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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:27:11 UTC

Update Date

2021-09-26 23:05:11 UTC

HMDB ID

HMDB0252536

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Furagin

Description

Furagin, also known as furazidin or akritoin, belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4. Based on a literature review a significant number of articles have been published on Furagin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Furagin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Furagin 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


  Mrv1652309112112272D          

 19 20  0  0  0  0            999 V2000
    1.3297   -4.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0747   -5.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5597   -5.7376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2497   -5.0702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0052   -4.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7898   -4.0306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6622   -3.8006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6622   -2.9756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3767   -2.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3767   -1.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912   -1.3256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912   -0.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4237   -0.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6787    0.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5037    0.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7586   -0.0157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9886    1.4363    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.6530    2.1900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8091    1.3501    0.0000 O   0  5  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  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  1  7  1  0  0  0  0
  8  7  1  4  0  0  0
  8  9  2  0  0  0  0
 10  9  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
M  CHG  2  17   1  19  -1
M  END
> <DATABASE_ID>
HMDB0252536

> <DATABASE_NAME>
hmdb

> <SMILES>
[O-][N+](=O)C1=CC=C(O1)C=CC=NN1CC(=O)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H8N4O5/c15-8-6-13(10(16)12-8)11-5-1-2-7-3-4-9(19-7)14(17)18/h1-5H,6H2,(H,12,15,16)

> <INCHI_KEY>
DECBQELQORZLLP-UHFFFAOYSA-N

> <FORMULA>
C10H8N4O5

> <MOLECULAR_WEIGHT>
264.197

> <EXACT_MASS>
264.049469374

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
24.089929468197244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{[3-(5-nitrofuran-2-yl)prop-2-en-1-ylidene]amino}imidazolidine-2,4-dione

> <ALOGPS_LOGP>
0.60

> <JCHEM_LOGP>
0.0702718546666666

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.733685553575967

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.233701214690921

> <JCHEM_PKA_STRONGEST_BASIC>
0.4823794487383049

> <JCHEM_POLAR_SURFACE_AREA>
118.05000000000001

> <JCHEM_REFRACTIVITY>
61.602399999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-{[3-(5-nitrofuran-2-yl)prop-2-en-1-ylidene]amino}imidazolidine-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       2.482  -8.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.006  -9.464   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.911 -10.710   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       0.466  -9.464   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -0.010  -8.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.474  -7.524   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       1.236  -7.095   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       1.236  -5.555   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.570  -4.785   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.570  -3.245   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.904  -2.475   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.904  -0.935   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.658  -0.029   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.134   1.435   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.674   1.435   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.149  -0.029   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       5.579   2.681   0.000  0.00  0.00           N+1
HETATM   18  O   UNK     0       4.952   4.088   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.110   2.520   0.000  0.00  0.00           O-1
CONECT    1    2    7                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    1    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15   12                                                       
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0252536
HETATM    1  O1  UNL     1      -3.046   2.034   2.385  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.193   0.918   1.793  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.876   0.669   0.489  1.00  0.00           C  
HETATM    4  N1  UNL     1      -3.044  -0.403  -0.059  1.00  0.00           N  
HETATM    5  N2  UNL     1      -2.708  -0.600  -1.402  1.00  0.00           N  
HETATM    6  C3  UNL     1      -1.490  -0.565  -1.817  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.377  -0.317  -0.914  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.873  -0.282  -1.351  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.000  -0.037  -0.472  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.935   0.186   0.891  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.233   0.369   1.314  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.030   0.250   0.199  1.00  0.00           C  
HETATM   13  N3  UNL     1       5.442   0.363   0.144  1.00  0.00           N1+
HETATM   14  O2  UNL     1       6.132   0.592   1.155  1.00  0.00           O  
HETATM   15  O3  UNL     1       6.101   0.219  -1.051  1.00  0.00           O1-
HETATM   16  O4  UNL     1       3.247   0.011  -0.822  1.00  0.00           O  
HETATM   17  C10 UNL     1      -2.650  -1.202   1.069  1.00  0.00           C  
HETATM   18  O5  UNL     1      -2.293  -2.408   1.014  1.00  0.00           O  
HETATM   19  N4  UNL     1      -2.747  -0.366   2.217  1.00  0.00           N  
HETATM   20  H1  UNL     1      -4.883   0.200   0.644  1.00  0.00           H  
HETATM   21  H2  UNL     1      -3.920   1.546  -0.153  1.00  0.00           H  
HETATM   22  H3  UNL     1      -1.286  -0.722  -2.856  1.00  0.00           H  
HETATM   23  H4  UNL     1      -0.618  -0.161   0.138  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.048  -0.443  -2.399  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.045   0.209   1.487  1.00  0.00           H  
HETATM   26  H7  UNL     1       3.577   0.566   2.313  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.533  -0.629   3.215  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   19
CONECT    3    4   20   21
CONECT    4    5   17
CONECT    5    6    6
CONECT    6    7   22
CONECT    7    8    8   23
CONECT    8    9   24
CONECT    9   10   10   16
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   13   16
CONECT   13   14   14   15
CONECT   17   18   18   19
CONECT   19   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-((3-(5-Nitro-2-furyl)allylidene)amino)-hydantoin	ChEBI
Akritoin	ChEBI
Furazidin	ChEBI
Furazidine	ChEBI
NF 416	ChEBI
NF-416	ChEBI
NF416	ChEBI
Solafur	MeSH

