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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:11:00 UTC

Update Date

2021-09-26 22:56:41 UTC

HMDB ID

HMDB0247170

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione

Description

(E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione 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. Based on a literature review very few articles have been published on (E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione. This compound has been identified in human blood as reported by (PMID: 31557052 ). (e)-5-(quinoxalin-6-ylmethylene)thiazolidine-2,4-dione is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-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

  Mrv1652309112102112D          

 18 20  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -2.7050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -3.7445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974   -4.4120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -2.9599    0.0000 S   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  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  1 10  1  0  0  0  0
 11 10  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 12 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247170

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1NC(=O)C(S1)=CC1=CC2=NC=CN=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H7N3O2S/c16-11-10(18-12(17)15-11)6-7-1-2-8-9(5-7)14-4-3-13-8/h1-6H,(H,15,16,17)

> <INCHI_KEY>
SQWZFLMPDUSYGV-UHFFFAOYSA-N

> <FORMULA>
C12H7N3O2S

> <MOLECULAR_WEIGHT>
257.27

> <EXACT_MASS>
257.025897651

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
24.853189321134213

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(quinoxalin-6-yl)methylidene]-1,3-thiazolidine-2,4-dione

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
1.175791529

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.902617548961312

> <JCHEM_PKA_STRONGEST_BASIC>
1.6302922609385633

> <JCHEM_POLAR_SURFACE_AREA>
71.95

> <JCHEM_REFRACTIVITY>
67.6134

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(quinoxalin-6-ylmethylidene)-1,3-thiazolidine-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       5.335   0.000   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.246  -5.525   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.711  -5.049   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       0.770  -6.990   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -0.770  -6.990   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.675  -8.236   0.000  0.00  0.00           O+0
HETATM   18  S   UNK     0      -1.246  -5.525   0.000  0.00  0.00           S+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9    1   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0247170
HETATM    1  O1  UNL     1      -4.994   2.415   0.335  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.318   1.360   0.172  1.00  0.00           C  
HETATM    3  N1  UNL     1      -4.778   0.032   0.011  1.00  0.00           N  
HETATM    4  C2  UNL     1      -3.819  -0.948  -0.164  1.00  0.00           C  
HETATM    5  O2  UNL     1      -4.106  -2.189  -0.319  1.00  0.00           O  
HETATM    6  C3  UNL     1      -2.448  -0.518  -0.161  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.336  -1.194  -0.302  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.030  -0.535  -0.269  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.188   0.649  -0.930  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.424   1.253  -0.817  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.415   0.653  -0.047  1.00  0.00           C  
HETATM   12  N2  UNL     1       3.614   1.254   0.075  1.00  0.00           N  
HETATM   13  C9  UNL     1       4.587   0.700   0.830  1.00  0.00           C  
HETATM   14  C10 UNL     1       4.397  -0.490   1.500  1.00  0.00           C  
HETATM   15  N3  UNL     1       3.195  -1.080   1.370  1.00  0.00           N  
HETATM   16  C11 UNL     1       2.197  -0.538   0.613  1.00  0.00           C  
HETATM   17  C12 UNL     1       0.955  -1.133   0.495  1.00  0.00           C  
HETATM   18  S1  UNL     1      -2.528   1.257   0.098  1.00  0.00           S  
HETATM   19  H1  UNL     1      -5.827  -0.150   0.032  1.00  0.00           H  
HETATM   20  H2  UNL     1      -1.360  -2.258  -0.456  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.585   1.074  -1.513  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.592   2.186  -1.340  1.00  0.00           H  
HETATM   23  H5  UNL     1       5.555   1.205   0.919  1.00  0.00           H  
HETATM   24  H6  UNL     1       5.181  -0.943   2.107  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.829  -2.058   1.023  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   18
CONECT    3    4   19
CONECT    4    5    5    6
CONECT    6    7    7   18
CONECT    7    8   20
CONECT    8    9    9   17
CONECT    9   10   21
CONECT   10   11   11   22
CONECT   11   12   16
CONECT   12   13   13
CONECT   13   14   23
CONECT   14   15   15   24
CONECT   15   16
CONECT   16   17   17
CONECT   17   25
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Quinoxalin-6-ylmethylenethiazolidine-2,4-dione	HMDB

