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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:52 UTC

Update Date

2023-02-21 17:22:33 UTC

HMDB ID

HMDB0032630

Secondary Accession Numbers

HMDB32630

Metabolite Identification

Common Name

2'-Aminoacetophenone

Description

2'-Aminoacetophenone, also known as O-acetylaniline or 1-acetyl-2-aminobenzene, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 2'-Aminoacetophenone exists as a solid, slightly soluble (in water), and an extremely weak acidic (essentially neutral) compound (based on its pKa). Within the cell, 2'-aminoacetophenone is primarily located in the cytoplasm. 2'-Aminoacetophenone is a sweet, foxy, and grape tasting compound that can be found in fruits and milk and milk products. This makes 2'-aminoacetophenone a potential biomarker for the consumption of these food products.

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-Acetyl-2-aminobenzene	ChEBI
2-Acetylaniline	ChEBI
2-Acetylphenylamine	ChEBI
2-Aminoacetophenone	ChEBI
5 Kaal	ChEBI
O-Acetylaniline	ChEBI
O-Aminoacetylbenzene	ChEBI
O-Aminophenyl methyl ketone	ChEBI
Ortho-aminoacetophenone	ChEBI
1-(2-Aminophenyl)-ethanone	HMDB
1-(2-Aminophenyl)ethanone, 9ci	HMDB
1-(Aminophenyl)-ethanone	HMDB
2'-Amonioacetophenone	HMDB
FEMA 3906	HMDB
2-Aminoacetophenone hydrochloride	HMDB
O-Aminoacetophenone	HMDB
2'-Aminoacetophenone	ChEBI

Chemical Formula

C₈H₉NO

Average Molecular Weight

135.1632

Monoisotopic Molecular Weight

135.068413915

IUPAC Name

1-(2-aminophenyl)ethan-1-one

Traditional Name

O-aminoacetophenone

CAS Registry Number

551-93-9

SMILES

CC(=O)C1=CC=CC=C1N

InChI Identifier

InChI=1S/C8H9NO/c1-6(10)7-4-2-3-5-8(7)9/h2-5H,9H2,1H3

InChI Key

GTDQGKWDWVUKTI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Acetophenone
Benzoyl
Aryl alkyl ketone
Aniline or substituted anilines
Benzenoid
Monocyclic benzene moiety
Vinylogous amide
Amine
Primary amine
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032630)
Cytoplasm (HMDB: HMDB0032630)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032630)

Source

Endogenous

Endogenous (HMDB: HMDB0032630)

Plant

Plant (HMDB: HMDB0032630)

Animal

Animal (HMDB: HMDB0032630)

Exogenous

Food

Food (HMDB: HMDB0032630)

Fruit

Fruits (FooDB: FOOD00871)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	20 °C	Not Available
Boiling Point	85.00 to 90.00 °C. @ 0.50 mm Hg	The Good Scents Company Information System
Water Solubility	3555 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.63	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.7 g/L	ALOGPS
logP	0.98	ALOGPS
logP	1.35	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	16.26	ChemAxon
pKa (Strongest Basic)	2.56	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.09 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	41.16 m³·mol⁻¹	ChemAxon
Polarizability	14.38 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	129.077	31661259
DarkChem	[M-H]-	123.65	31661259
DeepCCS	[M+H]+	129.831	30932474
DeepCCS	[M-H]-	127.292	30932474
DeepCCS	[M-2H]-	163.337	30932474
DeepCCS	[M+Na]+	138.188	30932474
AllCCS	[M+H]+	127.8	32859911
AllCCS	[M+H-H2O]+	123.1	32859911
AllCCS	[M+NH4]+	132.2	32859911
AllCCS	[M+Na]+	133.5	32859911
AllCCS	[M-H]-	126.5	32859911
AllCCS	[M+Na-2H]-	128.2	32859911
AllCCS	[M+HCOO]-	130.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2'-Aminoacetophenone	CC(=O)C1=CC=CC=C1N	2261.7	Standard polar	33892256
2'-Aminoacetophenone	CC(=O)C1=CC=CC=C1N	1279.1	Standard non polar	33892256
2'-Aminoacetophenone	CC(=O)C1=CC=CC=C1N	1331.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2'-Aminoacetophenone,1TMS,isomer #1	CC(=O)C1=CC=CC=C1N[Si](C)(C)C	1450.3	Semi standard non polar	33892256
2'-Aminoacetophenone,1TMS,isomer #1	CC(=O)C1=CC=CC=C1N[Si](C)(C)C	1515.9	Standard non polar	33892256
2'-Aminoacetophenone,2TMS,isomer #1	CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	1507.5	Semi standard non polar	33892256
2'-Aminoacetophenone,2TMS,isomer #1	CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	1662.3	Standard non polar	33892256
2'-Aminoacetophenone,1TBDMS,isomer #1	CC(=O)C1=CC=CC=C1N[Si](C)(C)C(C)(C)C	1695.9	Semi standard non polar	33892256
2'-Aminoacetophenone,1TBDMS,isomer #1	CC(=O)C1=CC=CC=C1N[Si](C)(C)C(C)(C)C	1741.0	Standard non polar	33892256
2'-Aminoacetophenone,2TBDMS,isomer #1	CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1940.9	Semi standard non polar	33892256
2'-Aminoacetophenone,2TBDMS,isomer #1	CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2045.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2'-Aminoacetophenone EI-B (Non-derivatized)	splash10-00y3-8900000000-5b770b73f4fd1d3c31b6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2'-Aminoacetophenone EI-B (Non-derivatized)	splash10-00y3-8900000000-5b770b73f4fd1d3c31b6	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'-Aminoacetophenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00y3-9800000000-87de04cb36dec199538d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'-Aminoacetophenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'-Aminoacetophenone 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 - 2'-Aminoacetophenone 10V, Positive-QTOF	splash10-000i-0900000000-390dd0a9927907e2e665	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 20V, Positive-QTOF	splash10-000i-2900000000-ba632cb2c303bfdf5ad1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 40V, Positive-QTOF	splash10-0gbc-9300000000-05733141b0e2d5c6345b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 10V, Negative-QTOF	splash10-001i-0900000000-97c834df79371be37b1a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 20V, Negative-QTOF	splash10-001l-6900000000-f8a3d865b06a13af1cd8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 40V, Negative-QTOF	splash10-0006-9300000000-cac192025ffacc504db8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 10V, Negative-QTOF	splash10-001i-2900000000-e2fa340834ceeb952438	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 20V, Negative-QTOF	splash10-0006-9400000000-72b13192818d59042978	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 40V, Negative-QTOF	splash10-00kf-9300000000-ec964628a8bc2468c319	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 10V, Positive-QTOF	splash10-00kr-0900000000-bf06926af58b9dc8bf28	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 20V, Positive-QTOF	splash10-00kf-9800000000-294904f564e143ece6b4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 40V, Positive-QTOF	splash10-0fr6-9100000000-9986bebd23c977343917	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

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

FDB010574

KNApSAcK ID

Not Available

Chemspider ID

13859235

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11086

PDB ID

VNJ

ChEBI ID

91110

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1062161

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2'-Aminoacetophenone (HMDB0032630)

MOL for HMDB0032630 (2'-Aminoacetophenone)

3D MOL for HMDB0032630 (2'-Aminoacetophenone)

3D SDF for HMDB0032630 (2'-Aminoacetophenone)

3D-SDF for HMDB0032630 (2'-Aminoacetophenone)

PDB for HMDB0032630 (2'-Aminoacetophenone)

3D PDB for HMDB0032630 (2'-Aminoacetophenone)

SMILES for HMDB0032630 (2'-Aminoacetophenone)

INCHI for HMDB0032630 (2'-Aminoacetophenone)

Structure for HMDB0032630 (2'-Aminoacetophenone)

3D Structure for HMDB0032630 (2'-Aminoacetophenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra