Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 11:09:41 UTC
Update Date2021-09-26 23:05:57 UTC
HMDB IDHMDB0252995
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Chloro-5-nitro-N-phenylbenzamide
Description2-chloro-5-nitro-N-phenylbenzamide belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group. 2-chloro-5-nitro-N-phenylbenzamide is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). 2-chloro-5-nitro-n-phenylbenzamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2-Chloro-5-nitro-N-phenylbenzamide 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
2-Chloro-5-nitrobenzanilideKegg
2-Chloro-5-nitro-N-phenylbenzene-1-carboximidateGenerator
Chemical FormulaC13H9ClN2O3
Average Molecular Weight276.675
Monoisotopic Molecular Weight276.030169871
IUPAC Name2-chloro-5-nitro-N-phenylbenzamide
Traditional Name2-chloro-5-nitrobenzanilide
CAS Registry NumberNot Available
SMILES
[O-][N+](=O)C1=CC=C(Cl)C(=C1)C(=O)NC1=CC=CC=C1
InChI Identifier
InChI=1S/C13H9ClN2O3/c14-12-7-6-10(16(18)19)8-11(12)13(17)15-9-4-2-1-3-5-9/h1-8H,(H,15,17)
InChI KeyDNTSIBUQMRRYIU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNitrobenzenes
Direct ParentNitrobenzenes
Alternative Parents
Substituents
  • Nitrobenzene
  • Nitroaromatic compound
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • C-nitro compound
  • Organic nitro compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Organic oxoazanium
  • Organic nitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic zwitterion
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
logP3.39ALOGPS
logP3.61ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)11.31ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity73.72 m³·mol⁻¹ChemAxon
Polarizability26.14 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]+156.78230932474
DeepCCS[M-H]-154.38630932474
DeepCCS[M-2H]-188.06430932474
DeepCCS[M+Na]+163.13230932474
AllCCS[M+H]+158.332859911
AllCCS[M+H-H2O]+154.632859911
AllCCS[M+NH4]+161.732859911
AllCCS[M+Na]+162.732859911
AllCCS[M-H]-156.232859911
AllCCS[M+Na-2H]-155.532859911
AllCCS[M+HCOO]-154.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Chloro-5-nitro-N-phenylbenzamide[O-][N+](=O)C1=CC=C(Cl)C(=C1)C(=O)NC1=CC=CC=C13709.3Standard polar33892256
2-Chloro-5-nitro-N-phenylbenzamide[O-][N+](=O)C1=CC=C(Cl)C(=C1)C(=O)NC1=CC=CC=C12441.9Standard non polar33892256
2-Chloro-5-nitro-N-phenylbenzamide[O-][N+](=O)C1=CC=C(Cl)C(=C1)C(=O)NC1=CC=CC=C12470.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Chloro-5-nitro-N-phenylbenzamide,1TMS,isomer #1C[Si](C)(C)N(C(=O)C1=CC([N+](=O)[O-])=CC=C1Cl)C1=CC=CC=C12306.8Semi standard non polar33892256
2-Chloro-5-nitro-N-phenylbenzamide,1TMS,isomer #1C[Si](C)(C)N(C(=O)C1=CC([N+](=O)[O-])=CC=C1Cl)C1=CC=CC=C12339.2Standard non polar33892256
2-Chloro-5-nitro-N-phenylbenzamide,1TMS,isomer #1C[Si](C)(C)N(C(=O)C1=CC([N+](=O)[O-])=CC=C1Cl)C1=CC=CC=C13069.4Standard polar33892256
2-Chloro-5-nitro-N-phenylbenzamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)C1=CC([N+](=O)[O-])=CC=C1Cl)C1=CC=CC=C12579.4Semi standard non polar33892256
2-Chloro-5-nitro-N-phenylbenzamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)C1=CC([N+](=O)[O-])=CC=C1Cl)C1=CC=CC=C12527.9Standard non polar33892256
2-Chloro-5-nitro-N-phenylbenzamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)C1=CC([N+](=O)[O-])=CC=C1Cl)C1=CC=CC=C13122.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fr-9340000000-dcec9154f7dde8c70a032021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide LC-ESI-qTof , Positive-QTOFsplash10-00dj-3960000000-a7dc9d06200fd3114dc22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide , positive-QTOFsplash10-0a4i-3930000000-98176efec89b70f91a6c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 15V, Negative-QTOFsplash10-0a4i-0910000000-8be5c84ea794d6ed15a02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 30V, Negative-QTOFsplash10-0a4i-0900000000-7dfd29352a5856b03c622021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 60V, Negative-QTOFsplash10-0a4i-1900000000-e6cce40ef76ff4d6ab012021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 45V, Negative-QTOFsplash10-0a4i-0900000000-57ae4308b3ba8e03107e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 10V, Positive-QTOFsplash10-004i-0090000000-5028a8df8f9b81c939172016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 20V, Positive-QTOFsplash10-004i-0090000000-60da5ea2b61310aaf7002016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 40V, Positive-QTOFsplash10-004i-3790000000-23e99fa001a60441a6262016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 10V, Negative-QTOFsplash10-004i-0090000000-39fedeb9a2a6430d9b902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 20V, Negative-QTOFsplash10-004i-0090000000-dffc08dc66c339eafabd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 40V, Negative-QTOFsplash10-004l-5290000000-6304f208af68870bab322016-08-03Wishart 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 IDDB07863
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC15627
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound644213
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 ]