MiMeDB: Showing metabocard for 2-Phenylacetamide (MMDBc0048336)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 21:57:25 UTC

Update Date

2024-10-17 03:35:50 UTC

Metabolite ID

MMDBc0048336

Metabolite Identification

Common Name

2-Phenylacetamide

Description

2-Phenylacetamide, also known as alpha-toluamide or benzeneacetamide, belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids. Pure crystals are plate shaped and colorless to white. 2-Phenylacetamide is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Phenylacetamide exists in all living organisms, ranging from bacteria to humans. But its (apparent) unacceptable toxic effects, the most alarming being cyanosis due to methemoglobinemia and ultimately liver and kidney damage, prompted the search for supposedly less toxic aniline derivatives such as phenacetin. Acetanilide is slightly soluble in water, and stable under most conditions. Acetanilide can be produced by reacting acetic anhydride with aniline:C6H5NH2 + (CH3CO)2O → C6H5NHCOCH3 + CH3COOHThe preparation used to be a traditional experiment in introductory organic chemistry lab classes, but it has now been widely replaced by the preparation of either paracetamol or aspirin, both of which teach the same practical techniques (especially recrystallization of the product) but which avoid the use of aniline, a suspected carcinogen. It is also a precursor in the synthesis of penicillin and other pharmaceuticals. Acetanilide is no longer used as a drug in its own right, although the success of its metabolite – paracetamol (acetaminophen) – is well known (although it is itself toxic in excessive amounts). After several conflicting results over the ensuing fifty years, it was established in 1948 that acetanilide was mostly metabolized to paracetamol (acetaminophen) in the human body, and that it was this metabolite that was responsible for the analgesic and antipyretic properties. In the 19th century acetanilide was one of a large number of compounds used as experimental photographic developers. Acetanilide is used as an inhibitor of hydrogen peroxide decomposition and is used to stabilize cellulose ester varnishes. Acetanilide is an odourless solid chemical of leaf or flake-like appearance. It has also found uses in the intermediation in rubber accelerator synthesis, dyes and dye intermediate synthesis, and camphor synthesis.

Structure

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

Synonyms

Value	Source
alpha-Phenylacetamide	Kegg
a-Phenylacetamide	Generator
Α-phenylacetamide	Generator
alpha-Toluamide	HMDB
Benzeneacetamide	HMDB
Phenyl-beta-acetylamine	HMDB
Phenylacetamide	HMDB
Phenylacetic acid amide	HMDB
a-Toluamide	HMDB
Α-toluamide	HMDB
Phenyl-b-acetylamine	HMDB
Phenyl-β-acetylamine	HMDB
Phenylacetate amide	HMDB
(alpha-)2-Phenylacetamide	HMDB
2-Phenyl-acetamide	HMDB
alpha-Toluimidic acid	HMDB
beta-Phenyl-acetylamine	HMDB

Molecular Formula

C₈H₉NO

Average Mass

135.1632

Monoisotopic Mass

135.068413915

IUPAC Name

2-phenylacetamide

Traditional Name

phenylacetamide

CAS Registry Number

103-81-1

SMILES

NC(=O)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C8H9NO/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,9,10)

InChI Key

LSBDFXRDZJMBSC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylacetamides

Direct Parent

Phenylacetamides

Alternative Parents

Substituents

Phenylacetamide
Primary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:16562 )
a small molecule (CPD-238 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.84 g/L	ALOGPS
logP	0.64	ALOGPS
logP	0.8	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	16.5	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.09 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	39.19 m³·mol⁻¹	ChemAxon
Polarizability	14.17 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-000l-6900000000-3cbbf18204f4b2de0705	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0006-9200000000-55ad84b73efd28e15062	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000l-6900000000-3cbbf18204f4b2de0705	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-9200000000-55ad84b73efd28e15062	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-9200000000-89b6db1a0325e673edcb	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-e6ef1b80ee1be92d2674	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000f-9500000000-84ba2fa898e7e6582890	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-9623a0382fbdaae6b45a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9000000000-e6bac2202565584bd5d5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0006-9000000000-0add31dc7c665b1ac05b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9200000000-e0d7e84c18f35c7ee17f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9000000000-ec10ab7c6914fd677171	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-9096a510031f5668f019	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-b99eb9c53f42664ae03a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9000000000-5c058521754d64b8aa68	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9200000000-6116ea4f3fc2b22bd23c	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0900000000-d67563d26bb591955816	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014l-4900000000-f91271d86bab54b239cd	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-7d68220f572a4f08200b	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1900000000-347d8682aa8799f5d2b4	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000x-6900000000-970db40cc13f9cc5cb64	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-0ad378c15c5c541b5749	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kf-9800000000-223258c143c5a529a9b8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9100000000-bd85826f99fe4b8cba65	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-a8f8b40d67bb9135d2b2	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9100000000-8e773ec020e370787984	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-f5a600a275c36ba02331	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-90726b17dc36e29c5299	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191949	Lactoperoxidase	Unknown	P22079	Homo sapiens
MMDBp0191951	Peroxiredoxin-6	Enzyme	P30041	Homo sapiens
MMDBp0191952	Myeloperoxidase	Unknown	P05164	Homo sapiens
MMDBp0191955	Eosinophil peroxidase	Unknown	P11678	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0010578	L-Phenylalanine	2-Phenylacetamide	eosinophil peroxidase		VMH; KEGG	30371894
MMDBr0010600	2-Phenylacetamide	Phenylacetic acid	fatty acid amide hydrolase 2		VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human feces; Human

Exposure Sources

Source Type	Activity	Data Source	Reference
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0010715

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027865

KNApSAcK ID

Not Available

Chemspider ID

7397

KEGG Compound ID

C02505

BioCyc ID

CPD-238

BiGG ID

Not Available

Wikipedia Link

Acetanilide

METLIN ID

Not Available

PubChem Compound

7680

PDB ID

Not Available

ChEBI ID

16562

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 2-Phenylacetamide (MMDBc0048336)

MOL for #<Metabolite:0x00007fdb593bed90>

3D MOL for #<Metabolite:0x00007fdb593bed90>

3D SDF for #<Metabolite:0x00007fdb593bed90>

3D-SDF for #<Metabolite:0x00007fdb593bed90>

PDB for #<Metabolite:0x00007fdb593bed90>

3D PDB for #<Metabolite:0x00007fdb593bed90>

SMILES for #<Metabolite:0x00007fdb593bed90>

INCHI for #<Metabolite:0x00007fdb593bed90>

Structure for #<Metabolite:0x00007fdb593bed90>

3D Structure for #<Metabolite:0x00007fdb593bed90>