Chemical Formula

C₁₀H₈N₄O₅

Average Molecular Weight

264.197

Monoisotopic Molecular Weight

264.049469374

IUPAC Name

1-{[3-(5-nitrofuran-2-yl)prop-2-en-1-ylidene]amino}imidazolidine-2,4-dione

Traditional Name

1-{[3-(5-nitrofuran-2-yl)prop-2-en-1-ylidene]amino}imidazolidine-2,4-dione

CAS Registry Number

Not Available

SMILES

[O-][N+](=O)C1=CC=C(O1)C=CC=NN1CC(=O)NC1=O

InChI Identifier

InChI=1S/C10H8N4O5/c15-8-6-13(10(16)12-8)11-5-1-2-7-3-4-9(19-7)14(17)18/h1-5H,6H2,(H,12,15,16)

InChI Key

DECBQELQORZLLP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Imidazolidines

Direct Parent

Hydantoins

Alternative Parents

Substituents

Hydantoin
Alpha-amino acid or derivatives
Nitroaromatic compound
2-nitrofuran
Semicarbazone
Dicarboximide
Furan
Heteroaromatic compound
Semicarbazide
C-nitro compound
Carbonic acid derivative
N-alkylated hydrazone
Organic nitro compound
Carboxylic acid derivative
Organic 1,3-dipolar compound
Azacycle
Oxacycle
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxoazanium
Organic zwitterion
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	0.6	ALOGPS
logP	0.07	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.23	ChemAxon
pKa (Strongest Basic)	0.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	118.05 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	61.6 m³·mol⁻¹	ChemAxon
Polarizability	24.09 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]+	154.625	30932474
DeepCCS	[M-H]-	152.229	30932474
DeepCCS	[M-2H]-	185.444	30932474
DeepCCS	[M+Na]+	160.537	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Furagin	[O-][N+](=O)C1=CC=C(O1)C=CC=NN1CC(=O)NC1=O	3648.6	Standard polar	33892256
Furagin	[O-][N+](=O)C1=CC=C(O1)C=CC=NN1CC(=O)NC1=O	2536.4	Standard non polar	33892256
Furagin	[O-][N+](=O)C1=CC=C(O1)C=CC=NN1CC(=O)NC1=O	2786.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Furagin,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CN(N=CC=CC2=CC=C([N+](=O)[O-])O2)C1=O	2682.9	Semi standard non polar	33892256
Furagin,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CN(N=CC=CC2=CC=C([N+](=O)[O-])O2)C1=O	2606.5	Standard non polar	33892256
Furagin,1TMS,isomer #1	C[Si](C)(C)N1C(=O)CN(N=CC=CC2=CC=C([N+](=O)[O-])O2)C1=O	4112.7	Standard polar	33892256
Furagin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CN(N=CC=CC2=CC=C([N+](=O)[O-])O2)C1=O	2959.9	Semi standard non polar	33892256
Furagin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CN(N=CC=CC2=CC=C([N+](=O)[O-])O2)C1=O	2816.1	Standard non polar	33892256
Furagin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)CN(N=CC=CC2=CC=C([N+](=O)[O-])O2)C1=O	4045.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Furagin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9760000000-8e39daff250579303596	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Furagin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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

129387

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146690

PDB ID

Not Available

ChEBI ID

131714

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 Furagin (HMDB0252536)

MOL for HMDB0252536 (Furagin)

3D MOL for HMDB0252536 (Furagin)

3D SDF for HMDB0252536 (Furagin)

3D-SDF for HMDB0252536 (Furagin)

PDB for HMDB0252536 (Furagin)

3D PDB for HMDB0252536 (Furagin)

SMILES for HMDB0252536 (Furagin)

INCHI for HMDB0252536 (Furagin)

Structure for HMDB0252536 (Furagin)

3D Structure for HMDB0252536 (Furagin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra