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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:26:20 UTC

Update Date

2022-09-22 17:44:20 UTC

HMDB ID

HMDB0246417

Secondary Accession Numbers

None

Metabolite Identification

Common Name

p-Phenetidine

Description

4-ethoxyaniline, also known as 4-phenetidine or 4-aminophenetole, belongs to the class of organic compounds known as aminophenyl ethers. These are aromatic compounds that contain a phenol ether, which carries an amine group on the benzene ring. 4-ethoxyaniline is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 4-ethoxyaniline. This compound has been identified in human blood as reported by (PMID: 31557052 ). P-phenetidine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically p-Phenetidine 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Amino-4-ethoxybenzene	ChEBI
4-Aminophenetole	ChEBI
4-Aminophenyl ethyl ether	ChEBI
4-Ethoxybenzenamine	ChEBI
4-Ethoxybenzeneamine	ChEBI
4-Phenetidine	ChEBI
Ethyl p-aminophenol	ChEBI
p-Aminoethoxybenzene	ChEBI
p-Aminophenetole	ChEBI
p-Aminophenyl ethyl ether	ChEBI
p-Ethoxyaniline	ChEBI
p-Phenetidine	ChEBI
Phenetidine	ChEBI
Aminophenetole	MeSH
Ethoxyaniline	MeSH

Chemical Formula

C₈H₁₁NO

Average Molecular Weight

137.182

Monoisotopic Molecular Weight

137.084063978

IUPAC Name

4-ethoxyaniline

Traditional Name

P-ethoxyaniline

CAS Registry Number

Not Available

SMILES

CCOC1=CC=C(N)C=C1

InChI Identifier

InChI=1S/C8H11NO/c1-2-10-8-5-3-7(9)4-6-8/h3-6H,2,9H2,1H3

InChI Key

IMPPGHMHELILKG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminophenyl ethers. These are aromatic compounds that contain a phenol ether, which carries an amine group on the benzene ring.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Aminophenyl ether
Phenoxy compound
Aniline or substituted anilines
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:85505 )
substituted aniline (CHEBI:85505 )
primary amino compound (CHEBI:85505 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.64	ALOGPS
logP	1.34	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	5.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	35.25 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.97 m³·mol⁻¹	ChemAxon
Polarizability	15.43 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	133.023	30932474
DeepCCS	[M-H]-	129.212	30932474
DeepCCS	[M-2H]-	166.6	30932474
DeepCCS	[M+Na]+	141.934	30932474
AllCCS	[M+H]+	130.9	32859911
AllCCS	[M+H-H2O]+	126.4	32859911
AllCCS	[M+NH4]+	135.1	32859911
AllCCS	[M+Na]+	136.3	32859911
AllCCS	[M-H]-	129.9	32859911
AllCCS	[M+Na-2H]-	131.7	32859911
AllCCS	[M+HCOO]-	133.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
p-Phenetidine	CCOC1=CC=C(N)C=C1	2218.2	Standard polar	33892256
p-Phenetidine	CCOC1=CC=C(N)C=C1	1260.2	Standard non polar	33892256
p-Phenetidine	CCOC1=CC=C(N)C=C1	1314.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
p-Phenetidine,1TMS,isomer #1	CCOC1=CC=C(N[Si](C)(C)C)C=C1	1487.2	Semi standard non polar	33892256
p-Phenetidine,1TMS,isomer #1	CCOC1=CC=C(N[Si](C)(C)C)C=C1	1519.1	Standard non polar	33892256
p-Phenetidine,1TMS,isomer #1	CCOC1=CC=C(N[Si](C)(C)C)C=C1	1716.7	Standard polar	33892256
p-Phenetidine,2TMS,isomer #1	CCOC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	1578.5	Semi standard non polar	33892256
p-Phenetidine,2TMS,isomer #1	CCOC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	1613.9	Standard non polar	33892256
p-Phenetidine,2TMS,isomer #1	CCOC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	1693.7	Standard polar	33892256
p-Phenetidine,1TBDMS,isomer #1	CCOC1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	1725.0	Semi standard non polar	33892256
p-Phenetidine,1TBDMS,isomer #1	CCOC1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	1740.2	Standard non polar	33892256
p-Phenetidine,1TBDMS,isomer #1	CCOC1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	1878.9	Standard polar	33892256
p-Phenetidine,2TBDMS,isomer #1	CCOC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2029.6	Semi standard non polar	33892256
p-Phenetidine,2TBDMS,isomer #1	CCOC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	2024.1	Standard non polar	33892256
p-Phenetidine,2TBDMS,isomer #1	CCOC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	1936.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - p-Phenetidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-5900000000-c00b6bab3c75c777c35f	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Phenetidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Phenetidine 10V, Positive-QTOF	splash10-0079-0900000000-865f320961c0605ef718	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Phenetidine 20V, Positive-QTOF	splash10-0079-1900000000-601093e30c40a15cf2ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Phenetidine 40V, Positive-QTOF	splash10-00o0-9100000000-56059731988f0ed370bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Phenetidine 10V, Negative-QTOF	splash10-000i-0900000000-7c8b8ca064ae914492f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Phenetidine 20V, Negative-QTOF	splash10-052r-1900000000-2ef27300c09dea325e3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Phenetidine 40V, Negative-QTOF	splash10-0a4i-8900000000-ee9bbd3b66e277b98c75	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Phenetidine 10V, Positive-QTOF	splash10-000i-0900000000-6972a080f89beadeb048	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Phenetidine 20V, Positive-QTOF	splash10-03dr-6900000000-bf28b6c2721ca7a37f88	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Phenetidine 40V, Positive-QTOF	splash10-014l-9000000000-20370475e3678f01e9b9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Phenetidine 10V, Negative-QTOF	splash10-000i-1900000000-ff4ab1c5d4cdac3242ba	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Phenetidine 20V, Negative-QTOF	splash10-052f-6900000000-1452b928ef59917803dc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Phenetidine 40V, Negative-QTOF	splash10-0a4i-5900000000-1fae3e95d115a67d3ede	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21106155

KEGG Compound ID

Not Available

BioCyc ID

CPD0-2528

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

85505

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

Showing metabocard for p-Phenetidine (HMDB0246417)

MOL for HMDB0246417 (p-Phenetidine)

3D MOL for HMDB0246417 (p-Phenetidine)

3D SDF for HMDB0246417 (p-Phenetidine)

3D-SDF for HMDB0246417 (p-Phenetidine)

PDB for HMDB0246417 (p-Phenetidine)

3D PDB for HMDB0246417 (p-Phenetidine)

SMILES for HMDB0246417 (p-Phenetidine)

INCHI for HMDB0246417 (p-Phenetidine)

Structure for HMDB0246417 (p-Phenetidine)

3D Structure for HMDB0246417 (p-Phenetidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra