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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 15:45:43 UTC
Update Date2021-09-26 23:11:02 UTC
HMDB IDHMDB0255864
Secondary Accession NumbersNone
Metabolite Identification
Common Nameo-Phenylenediamine
Description1,2-phenylenediamine, also known as 1,2-diaminobenzene or 2-aminoaniline, 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 1,2-phenylenediamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). O-phenylenediamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically o-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
1,2-DiaminobenzeneChEBI
2-AminoanilineChEBI
2-Phenylene diamineChEBI
O-PhenylenediamineChEBI
OPDAChEBI
Phenylene-1,2-dimaineChEBI
1,2-Diaminobenzene dihydrochlorideMeSH
2,3-DiaminobenzeneMeSH
Ortho-phenylenediamineMeSH
OrthophenylenediamineMeSH
1,2-PhenylenediamineMeSH
Chemical FormulaC6H8N2
Average Molecular Weight108.144
Monoisotopic Molecular Weight108.068748266
IUPAC Namebenzene-1,2-diamine
Traditional Nameo-phenylenediamine
CAS Registry NumberNot Available
SMILES
NC1=CC=CC=C1N
InChI Identifier
InChI=1S/C6H8N2/c7-5-3-1-2-4-6(5)8/h1-4H,7-8H2
InChI KeyGEYOCULIXLDCMW-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-0.08ALOGPS
logP0.32ChemAxon
logS-0.14ALOGPS
pKa (Strongest Basic)4.74ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.04 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.46 m³·mol⁻¹ChemAxon
Polarizability11.61 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]+124.73730932474
DeepCCS[M-H]-122.70330932474
DeepCCS[M-2H]-158.42330932474
DeepCCS[M+Na]+133.10330932474
AllCCS[M+H]+124.132859911
AllCCS[M+H-H2O]+119.232859911
AllCCS[M+NH4]+128.732859911
AllCCS[M+Na]+130.132859911
AllCCS[M-H]-120.132859911
AllCCS[M+Na-2H]-122.732859911
AllCCS[M+HCOO]-125.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
o-PhenylenediamineNC1=CC=CC=C1N2160.8Standard polar33892256
o-PhenylenediamineNC1=CC=CC=C1N1147.4Standard non polar33892256
o-PhenylenediamineNC1=CC=CC=C1N1231.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
o-Phenylenediamine,1TMS,isomer #1C[Si](C)(C)NC1=CC=CC=C1N1420.2Semi standard non polar33892256
o-Phenylenediamine,1TMS,isomer #1C[Si](C)(C)NC1=CC=CC=C1N1366.1Standard non polar33892256
o-Phenylenediamine,1TMS,isomer #1C[Si](C)(C)NC1=CC=CC=C1N2072.3Standard polar33892256
o-Phenylenediamine,2TMS,isomer #1C[Si](C)(C)NC1=CC=CC=C1N[Si](C)(C)C1519.2Semi standard non polar33892256
o-Phenylenediamine,2TMS,isomer #1C[Si](C)(C)NC1=CC=CC=C1N[Si](C)(C)C1523.9Standard non polar33892256
o-Phenylenediamine,2TMS,isomer #1C[Si](C)(C)NC1=CC=CC=C1N[Si](C)(C)C1722.2Standard polar33892256
o-Phenylenediamine,2TMS,isomer #2C[Si](C)(C)N(C1=CC=CC=C1N)[Si](C)(C)C1456.8Semi standard non polar33892256
o-Phenylenediamine,2TMS,isomer #2C[Si](C)(C)N(C1=CC=CC=C1N)[Si](C)(C)C1522.5Standard non polar33892256
o-Phenylenediamine,2TMS,isomer #2C[Si](C)(C)N(C1=CC=CC=C1N)[Si](C)(C)C1832.4Standard polar33892256
o-Phenylenediamine,3TMS,isomer #1C[Si](C)(C)NC1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C1603.4Semi standard non polar33892256
o-Phenylenediamine,3TMS,isomer #1C[Si](C)(C)NC1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C1618.4Standard non polar33892256
o-Phenylenediamine,3TMS,isomer #1C[Si](C)(C)NC1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C1660.3Standard polar33892256
o-Phenylenediamine,4TMS,isomer #1C[Si](C)(C)N(C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1607.3Semi standard non polar33892256
o-Phenylenediamine,4TMS,isomer #1C[Si](C)(C)N(C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1768.2Standard non polar33892256
o-Phenylenediamine,4TMS,isomer #1C[Si](C)(C)N(C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1583.3Standard polar33892256
o-Phenylenediamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC=C1N1644.9Semi standard non polar33892256
o-Phenylenediamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC=C1N1567.4Standard non polar33892256
o-Phenylenediamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC=C1N2238.3Standard polar33892256
o-Phenylenediamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC=C1N[Si](C)(C)C(C)(C)C1992.7Semi standard non polar33892256
o-Phenylenediamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC=C1N[Si](C)(C)C(C)(C)C1933.5Standard non polar33892256
o-Phenylenediamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC=C1N[Si](C)(C)C(C)(C)C2005.4Standard polar33892256
o-Phenylenediamine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1N)[Si](C)(C)C(C)(C)C1897.1Semi standard non polar33892256
o-Phenylenediamine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1N)[Si](C)(C)C(C)(C)C1928.5Standard non polar33892256
o-Phenylenediamine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1N)[Si](C)(C)C(C)(C)C2022.3Standard polar33892256
o-Phenylenediamine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2207.8Semi standard non polar33892256
o-Phenylenediamine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2226.7Standard non polar33892256
o-Phenylenediamine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2056.3Standard polar33892256
o-Phenylenediamine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2406.2Semi standard non polar33892256
o-Phenylenediamine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2486.5Standard non polar33892256
o-Phenylenediamine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2063.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - o-Phenylenediamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-7900000000-cd9fc3f165b4c29de6592021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - o-Phenylenediamine 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 - o-Phenylenediamine 10V, Positive-QTOFsplash10-0a4l-8900000000-10aa89c29fc401792bad2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - o-Phenylenediamine 20V, Positive-QTOFsplash10-052f-9400000000-1f63aa0331c1e230b5e72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - o-Phenylenediamine 40V, Positive-QTOFsplash10-0gbc-9000000000-2da1c7a9eb86c364a85c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - o-Phenylenediamine 10V, Negative-QTOFsplash10-0a4i-0900000000-21af471a60cea645b0882016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - o-Phenylenediamine 20V, Negative-QTOFsplash10-0a4i-2900000000-5983082d69867c7ce6122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - o-Phenylenediamine 40V, Negative-QTOFsplash10-0a4i-9800000000-da59977d081e40f9baf92016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H 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 NMR1H NMR Spectrum (1D, 400 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 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 NMR13C NMR Spectrum (1D, 700 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 NMR1H NMR Spectrum (1D, 800 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, 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 IDNot Available
Chemspider ID13837582
KEGG Compound IDC14402
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkO-Phenylenediamine
METLIN IDNot Available
PubChem Compound7243
PDB IDNot Available
ChEBI ID34043
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 ]