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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:52:21 UTC
Update Date2022-03-07 02:53:29 UTC
HMDB IDHMDB0032865
Secondary Accession Numbers
  • HMDB32865
Metabolite Identification
Common NameN-Phenyl-2-naphthylamine
DescriptionN-Phenyl-2-naphthylamine, also known as neozone or 2-phenylaminonaphthalene, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. N-Phenyl-2-naphthylamine has been detected, but not quantified in, root vegetables. This could make N-phenyl-2-naphthylamine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on N-Phenyl-2-naphthylamine.
Structure
Data?1563862319
Synonyms
ValueSource
NeozoneKegg
2-PhenylaminonaphthaleneKegg
2-(N-phenylamino)NaphthaleneHMDB
2-AnilinonaphthaleneHMDB, MeSH
2-NaphthylphenylamineHMDB
Ac eto PBNHMDB
aceto PBNHMDB
AgeriteHMDB
Agerite powderHMDB
AK 1 (stabilizer)HMDB
AnilinonaphthaleneHMDB
Antioxidant 116HMDB
Antioxidant DHMDB
Antioxidant PBNHMDB
Antioxygene MCHMDB
beta -NaphthylphenylamineHMDB
beta-NaphthylphenylamineHMDB
Fenyl-beta -naftylaminHMDB
Fenyl-beta-naftylaminHMDB
N-(2-Naphthyl)-N-phenylamineHMDB
N-(2-Naphthyl)anilineHMDB
N-2-NaphthylanilineHMDB
N-beta -Naphthyl-N-phenylamineHMDB
N-beta-Naphthyl-N-phenylamineHMDB
N-Fenyl-2-aminonaftalenHMDB
N-Phenyl-2-naphthalenamineHMDB
N-Phenyl-beta -naphthylamineHMDB
N-Phenyl-beta-naphthylamineHMDB
N-Phenylnaphthalen-2-amineHMDB
Naftam 2HMDB
Neosone DHMDB, MeSH
Neozon DHMDB, MeSH
Neozone DHMDB
Nilox pbnaHMDB
Noclizer DHMDB
Nocrac DHMDB
Nonox DHMDB
Nonox DNHMDB
Nonox dnstabilizer arHMDB
P.b.NHMDB
PBNHMDB
PBNAHMDB
Phenyl-2-naphthylamineHMDB
Phenyl-beta -naphthylamineHMDB
Phenyl-beta-naphthylamineHMDB
Phenyl-beta-naphtilamineHMDB
Stabilator a.rHMDB
Stabilizator arHMDB
Stabilizer arHMDB
Vulkanox PBNHMDB
Phenyl beta-naphthylamineMeSH, HMDB
Chemical FormulaC16H13N
Average Molecular Weight219.2811
Monoisotopic Molecular Weight219.104799421
IUPAC NameN-phenylnaphthalen-2-amine
Traditional Nameanilinonaphthalene
CAS Registry Number135-88-6
SMILES
N(C1=CC=CC=C1)C1=CC2=CC=CC=C2C=C1
InChI Identifier
InChI=1S/C16H13N/c1-2-8-15(9-3-1)17-16-11-10-13-6-4-5-7-14(13)12-16/h1-12,17H
InChI KeyKEQFTVQCIQJIQW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Aniline or substituted anilines
  • Monocyclic benzene moiety
  • Secondary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point108 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.31 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.38Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0026 g/LALOGPS
logP4.53ALOGPS
logP4.4ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)0.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity70.99 m³·mol⁻¹ChemAxon
Polarizability25.21 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+150.47531661259
DarkChem[M-H]-151.82231661259
DeepCCS[M+H]+152.19730932474
DeepCCS[M-H]-149.80130932474
DeepCCS[M-2H]-183.03430932474
DeepCCS[M+Na]+158.15530932474
AllCCS[M+H]+150.332859911
AllCCS[M+H-H2O]+146.232859911
AllCCS[M+NH4]+154.232859911
AllCCS[M+Na]+155.332859911
AllCCS[M-H]-154.932859911
AllCCS[M+Na-2H]-154.032859911
AllCCS[M+HCOO]-153.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Phenyl-2-naphthylamineN(C1=CC=CC=C1)C1=CC2=CC=CC=C2C=C13191.9Standard polar33892256
N-Phenyl-2-naphthylamineN(C1=CC=CC=C1)C1=CC2=CC=CC=C2C=C12159.0Standard non polar33892256
N-Phenyl-2-naphthylamineN(C1=CC=CC=C1)C1=CC2=CC=CC=C2C=C12234.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Phenyl-2-naphthylamine,1TMS,isomer #1C[Si](C)(C)N(C1=CC=CC=C1)C1=CC=C2C=CC=CC2=C12099.0Semi standard non polar33892256
N-Phenyl-2-naphthylamine,1TMS,isomer #1C[Si](C)(C)N(C1=CC=CC=C1)C1=CC=C2C=CC=CC2=C12203.3Standard non polar33892256
N-Phenyl-2-naphthylamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1)C1=CC=C2C=CC=CC2=C12311.1Semi standard non polar33892256
N-Phenyl-2-naphthylamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1)C1=CC=C2C=CC=CC2=C12402.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Phenyl-2-naphthylamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gbc-2960000000-e541d4d4aba1b6b4ecdf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Phenyl-2-naphthylamine 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 - N-Phenyl-2-naphthylamine LC-ESI-qTof , Positive-QTOFsplash10-014r-0980000000-3e9c69c3e19f4df1aa5e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Phenyl-2-naphthylamine , positive-QTOFsplash10-0006-0920000000-335617431b110558af162017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Phenyl-2-naphthylamine LC-ESI-QFT , positive-QTOFsplash10-00di-0390000000-92378018db10ff7f51f32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Phenyl-2-naphthylamine ESI-ITFT , positive-QTOFsplash10-00di-0390000000-9109067645222d6540902017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Phenyl-2-naphthylamine APCI-ITFT , positive-QTOFsplash10-00dl-0490000000-93130be26fed1df7b7f52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 45V, Positive-QTOFsplash10-006x-3790000000-f72bf447a80c1a144cba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 60V, Positive-QTOFsplash10-0006-4920000000-ba2665fa7d2a60fea21d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 35V, Positive-QTOFsplash10-00di-0390000000-95156cc3b2db218e93612021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 30V, Positive-QTOFsplash10-00di-0090000000-bb86100e04b4ca84d8dc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 15V, Positive-QTOFsplash10-00di-0090000000-10950191b652455406922021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 35V, Positive-QTOFsplash10-00di-0390000000-5e0507a1b4c1fe30002a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 75V, Positive-QTOFsplash10-0006-3900000000-47a3dbcdab95fc879fe72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 90V, Positive-QTOFsplash10-00kf-3900000000-6a971670a608e371e0892021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 10V, Positive-QTOFsplash10-00di-0090000000-54be44e455c90d93e5222016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 20V, Positive-QTOFsplash10-00di-0190000000-2ab649fc5c68a4fb38a12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 40V, Positive-QTOFsplash10-0gbc-6920000000-57dd3b6e723efa162c722016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 10V, Negative-QTOFsplash10-014i-0090000000-9027f8ee8c611f42cf452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 20V, Negative-QTOFsplash10-014i-0090000000-2269f7c73b9fdd2b861c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 40V, Negative-QTOFsplash10-016u-4930000000-8083e8e81d16aaa58cef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 10V, Negative-QTOFsplash10-014i-0090000000-2019304f8cc1a03c307e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 20V, Negative-QTOFsplash10-014i-0090000000-2019304f8cc1a03c307e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 40V, Negative-QTOFsplash10-014i-0390000000-d9ff17cf453752c5f0302021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 10V, Positive-QTOFsplash10-00di-0090000000-48637c4bed0a487a06c12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 20V, Positive-QTOFsplash10-00di-0090000000-48637c4bed0a487a06c12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Phenyl-2-naphthylamine 40V, Positive-QTOFsplash10-014l-0950000000-e8d760bb64add21dae262021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010843
KNApSAcK IDC00039881
Chemspider ID8355
KEGG Compound IDC14694
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8679
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1267641
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .