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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 16:18:44 UTC
Update Date2021-09-26 23:11:26 UTC
HMDB IDHMDB0256055
Secondary Accession NumbersNone
Metabolite Identification
Common Namep-Phenylenediamine
Description1,4-phenylenediamine, also known as PPD or 1,4-diaminobenzene, belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. Based on a literature review a significant number of articles have been published on 1,4-phenylenediamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). P-phenylenediamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically p-Phenylenediamine 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
1,4-BenzenediamineChEBI
1,4-DiaminobenzeneChEBI
4-AminoanilineChEBI
4-PhenylenediamineChEBI
p-DiaminobenzeneChEBI
p-PhenylenediamineChEBI
p-Phenylenediamine baseChEBI
Para-phenylenediamineChEBI
Paraphenylene-diamineChEBI
PPDChEBI
PPDAChEBI
1,4-PhenyldiamineMeSH
1,4-PhenylenediamineMeSH
4-Phenylenediamine bromide, ion(1+)MeSH
4-Phenylenediamine dihydrochlorideMeSH
4-Phenylenediamine diperchlorateMeSH
4-Phenylenediamine ion (1+)MeSH
4-Phenylenediamine monohydrobromideMeSH
4-Phenylenediamine monohydrochlorideMeSH
4-Phenylenediamine monohydroiodideMeSH
4-Phenylenediamine monooxalateMeSH
4-Phenylenediamine monoperchlorateMeSH
4-Phenylenediamine monosulfateMeSH
4-Phenylenediamine sulfateMeSH
Ursol-DMeSH
Black hennaMeSH
ParaphenylenediamineMeSH
Chemical FormulaC6H8N2
Average Molecular Weight108.144
Monoisotopic Molecular Weight108.068748266
IUPAC Namebenzene-1,4-diamine
Traditional Namep-phenylenediamine
CAS Registry NumberNot Available
SMILES
NC1=CC=C(N)C=C1
InChI Identifier
InChI=1S/C6H8N2/c7-5-1-2-6(8)4-3-5/h1-4H,7-8H2
InChI KeyCBCKQZAAMUWICA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAniline and substituted anilines
Direct ParentAniline and substituted anilines
Alternative Parents
Substituents
  • Aniline or substituted anilines
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not 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
logP-0.01ALOGPS
logP0.32ChemAxon
logS-0.15ALOGPS
pKa (Strongest Basic)6.46ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.04 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.46 m³·mol⁻¹ChemAxon
Polarizability11.72 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+125.23630932474
DeepCCS[M-H]-121.89630932474
DeepCCS[M-2H]-158.81530932474
DeepCCS[M+Na]+133.930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
p-PhenylenediamineNC1=CC=C(N)C=C12463.5Standard polar33892256
p-PhenylenediamineNC1=CC=C(N)C=C11252.5Standard non polar33892256
p-PhenylenediamineNC1=CC=C(N)C=C11293.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
p-Phenylenediamine,1TMS,isomer #1C[Si](C)(C)NC1=CC=C(N)C=C11545.3Semi standard non polar33892256
p-Phenylenediamine,1TMS,isomer #1C[Si](C)(C)NC1=CC=C(N)C=C11518.5Standard non polar33892256
p-Phenylenediamine,1TMS,isomer #1C[Si](C)(C)NC1=CC=C(N)C=C12000.7Standard polar33892256
p-Phenylenediamine,2TMS,isomer #1C[Si](C)(C)NC1=CC=C(N[Si](C)(C)C)C=C11711.7Semi standard non polar33892256
p-Phenylenediamine,2TMS,isomer #1C[Si](C)(C)NC1=CC=C(N[Si](C)(C)C)C=C11708.6Standard non polar33892256
p-Phenylenediamine,2TMS,isomer #1C[Si](C)(C)NC1=CC=C(N[Si](C)(C)C)C=C11695.0Standard polar33892256
p-Phenylenediamine,2TMS,isomer #2C[Si](C)(C)N(C1=CC=C(N)C=C1)[Si](C)(C)C1635.7Semi standard non polar33892256
p-Phenylenediamine,2TMS,isomer #2C[Si](C)(C)N(C1=CC=C(N)C=C1)[Si](C)(C)C1653.6Standard non polar33892256
p-Phenylenediamine,2TMS,isomer #2C[Si](C)(C)N(C1=CC=C(N)C=C1)[Si](C)(C)C1930.3Standard polar33892256
p-Phenylenediamine,3TMS,isomer #1C[Si](C)(C)NC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C11725.4Semi standard non polar33892256
p-Phenylenediamine,3TMS,isomer #1C[Si](C)(C)NC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C11735.3Standard non polar33892256
p-Phenylenediamine,3TMS,isomer #1C[Si](C)(C)NC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C11684.4Standard polar33892256
p-Phenylenediamine,4TMS,isomer #1C[Si](C)(C)N(C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C1828.9Semi standard non polar33892256
p-Phenylenediamine,4TMS,isomer #1C[Si](C)(C)N(C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C1848.3Standard non polar33892256
p-Phenylenediamine,4TMS,isomer #1C[Si](C)(C)N(C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C1600.0Standard polar33892256
p-Phenylenediamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(N)C=C11727.4Semi standard non polar33892256
p-Phenylenediamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(N)C=C11698.7Standard non polar33892256
p-Phenylenediamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(N)C=C12115.9Standard polar33892256
