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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:45:39 UTC

Update Date

2022-09-22 17:44:26 UTC

HMDB ID

HMDB0255863

Secondary Accession Numbers

None

Metabolite Identification

Common Name

o-Phenetidine

Description

2-ethoxyaniline 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. Based on a literature review very few articles have been published on 2-ethoxyaniline. This compound has been identified in human blood as reported by (PMID: 31557052 ). O-phenetidine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically o-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
Ethoxyaniline	MeSH
Aminophenetole	MeSH
Phenetidine	MeSH

Chemical Formula

C₈H₁₁NO

Average Molecular Weight

137.182

Monoisotopic Molecular Weight

137.084063978

IUPAC Name

2-ethoxyaniline

Traditional Name

2-ethoxyaniline

CAS Registry Number

Not Available

SMILES

CCOC1=CC=CC=C1N

InChI Identifier

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

InChI Key

ULHFFAFDSSHFDA-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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

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	1.52	ALOGPS
logP	1.34	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Basic)	4.44	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	15.24 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]+	131.232	30932474
DeepCCS	[M-H]-	128.806	30932474
DeepCCS	[M-2H]-	165.391	30932474
DeepCCS	[M+Na]+	140.207	30932474
AllCCS	[M+H]+	129.2	32859911
AllCCS	[M+H-H2O]+	124.6	32859911
AllCCS	[M+NH4]+	133.5	32859911
AllCCS	[M+Na]+	134.8	32859911
AllCCS	[M-H]-	128.6	32859911
AllCCS	[M+Na-2H]-	130.4	32859911
AllCCS	[M+HCOO]-	132.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	12.6182 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.04 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1536.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	436.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	140.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	273.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	140.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	372.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	452.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	110.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1057.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	319.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	975.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	348.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	354.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	384.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	250.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	52.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
o-Phenetidine	CCOC1=CC=CC=C1N	1958.4	Standard polar	33892256
o-Phenetidine	CCOC1=CC=CC=C1N	1208.8	Standard non polar	33892256
o-Phenetidine	CCOC1=CC=CC=C1N	1228.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
o-Phenetidine,1TMS,isomer #1	CCOC1=CC=CC=C1N[Si](C)(C)C	1377.8	Semi standard non polar	33892256
o-Phenetidine,1TMS,isomer #1	CCOC1=CC=CC=C1N[Si](C)(C)C	1387.6	Standard non polar	33892256
o-Phenetidine,1TMS,isomer #1	CCOC1=CC=CC=C1N[Si](C)(C)C	1637.5	Standard polar	33892256
o-Phenetidine,2TMS,isomer #1	CCOC1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	1408.0	Semi standard non polar	33892256
o-Phenetidine,2TMS,isomer #1	CCOC1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	1509.3	Standard non polar	33892256
o-Phenetidine,2TMS,isomer #1	CCOC1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	1615.9	Standard polar	33892256
o-Phenetidine,1TBDMS,isomer #1	CCOC1=CC=CC=C1N[Si](C)(C)C(C)(C)C	1599.0	Semi standard non polar	33892256
o-Phenetidine,1TBDMS,isomer #1	CCOC1=CC=CC=C1N[Si](C)(C)C(C)(C)C	1605.5	Standard non polar	33892256
o-Phenetidine,1TBDMS,isomer #1	CCOC1=CC=CC=C1N[Si](C)(C)C(C)(C)C	1843.8	Standard polar	33892256
o-Phenetidine,2TBDMS,isomer #1	CCOC1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1847.0	Semi standard non polar	33892256
o-Phenetidine,2TBDMS,isomer #1	CCOC1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1916.7	Standard non polar	33892256
o-Phenetidine,2TBDMS,isomer #1	CCOC1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1896.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - o-Phenetidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-6900000000-394c4fd1681088595067	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - o-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 - o-Phenetidine 10V, Positive-QTOF	splash10-000i-0900000000-994eca19783a4f15ccf4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-Phenetidine 20V, Positive-QTOF	splash10-000i-2900000000-e5f774e5295f0377db50	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-Phenetidine 40V, Positive-QTOF	splash10-0hfx-9200000000-2978e18d54042e172252	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-Phenetidine 10V, Negative-QTOF	splash10-000i-0900000000-e9589fb1948343f5e623	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-Phenetidine 20V, Negative-QTOF	splash10-052r-2900000000-009025cf2d3e3bb3107a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-Phenetidine 40V, Negative-QTOF	splash10-0a4l-9400000000-a86ac334942897134587	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	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

21106580

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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 o-Phenetidine (HMDB0255863)

MOL for HMDB0255863 (o-Phenetidine)

3D MOL for HMDB0255863 (o-Phenetidine)

3D SDF for HMDB0255863 (o-Phenetidine)

3D-SDF for HMDB0255863 (o-Phenetidine)

PDB for HMDB0255863 (o-Phenetidine)

3D PDB for HMDB0255863 (o-Phenetidine)

SMILES for HMDB0255863 (o-Phenetidine)

INCHI for HMDB0255863 (o-Phenetidine)

Structure for HMDB0255863 (o-Phenetidine)

3D Structure for HMDB0255863 (o-Phenetidine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra