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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 21:20:32 UTC
Update Date2021-09-26 22:51:43 UTC
HMDB IDHMDB0244158
Secondary Accession NumbersNone
Metabolite Identification
Common Name1,3-Bis(4-nitrophenyl)urea
Description1,3-Bis(4-nitrophenyl)urea, also known as 4,4-DNC or 4,4'-dinitrocarbanilide, belongs to the class of organic compounds known as n-phenylureas. N-phenylureas are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of a urea group. Based on a literature review a small amount of articles have been published on 1,3-Bis(4-nitrophenyl)urea. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1,3-bis(4-nitrophenyl)urea is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1,3-Bis(4-nitrophenyl)urea 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
Thumb
Synonyms
ValueSource
N,N'-bis(4-nitrophenyl)ureaHMDB
4,4-DNCHMDB
4,4'-DinitrocarbanilideHMDB
Chemical FormulaC13H10N4O5
Average Molecular Weight302.246
Monoisotopic Molecular Weight302.065119438
IUPAC Name1,3-bis(4-nitrophenyl)urea
Traditional Nameurea, N,N'-bis(4-nitrophenyl)-
CAS Registry NumberNot Available
SMILES
O=C(NC1=CC=C(C=C1)N(=O)=O)NC1=CC=C(C=C1)N(=O)=O
InChI Identifier
InChI=1S/C13H10N4O5/c18-13(14-9-1-5-11(6-2-9)16(19)20)15-10-3-7-12(8-4-10)17(21)22/h1-8H,(H2,14,15,18)
InChI KeyJEZZOKXIXNSKQD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-phenylureas. N-phenylureas are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of a urea group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassN-phenylureas
Direct ParentN-phenylureas
Alternative Parents
Substituents
  • N-phenylurea
  • Nitrobenzene
  • Nitroaromatic compound
  • C-nitro compound
  • Carbonic acid derivative
  • Urea
  • Organic nitro compound
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.48ALOGPS
logP3ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)10.99ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area132.77 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity80.7 m³·mol⁻¹ChemAxon
Polarizability28.24 ųChemAxon
Number of Rings2ChemAxon
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]+170.52630932474
DeepCCS[M-H]-168.16830932474
DeepCCS[M-2H]-201.12330932474
DeepCCS[M+Na]+176.61930932474
AllCCS[M+H]+165.332859911
AllCCS[M+H-H2O]+161.932859911
AllCCS[M+NH4]+168.432859911
AllCCS[M+Na]+169.232859911
AllCCS[M-H]-166.432859911
AllCCS[M+Na-2H]-165.432859911
AllCCS[M+HCOO]-164.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,3-Bis(4-nitrophenyl)ureaO=C(NC1=CC=C(C=C1)N(=O)=O)NC1=CC=C(C=C1)N(=O)=O4183.9Standard polar33892256
1,3-Bis(4-nitrophenyl)ureaO=C(NC1=CC=C(C=C1)N(=O)=O)NC1=CC=C(C=C1)N(=O)=O3111.8Standard non polar33892256
1,3-Bis(4-nitrophenyl)ureaO=C(NC1=CC=C(C=C1)N(=O)=O)NC1=CC=C(C=C1)N(=O)=O3380.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1,3-Bis(4-nitrophenyl)urea,1TMS,isomer #1C[Si](C)(C)N(C(=O)NC1=CC=C([N+](=O)[O-])C=C1)C1=CC=C([N+](=O)[O-])C=C13125.9Semi standard non polar33892256
1,3-Bis(4-nitrophenyl)urea,1TMS,isomer #1C[Si](C)(C)N(C(=O)NC1=CC=C([N+](=O)[O-])C=C1)C1=CC=C([N+](=O)[O-])C=C12881.6Standard non polar33892256
1,3-Bis(4-nitrophenyl)urea,1TMS,isomer #1C[Si](C)(C)N(C(=O)NC1=CC=C([N+](=O)[O-])C=C1)C1=CC=C([N+](=O)[O-])C=C14003.0Standard polar33892256
1,3-Bis(4-nitrophenyl)urea,2TMS,isomer #1C[Si](C)(C)N(C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C)C1=CC=C([N+](=O)[O-])C=C12866.8Semi standard non polar33892256
1,3-Bis(4-nitrophenyl)urea,2TMS,isomer #1C[Si](C)(C)N(C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C)C1=CC=C([N+](=O)[O-])C=C12824.0Standard non polar33892256
1,3-Bis(4-nitrophenyl)urea,2TMS,isomer #1C[Si](C)(C)N(C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C)C1=CC=C([N+](=O)[O-])C=C13547.9Standard polar33892256
1,3-Bis(4-nitrophenyl)urea,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)NC1=CC=C([N+](=O)[O-])C=C1)C1=CC=C([N+](=O)[O-])C=C13497.8Semi standard non polar33892256
1,3-Bis(4-nitrophenyl)urea,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)NC1=CC=C([N+](=O)[O-])C=C1)C1=CC=C([N+](=O)[O-])C=C13064.1Standard non polar33892256
1,3-Bis(4-nitrophenyl)urea,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)NC1=CC=C([N+](=O)[O-])C=C1)C1=CC=C([N+](=O)[O-])C=C13949.3Standard polar33892256
1,3-Bis(4-nitrophenyl)urea,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C(C)(C)C)C1=CC=C([N+](=O)[O-])C=C13544.5Semi standard non polar33892256
1,3-Bis(4-nitrophenyl)urea,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C(C)(C)C)C1=CC=C([N+](=O)[O-])C=C13216.8Standard non polar33892256
1,3-Bis(4-nitrophenyl)urea,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C(C)(C)C)C1=CC=C([N+](=O)[O-])C=C13563.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1,3-Bis(4-nitrophenyl)urea GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-5901000000-7a78a0dfb08ca55ec2db2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,3-Bis(4-nitrophenyl)urea GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Bis(4-nitrophenyl)urea 10V, Positive-QTOFsplash10-0udi-0009000000-67304ebc09ba8b940ddc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Bis(4-nitrophenyl)urea 20V, Positive-QTOFsplash10-0udr-0059000000-43ba693b3478b975dede2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Bis(4-nitrophenyl)urea 40V, Positive-QTOFsplash10-0uds-1935000000-1595a3eaa8c6b573a55e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Bis(4-nitrophenyl)urea 10V, Negative-QTOFsplash10-0udi-0009000000-30aaab4c306a79c55ff72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Bis(4-nitrophenyl)urea 20V, Negative-QTOFsplash10-0udi-0009000000-22a5325e86b9b55d72262016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Bis(4-nitrophenyl)urea 40V, Negative-QTOFsplash10-0f6y-3902000000-5d06ba13a1db025e754d2016-08-03Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9137
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9509
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]