p-Phenylenediamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(N[Si](C)(C)C(C)(C)C)C=C12188.6Semi standard non polar33892256
p-Phenylenediamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(N[Si](C)(C)C(C)(C)C)C=C12070.6Standard non polar33892256
p-Phenylenediamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(N[Si](C)(C)C(C)(C)C)C=C11951.5Standard polar33892256
p-Phenylenediamine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=C(N)C=C1)[Si](C)(C)C(C)(C)C2044.8Semi standard non polar33892256
p-Phenylenediamine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=C(N)C=C1)[Si](C)(C)C(C)(C)C2069.0Standard non polar33892256
p-Phenylenediamine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=C(N)C=C1)[Si](C)(C)C(C)(C)C2054.4Standard polar33892256
p-Phenylenediamine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C12467.1Semi standard non polar33892256
p-Phenylenediamine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C12338.6Standard non polar33892256
p-Phenylenediamine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C12051.2Standard polar33892256
p-Phenylenediamine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2712.1Semi standard non polar33892256
p-Phenylenediamine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2625.2Standard non polar33892256
p-Phenylenediamine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2073.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - p-Phenylenediamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-3900000000-61081929d919d712e3352021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Phenylenediamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-e3b4bf12745fc30aecd92014-10-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Phenylenediamine 45V, Positive-QTOFsplash10-0006-9000000000-34661e2d00632dd3d0512021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Phenylenediamine 60V, Positive-QTOFsplash10-0a4i-2900000000-ac88e1845d9bf63df0522021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Phenylenediamine 105V, Positive-QTOFsplash10-052f-9300000000-507544e80b10aab335342021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Phenylenediamine 120V, Positive-QTOFsplash10-05mo-9300000000-21ac15e6aeee18f1222c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Phenylenediamine 150V, Positive-QTOFsplash10-014l-9200000000-a703ee189bc526ca921d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Phenylenediamine 180V, Positive-QTOFsplash10-014i-9100000000-06e266af4900a62680ef2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Phenylenediamine 25V, Positive-QTOFsplash10-052f-9400000000-7219f4ee8ca59ed3ecc92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Phenylenediamine 35V, Positive-QTOFsplash10-0006-9000000000-1d60caf090423cc1094f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Phenylenediamine 90V, Positive-QTOFsplash10-052f-9600000000-12dcc6e2ac4da25c3ebf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Phenylenediamine 75V, Positive-QTOFsplash10-0a4l-6900000000-b333335a7099f9a8b5f32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Phenylenediamine 30V, Positive-QTOFsplash10-0a4i-0900000000-2c9680b8af4e12a2acfa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Phenylenediamine 45V, Positive-QTOFsplash10-0a4i-0900000000-e44a8b42a4a6fca2f0342021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Phenylenediamine 65V, Positive-QTOFsplash10-0006-9000000000-772244a291b18534be3c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Phenylenediamine 55V, Positive-QTOFsplash10-0006-9000000000-4fc045d75a788d609c722021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Phenylenediamine 10V, Positive-QTOFsplash10-0a4i-0900000000-c85293167c3205295bd92016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Phenylenediamine 20V, Positive-QTOFsplash10-0a4i-0900000000-a313caa7a5892d95b4152016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Phenylenediamine 40V, Positive-QTOFsplash10-0f89-9000000000-b84951cb869463c57c012016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Phenylenediamine 10V, Negative-QTOFsplash10-0a4i-0900000000-7f020be8fb005e0dfc4c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Phenylenediamine 20V, Negative-QTOFsplash10-0a4i-0900000000-7f020be8fb005e0dfc4c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Phenylenediamine 40V, Negative-QTOFsplash10-0a4i-3900000000-2d74ca8488bb9547e7802016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-25Wishart 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 IDC00014965
Chemspider ID13835179
KEGG Compound IDC19499
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkP-Phenylenediamine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID51403
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1149271
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 ]