N-Phenylacetylglycine (YMDB01568)

Identification

YMDB ID

YMDB01568

Name

N-Phenylacetylglycine

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Phenylacetylglycine, also known as phenaceturic acid or phenacetate, belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Phenylacetylglycine is an extremely weak basic (essentially neutral) compound (based on its pKa). Phenylacetylglycine exists in all eukaryotes, ranging from yeast to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

((Phenylacetyl)amino)acetic acid
[(Phenylacetyl)amino]acetate
[(Phenylacetyl)amino]acetic acid
N-(Phenylacetyl)-glycine
N-(Phenylacetyl)glycine
N-Phenacetylglycine
N-Phenylacetylglycine
PAA
PAG
Phenacetate
Phenacetic acid
Phenaceturate
Phenaceturic acid
Phenacetylglycine
Phenylacetyl glycine
Phenylacetylglycine

CAS number

500-98-1

Weight

Average: 193.1992
Monoisotopic: 193.073893223

InChI Key

UTYVDVLMYQPLQB-UHFFFAOYSA-N

InChI

InChI=1S/C10H11NO3/c12-9(11-7-10(13)14)6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)(H,13,14)

IUPAC Name

2-(2-phenylacetamido)acetic acid

Traditional IUPAC Name

phenylacetylglycine

Chemical Formula

C₁₀H₁₁NO₃

SMILES

OC(=O)CNC(=O)CC1=CC=CC=C1

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Monocyclic benzene moiety
Benzenoid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:27480 )
monocarboxylic acid amide (CHEBI:27480 )
N-acylglycine (CHEBI:27480 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	7.3 mg/mL at 11 oC [BEILSTEIN]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.66 g/L	ALOGPS
logP	0.51	ALOGPS
logP	0.51	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.99	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	50.17 m³·mol⁻¹	ChemAxon
Polarizability	19.09 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
1000 ± 50 µM	YEB media with 0.5 mM glucose	aerobic	Brewer's yeast	Experimentally Determined Not Available
Conversion Details Here

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-96f6d1819364e0910beb	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udl-5930000000-6e0622de46a05b80d685	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-9610000000-b8948d031afc0e4b8f78	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-96f6d1819364e0910beb	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udl-5930000000-6e0622de46a05b80d685	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-9610000000-b8948d031afc0e4b8f78	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9500000000-50b56f103c1a79f65878	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9200000000-5d39e42ac2b4d7b6f726	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004l-9100000000-134ddfbf19f2ee4e9260	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-9656d3b4670efd4db2e3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-9cf5ff47848cf5bf99b2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	splash10-0006-9000000000-f37d59edacbcf679b420	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9200000000-92c7f1e2376eb0e84b36	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-002f-9200000000-c48677787f705755d93f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0006-9300000000-dd5f78904d0d0dacb641	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9300000000-1acb6b8d75e7381ccbde	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0596-9100000000-415a6a1ccc4a5a25ad4f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-002f-9100000000-52063d451d15512ae652	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0006-9000000000-b4cfc8b9dad7406c720f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-002f-9000000000-88eadbe8bb1b30f341b0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-abf76489fbf1b18e56aa	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-00di-9000000000-1168dca79ce76e8ff744	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-709de7804cd48ddac3b5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00di-9000000000-668624127e5eb3cd947a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-f0284ab582fc7a2b28c4	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-9600000000-96499e21a08e5d190040	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00fr-9200000000-aeac60944271030f9751	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00bc-9000000000-4caba04f2e229a8013b4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-899f25422883181dbe57	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-4900000000-433c13250fe2463708f4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9200000000-0b6ae74cd7a7ddce62d7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-e21745e55a3af36629b3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-078d0d5a533b72168681	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	27480
HMDB ID	HMDB00821
Pubchem Compound ID	68144
Kegg ID	C05596
ChemSpider ID	61452
FOODB ID	FDB022266
Wikipedia ID	Not Available
BioCyc ID	CPD-11715

Structure for #<Compound:0xb67156f4>