB for HMDB0251552 (6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione)

3D PDB for HMDB0251552 (6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione)

SMILES for HMDB0251552 (6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione)

INCHI for HMDB0251552 (6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione)

Structure for HMDB0251552 (6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione)

3D Structure for HMDB0251552 (6,7-Dinitro-1,4-dihydroquinoxaline-2,3-dione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra