Pyrrolnitrin (CED0008004)

Record Information
Version1.0
Creation Date2016-05-22 06:00:57 UTC
Update Date2026-08-18 03:54:35 UTC
Accession NumberCHEM019316
Identification
Common NamePyrrolnitrin
ClassSmall Molecule
Description
Pyrrolnitrin is an organoheterocyclic compound with the formula C10H6Cl2N2O2 and an average molecular weight of 257.07 g/mol. Pyrrolnitrin belongs to the substituted pyrroles, a subclass of pyrroles within the organic compounds. This compound is found in or released from three recorded sources: tobacco smoke filters used in household cleaning and consumer products, the preparation of malt in food, food processing and cookware, and antibiotics within healthcare, pharmaceuticals and veterinary products. Recorded exposure routes for pyrrolnitrin include oral and inhalation.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Chloro-4-(2'-nitro-3'-chlorophenyl)pyrroleChEBI
3-Chloro-4-(3-chloro-2-nitrophenyl)pyrroleChEBI
NSC 107654ChEBI
NSC-107654ChEBI
PirrolnitrinaChEBI
PyrrolnitrineChEBI
PyrrolnitrinumChEBI
Chemical FormulaC10H6Cl2N2O2
Average Molecular Mass257.070 g/mol
Monoisotopic Mass255.981 g/mol
CAS Registry Number1018-71-9
IUPAC Name3-chloro-4-(3-chloro-2-nitrophenyl)-1H-pyrrole
Traditional Namepyrrolnitrin
SMILES[O-][N+](=O)C1=C(Cl)C=CC=C1C1=CNC=C1Cl
InChI IdentifierInChI=1S/C10H6Cl2N2O2/c11-8-3-1-2-6(10(8)14(15)16)7-4-13-5-9(7)12/h1-5,13H
InChI KeyQJBZDBLBQWFTPZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrroles
Sub ClassSubstituted pyrroles
Direct ParentPhenylpyrroles
Alternative Parents
Substituents
  • 3-phenylpyrrole
  • Nitrobenzene
  • Nitroaromatic compound
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Organic nitro compound
  • C-nitro compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Azacycle
  • Organic oxoazanium
  • Organic 1,3-dipolar compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.072 g/LALOGPS
logP3.86ALOGPS
logP3.85ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)15.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area58.93 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity61.88 m³·mol⁻¹ChemAxon
Polarizability22.54 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0090000000-f6ad5cd4ead742601b39Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-9c7ee7a00096ebc769adNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0znc-0290000000-f8128d718262b7d8e34eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-be486096da708c149e42Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-30c7238a5418140123e7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uyu-2790000000-8e241ce25ed4df3902a2Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
574.0Log mg/kg[320:1000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
642FootwearTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Toll-like receptor 9 structureClick to view 3D structureToll-like receptor 9Q9NR96HumansPredicted (SEA)50.2906
Click to view 3D structureProtein RecAP9WHJ3Mycobacterium tuberculosisPredicted (SEA)242.189
Click to view 3D structureNucleoproteinP15682Influenza A virus (strain A/Wilson-Smith/1933 H1N1)Predicted (SEA)23.6662
Fatty acid synthase structureClick to view 3D structureFatty acid synthaseP49327HumansPredicted (SEA)288.821
Click to view 3D structureSH3 and multiple ankyrin repeat domains protein 3Q4ACU6Mus musculusPredicted (SEA)0.778492
Click to view 3D structureHeat shock factor protein 1P38532Mus musculusPredicted (SEA)651.131
G-protein coupled receptor 55 structureClick to view 3D structureG-protein coupled receptor 55Q9Y2T6HumansPredicted (SEA)400.301
Click to view 3D structureBeta LactamaseQ932Y6Pseudomonas aeruginosaPredicted (SEA)293.024
Kappa-type opioid receptor structureClick to view 3D structureKappa-type opioid receptorP41145HumansPredicted (SEA)2589.65
Protein S100-A4 structureClick to view 3D structureProtein S100-A4P26447HumansPredicted (SEA)12.4559
Click to view 3D structureDNA damage-inducible transcript 3 proteinP35639Mus musculusPredicted (SEA)1294.79
X-box-binding protein 1 structureClick to view 3D structureX-box-binding protein 1P17861HumansPredicted (SEA)1296.89
Endolysin structureClick to view 3D structureEndolysinP00720Enterobacteria phage T4Predicted (SEA)40.5594
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)4998.7
Type-1 angiotensin II receptor structureClick to view 3D structureType-1 angiotensin II receptorP30556HumansPredicted (SEA)1181.21
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)5786.07
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)4796.06
Arylsulfatase structureClick to view 3D structureArylsulfataseP51691Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)Predicted (SEA)35.4992
Click to view 3D structureNH(3)-dependent NAD(+) synthetaseQ81RP3Bacillus anthracisPredicted (SEA)91.3171
Click to view 3D structurePoly(ADP-ribose) glycohydrolaseI6L8L7Tetrahymena thermophilaPredicted (SEA)16.6597
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)5197.84
Proto-oncogene tyrosine-protein kinase Src structureClick to view 3D structureProto-oncogene tyrosine-protein kinase SrcP12931HumansPredicted (SEA)4877.88
Focal adhesion kinase 1 structureClick to view 3D structureFocal adhesion kinase 1Q05397HumansPredicted (SEA)4047.23
Transthyretin structureClick to view 3D structureTransthyretinP02766HumansPredicted (SEA)275.197
Aldo-keto reductase family 1 member C3 structureClick to view 3D structureAldo-keto reductase family 1 member C3P42330HumansPredicted (SEA)784.876
Concentrations
Not Available
External Links
DrugBank IDDB13603
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00018726
BiGG IDNot Available
BioCyc IDCPD-12776
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPyrrolnitrin
Chemspider IDNot Available
ChEBI ID32079
PubChem Compound ID13916
Kegg Compound IDC12491
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23149469
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23990066
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25679537
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=25901993
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=4379208
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=4955234