Chemical Formula

C₁₂H₇N₃O₂S

Average Molecular Weight

257.27

Monoisotopic Molecular Weight

257.025897651

IUPAC Name

5-[(quinoxalin-6-yl)methylidene]-1,3-thiazolidine-2,4-dione

Traditional Name

5-(quinoxalin-6-ylmethylidene)-1,3-thiazolidine-2,4-dione

CAS Registry Number

Not Available

SMILES

O=C1NC(=O)C(S1)=CC1=CC2=NC=CN=C2C=C1

InChI Identifier

InChI=1S/C12H7N3O2S/c16-11-10(18-12(17)15-11)6-7-1-2-8-9(5-7)14-4-3-13-8/h1-6H,(H,15,16,17)

InChI Key

SQWZFLMPDUSYGV-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
Thiazolidinedione
Pyrazine
Benzenoid
Dicarboximide
Heteroaromatic compound
Thiazolidine
Carbonic acid derivative
Thiocarbamic acid derivative
Carboxylic acid derivative
Azacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen 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	1.17	ALOGPS
logP	1.18	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.9	ChemAxon
pKa (Strongest Basic)	1.63	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.95 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.61 m³·mol⁻¹	ChemAxon
Polarizability	24.85 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	154.312	30932474
DeepCCS	[M-H]-	151.954	30932474
DeepCCS	[M-2H]-	184.881	30932474
DeepCCS	[M+Na]+	160.405	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione,1TMS,isomer #1	C[Si](C)(C)N1C(=O)SC(=CC2=CC=C3N=CC=NC3=C2)C1=O	2867.6	Semi standard non polar	33892256
(E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione,1TMS,isomer #1	C[Si](C)(C)N1C(=O)SC(=CC2=CC=C3N=CC=NC3=C2)C1=O	2606.6	Standard non polar	33892256
(E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione,1TMS,isomer #1	C[Si](C)(C)N1C(=O)SC(=CC2=CC=C3N=CC=NC3=C2)C1=O	3995.0	Standard polar	33892256
(E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)SC(=CC2=CC=C3N=CC=NC3=C2)C1=O	3109.4	Semi standard non polar	33892256
(E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)SC(=CC2=CC=C3N=CC=NC3=C2)C1=O	2860.4	Standard non polar	33892256
(E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)SC(=CC2=CC=C3N=CC=NC3=C2)C1=O	3948.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione GC-MS (Non-derivatized) - 70eV, Positive	splash10-053i-1690000000-bd51c44b101ccccc3cff	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-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 - (E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione 10V, Positive-QTOF	splash10-0a4i-0090000000-12d4229834aa68daccf5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione 20V, Positive-QTOF	splash10-000i-0940000000-debeba997909cbb52866	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione 40V, Positive-QTOF	splash10-0uei-0900000000-0b7763f37ea1fe7252c3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione 10V, Negative-QTOF	splash10-0a4i-0490000000-23935b6e643fef15a0a9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione 20V, Negative-QTOF	splash10-000i-0930000000-5a4ffb6bb63d2528fe76	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione 40V, Negative-QTOF	splash10-000l-5900000000-a113d2fd8c435d1c787d	2021-10-12	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21395321

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24906273

PDB ID

Not Available

ChEBI ID

91356

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 (E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione (HMDB0247170)

MOL for HMDB0247170 ((E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione)

3D MOL for HMDB0247170 ((E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione)

3D SDF for HMDB0247170 ((E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione)

3D-SDF for HMDB0247170 ((E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione)

PDB for HMDB0247170 ((E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione)

3D PDB for HMDB0247170 ((E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione)

SMILES for HMDB0247170 ((E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione)

INCHI for HMDB0247170 ((E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione)

Structure for HMDB0247170 ((E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione)

3D Structure for HMDB0247170 ((E)-5-(Quinoxalin-6-ylmethylene)thiazolidine-2,4-dione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra