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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2023-02-21 17:18:10 UTC
HMDB IDHMDB0014480
Secondary Accession Numbers
  • HMDB14480
Metabolite Identification
Common NameNitrofurazone
DescriptionNitrofurazone is only found in individuals that have used or taken this drug. It is a topical anti-infective agent effective against gram-negative and gram-positive bacteria. It is used for superficial wounds, burns, ulcers, and skin infections. Nitrofurazone has also been administered orally in the treatment of trypanosomiasis. [PubChem]The exact mechanism of action is unknown. Nitrofurazone inhibits several bacterial enzymes, especially those involved in the aerobic and anaerobic degradation of glucose and pyruvate. This activity is believed also to affect pyruvate dehydrogenase, citrate synthetase, malate dehydrogenase, glutathione reductase, and pyruvate decarboxylase.
Structure
Data?1676999890
Synonyms
ValueSource
5-Nitro-2-furaldehyde semicarbazoneKegg
NitrofuralKegg
FuracinKegg
NFZHMDB
NitrofurazanHMDB
FuracilinHMDB
FuracillinHMDB
Nitrofurazone, calcium (2:1) saltHMDB
Chemical FormulaC6H6N4O4
Average Molecular Weight198.1362
Monoisotopic Molecular Weight198.0389047
IUPAC Name[(E)-[(5-nitrofuran-2-yl)methylidene]amino]urea
Traditional Namenitrofurazone
CAS Registry Number59-87-0
SMILES
NC(=O)N\N=C\C1=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)/b8-3+
InChI KeyIAIWVQXQOWNYOU-FPYGCLRLSA-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFurans
Sub ClassNitrofurans
Direct ParentNitrofurans
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 FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point238 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.27 g/LNot Available
LogP0.2Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available138.628http://allccs.zhulab.cn/database/detail?ID=AllCCS00001008
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.27 g/LALOGPS
logP0.23ALOGPS
logP-0.14ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)11.79ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area126.44 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.21 m³·mol⁻¹ChemAxon
Polarizability16.92 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+133.76230932474
DeepCCS[M-H]-130.50230932474
DeepCCS[M-2H]-166.32130932474
DeepCCS[M+Na]+142.05930932474
AllCCS[M+H]+141.132859911
AllCCS[M+H-H2O]+137.132859911
AllCCS[M+NH4]+144.932859911
AllCCS[M+Na]+145.932859911
AllCCS[M-H]-138.432859911
AllCCS[M+Na-2H]-138.932859911
AllCCS[M+HCOO]-139.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NitrofurazoneNC(=O)N\N=C\C1=CC=C(O1)[N+]([O-])=O2295.9Standard polar33892256
NitrofurazoneNC(=O)N\N=C\C1=CC=C(O1)[N+]([O-])=O1968.8Standard non polar33892256
NitrofurazoneNC(=O)N\N=C\C1=CC=C(O1)[N+]([O-])=O2127.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Nitrofurazone,1TMS,isomer #1C[Si](C)(C)NC(=O)N/N=C/C1=CC=C([N+](=O)[O-])O12196.7Semi standard non polar33892256
Nitrofurazone,1TMS,isomer #1C[Si](C)(C)NC(=O)N/N=C/C1=CC=C([N+](=O)[O-])O12172.5Standard non polar33892256
Nitrofurazone,1TMS,isomer #1C[Si](C)(C)NC(=O)N/N=C/C1=CC=C([N+](=O)[O-])O13638.2Standard polar33892256
Nitrofurazone,1TMS,isomer #2C[Si](C)(C)N(/N=C/C1=CC=C([N+](=O)[O-])O1)C(N)=O2145.6Semi standard non polar33892256
Nitrofurazone,1TMS,isomer #2C[Si](C)(C)N(/N=C/C1=CC=C([N+](=O)[O-])O1)C(N)=O2070.1Standard non polar33892256
Nitrofurazone,1TMS,isomer #2C[Si](C)(C)N(/N=C/C1=CC=C([N+](=O)[O-])O1)C(N)=O3646.4Standard polar33892256
Nitrofurazone,2TMS,isomer #1C[Si](C)(C)N(C(=O)N/N=C/C1=CC=C([N+](=O)[O-])O1)[Si](C)(C)C2240.1Semi standard non polar33892256
Nitrofurazone,2TMS,isomer #1C[Si](C)(C)N(C(=O)N/N=C/C1=CC=C([N+](=O)[O-])O1)[Si](C)(C)C2255.6Standard non polar33892256
Nitrofurazone,2TMS,isomer #1C[Si](C)(C)N(C(=O)N/N=C/C1=CC=C([N+](=O)[O-])O1)[Si](C)(C)C3149.9Standard polar33892256
Nitrofurazone,2TMS,isomer #2C[Si](C)(C)NC(=O)N(/N=C/C1=CC=C([N+](=O)[O-])O1)[Si](C)(C)C2187.1Semi standard non polar33892256
Nitrofurazone,2TMS,isomer #2C[Si](C)(C)NC(=O)N(/N=C/C1=CC=C([N+](=O)[O-])O1)[Si](C)(C)C2212.6Standard non polar33892256
Nitrofurazone,2TMS,isomer #2C[Si](C)(C)NC(=O)N(/N=C/C1=CC=C([N+](=O)[O-])O1)[Si](C)(C)C3134.2Standard polar33892256
Nitrofurazone,3TMS,isomer #1C[Si](C)(C)N(/N=C/C1=CC=C([N+](=O)[O-])O1)C(=O)N([Si](C)(C)C)[Si](C)(C)C2217.5Semi standard non polar33892256
Nitrofurazone,3TMS,isomer #1C[Si](C)(C)N(/N=C/C1=CC=C([N+](=O)[O-])O1)C(=O)N([Si](C)(C)C)[Si](C)(C)C2317.0Standard non polar33892256
Nitrofurazone,3TMS,isomer #1C[Si](C)(C)N(/N=C/C1=CC=C([N+](=O)[O-])O1)C(=O)N([Si](C)(C)C)[Si](C)(C)C2678.4Standard polar33892256
Nitrofurazone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)N/N=C/C1=CC=C([N+](=O)[O-])O12452.2Semi standard non polar33892256
Nitrofurazone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)N/N=C/C1=CC=C([N+](=O)[O-])O12345.5Standard non polar33892256
Nitrofurazone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)N/N=C/C1=CC=C([N+](=O)[O-])O13556.8Standard polar33892256
Nitrofurazone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(/N=C/C1=CC=C([N+](=O)[O-])O1)C(N)=O2391.1Semi standard non polar33892256
Nitrofurazone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(/N=C/C1=CC=C([N+](=O)[O-])O1)C(N)=O2256.7Standard non polar33892256
Nitrofurazone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(/N=C/C1=CC=C([N+](=O)[O-])O1)C(N)=O3589.8Standard polar33892256
Nitrofurazone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)N/N=C/C1=CC=C([N+](=O)[O-])O1)[Si](C)(C)C(C)(C)C2701.9Semi standard non polar33892256
Nitrofurazone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)N/N=C/C1=CC=C([N+](=O)[O-])O1)[Si](C)(C)C(C)(C)C2646.6Standard non polar33892256
Nitrofurazone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)N/N=C/C1=CC=C([N+](=O)[O-])O1)[Si](C)(C)C(C)(C)C3036.0Standard polar33892256
Nitrofurazone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)N(/N=C/C1=CC=C([N+](=O)[O-])O1)[Si](C)(C)C(C)(C)C2673.6Semi standard non polar33892256
Nitrofurazone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)N(/N=C/C1=CC=C([N+](=O)[O-])O1)[Si](C)(C)C(C)(C)C2615.0Standard non polar33892256
Nitrofurazone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)N(/N=C/C1=CC=C([N+](=O)[O-])O1)[Si](C)(C)C(C)(C)C3054.7Standard polar33892256
Nitrofurazone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(/N=C/C1=CC=C([N+](=O)[O-])O1)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2931.5Semi standard non polar33892256
Nitrofurazone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(/N=C/C1=CC=C([N+](=O)[O-])O1)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2914.8Standard non polar33892256
Nitrofurazone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(/N=C/C1=CC=C([N+](=O)[O-])O1)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2805.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Nitrofurazone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-6900000000-ab197de8a008fa662f842017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nitrofurazone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0pb9-9500000000-c26d5be0126e0a0e82782014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Nitrofurazone 15V, Negative-QTOFsplash10-053r-8900000000-fb74d5d88d31817fc4fb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nitrofurazone 30V, Negative-QTOFsplash10-053r-9700000000-74ab81d6c8af01bd4c9f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nitrofurazone 60V, Negative-QTOFsplash10-05o1-9100000000-3bfaf343549c655346fd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nitrofurazone 45V, Negative-QTOFsplash10-05o1-9300000000-0e1b313ba36c19497a2f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nitrofurazone 30V, Positive-QTOFsplash10-053r-9700000000-b6d6c2a8031086e8b6682021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nitrofurazone 90V, Negative-QTOFsplash10-0002-9000000000-955108ce74e1ade052dc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nitrofurazone 75V, Negative-QTOFsplash10-00nb-9100000000-b1c82af570ca70ff4e2d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrofurazone 10V, Positive-QTOFsplash10-0002-1900000000-1d212d3b29501750343d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrofurazone 20V, Positive-QTOFsplash10-0005-2900000000-92bf34b3a15306ef76e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrofurazone 40V, Positive-QTOFsplash10-076u-9100000000-5e4b72f2b73083a734822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrofurazone 10V, Negative-QTOFsplash10-0002-2900000000-9af17389b9526ffe05772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrofurazone 20V, Negative-QTOFsplash10-0002-9600000000-5ad22b05c4609624cd572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrofurazone 40V, Negative-QTOFsplash10-0f6x-9000000000-e4513cbb2f82a212f5792016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrofurazone 10V, Negative-QTOFsplash10-0002-0900000000-96f86f6fac5c42a704722021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrofurazone 20V, Negative-QTOFsplash10-052g-9200000000-acad3af6af9f29b9a5e62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrofurazone 40V, Negative-QTOFsplash10-0006-9000000000-fbefaa72589c442a13242021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrofurazone 10V, Positive-QTOFsplash10-0002-0900000000-724e2d600be54174b51d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrofurazone 20V, Positive-QTOFsplash10-0a5j-0900000000-c322c50510d759eea8832021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrofurazone 40V, Positive-QTOFsplash10-000i-9300000000-053c8b358b6df0eaa5922021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00336 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00336 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00336
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4566720
KEGG Compound IDC08042
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNitrofural
METLIN IDNot Available
PubChem Compound5447130
PDB IDNFZ
ChEBI ID170239
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular weight:
146422.99
References
  1. Tatsumi K, Kitamura S, Yoshimura H: Reduction of nitrofuran derivatives by xanthine oxidase and microsomes. Isolation and identification of reduction products. Arch Biochem Biophys. 1976 Jul;175(1):131-7. [PubMed:952514 ]
  2. Kutcher WW, McCalla DR: Aerobic reduction of 5-nitro-2-furaldehyde semicarbazone by rat liver xanthine dehydrogenase. Biochem Pharmacol. 1984 Mar 1;33(5):799-805. [PubMed:6585203 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]