MiMeDB: Showing metabocard for nitrofurazone (MMDBc0032862)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 22:03:18 UTC

Update Date

2024-09-29 14:35:35 UTC

Metabolite ID

MMDBc0032862

Metabolite Identification

Common Name

nitrofurazone

Description

A semicarbazone resulting from the formal condensation of semicarbazide with 5-nitrofuraldehyde. A broad spectrum antibacterial drug, although with little activity against Pseudomonas species, it is used as a local application for burns, ulcers, wo

Structure

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


  Mrv1652309112120092D          

 14 14  0  0  0  0            999 V2000
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351   -1.4039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4555   -1.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9405   -1.9851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7911   -0.5640    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  1  0  0  0  0
  4  5  2  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  2  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  CHG  2   6   1   8  -1
M  END
> <DATABASE_ID>
MMDBc0032862

> <DATABASE_NAME>
MIME

> <SMILES>
NC(=O)NN=CC1=CC=C(O1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H6N4O4/c7-6(11)9-8-3-4-1-2-5(14-4)10(12)13/h1-3H,(H3,7,9,11)

> <INCHI_KEY>
IAIWVQXQOWNYOU-UHFFFAOYSA-N

> <FORMULA>
C6H6N4O4

> <MOLECULAR_WEIGHT>
198.138

> <EXACT_MASS>
198.038904689

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
17.100779620871243

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{[(5-nitrofuran-2-yl)methylidene]amino}urea

> <ALOGPS_LOGP>
0.23

> <JCHEM_LOGP>
-0.13506338633333326

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.213885115106688

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.794831274785802

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9815602115668405

> <JCHEM_POLAR_SURFACE_AREA>
123.76

> <JCHEM_REFRACTIVITY>
44.2064

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-nitrofurfural semicarbazone

> <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       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.060   3.620   0.000  0.00  0.00           N+1
HETATM    7  O   UNK     0       2.393   4.390   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -0.274   4.390   0.000  0.00  0.00           O-1
HETATM    9  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -2.147  -1.375   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      -3.052  -2.621   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -4.584  -2.460   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.489  -3.706   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0      -5.210  -1.053   0.000  0.00  0.00           N+0
CONECT    1    2    5                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

Synonyms

Value	Source
(5-Nitro-2-furfurylidenamino)urea	ChEBI
1-(5-Nitro-2-furfurylidene)semicarbazide	ChEBI
5-Nitro-2-furaldehyde semicarbazone	ChEBI
5-Nitrofuraldehyde semicarbazide	ChEBI
5-Nitrofuran-2-carbaldehyde semicarbazone	ChEBI
5-Nitrofurfural semicarbazone	ChEBI
Alfucin	ChEBI
Amifur	ChEBI
Chemofuran	ChEBI
Furacillin	ChEBI
Furacin	ChEBI
Furacinetten	ChEBI
Furacoccid	ChEBI
Furaldon	ChEBI
Furazol W	ChEBI
Furesol	ChEBI
Mammex	ChEBI
Mastofuran	ChEBI
Monafuracin	ChEBI
Nifuzon	ChEBI
Nitrofural	ChEBI
Nitrofuralum	ChEBI

Molecular Formula

C₆H₆N₄O₄

Average Mass

198.138

Monoisotopic Mass

198.038904689

IUPAC Name

{[(5-nitrofuran-2-yl)methylidene]amino}urea

Traditional Name

5-nitrofurfural semicarbazone

CAS Registry Number

Not Available

SMILES

NC(=O)NN=CC1=CC=C(O1)[N+]([O-])=O

InChI Identifier

InChI=1S/C6H6N4O4/c7-6(11)9-8-3-4-1-2-5(14-4)10(12)13/h1-3H,(H3,7,9,11)

InChI Key

IAIWVQXQOWNYOU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrofurans. Nitrofurans are compounds containing a furan ring which bears a nitro group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furans

Sub Class

Nitrofurans

Direct Parent

Nitrofurans

Alternative Parents

Substituents

Nitroaromatic compound
2-nitrofuran
Semicarbazone
Semicarbazide
Heteroaromatic compound
C-nitro compound
Carbonic acid derivative
Organic nitro compound
Organic oxoazanium
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic zwitterion
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

semicarbazone (CHEBI:44368 )
nitrofuran antibiotic (CHEBI:44368 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.27 g/L	ALOGPS
logP	0.23	ALOGPS
logP	-0.14	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	11.79	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	123.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	44.21 m³·mol⁻¹	ChemAxon
Polarizability	17.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-6900000000-ab197de8a008fa662f84	2021-09-24	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-10-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-10-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-10-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-10-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-10-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-10-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-10-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-10-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-10-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-10-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-10-27	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human sputum; Human subgingival plaque; Human feces	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0257247

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

1773

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nitrofural

METLIN ID

Not Available

PubChem Compound

1839

PDB ID

Not Available

ChEBI ID

44368

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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 nitrofurazone (MMDBc0032862)

MOL for #<Metabolite:0x00007f46e4de94a0>

3D MOL for #<Metabolite:0x00007f46e4de94a0>

3D SDF for #<Metabolite:0x00007f46e4de94a0>

3D-SDF for #<Metabolite:0x00007f46e4de94a0>

PDB for #<Metabolite:0x00007f46e4de94a0>

3D PDB for #<Metabolite:0x00007f46e4de94a0>

SMILES for #<Metabolite:0x00007f46e4de94a0>

INCHI for #<Metabolite:0x00007f46e4de94a0>

Structure for #<Metabolite:0x00007f46e4de94a0>

3D Structure for #<Metabolite:0x00007f46e4de94a0>