Milk Composition Database: Showing metabocard for 2-Phenylglycine (BMDB0002210)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:52:42 UTC

Update Date

2020-04-22 15:10:13 UTC

MCDB ID

BMDB0002210

Secondary Accession Numbers

BMDB02210

Metabolite Identification

Common Name

2-Phenylglycine

Description

2-Phenylglycine, also known as a-amino-a-toluate or L-PHG amino acid, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). 2-Phenylglycine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-2-phenylacetic acid	ChEBI
alpha-Amino-alpha-toluic acid	ChEBI
alpha-Aminobenzeneacetic acid	ChEBI
alpha-Aminophenylacetic acid	ChEBI
Amino(phenyl)acetic acid	ChEBI
Amino-phenyl-acetic acid	ChEBI
DL-2-Phenylglycine	ChEBI
DL-alpha-Phenylglycine	ChEBI
DL-Phenylglycine	ChEBI
2-Amino-2-phenylacetate	Generator
a-Amino-a-toluate	Generator
a-Amino-a-toluic acid	Generator
alpha-Amino-alpha-toluate	Generator
Α-amino-α-toluate	Generator
Α-amino-α-toluic acid	Generator
a-Aminobenzeneacetate	Generator
a-Aminobenzeneacetic acid	Generator
alpha-Aminobenzeneacetate	Generator
Α-aminobenzeneacetate	Generator
Α-aminobenzeneacetic acid	Generator
a-Aminophenylacetate	Generator
a-Aminophenylacetic acid	Generator
alpha-Aminophenylacetate	Generator
Α-aminophenylacetate	Generator
Α-aminophenylacetic acid	Generator
Amino(phenyl)acetate	Generator
Amino-phenyl-acetate	Generator
DL-a-Phenylglycine	Generator
DL-Α-phenylglycine	Generator
2-Phenylglycine, (D)-isomer	HMDB
2-Phenylglycine, (DL)-isomer	HMDB
2-Phenylglycine, (L)-isomer	HMDB
D-Phenylglycine	HMDB
L-PHG Amino acid	HMDB
L-Phenylglycine	HMDB
(+/-)-a-phenylglycine	HMDB
(+/-)-alpha-phenylglycine	HMDB
2-Phenyl-glycine	HMDB
alpha-Amino-benzeneacetate	HMDB
alpha-Amino-benzeneacetic acid	HMDB
alpha-Phenylgycine	HMDB
Aminophenylacetic acid	HMDB
DL-2-Phenyl-glycine	HMDB
DL-a-Aminophenylacetate	HMDB
DL-a-Aminophenylacetic acid	HMDB
DL-alpha-Aminophenylacetate	HMDB
DL-alpha-Aminophenylacetic acid	HMDB
DL-alpha-Phenylaminoacetate	HMDB
DL-alpha-Phenylaminoacetic acid	HMDB
a-Phenylglycine	HMDB
Α-phenylglycine	HMDB
2-Phenylglycine	ChEBI

Chemical Formula

C₈H₉NO₂

Average Molecular Weight

151.1626

Monoisotopic Molecular Weight

151.063328537

IUPAC Name

2-amino-2-phenylacetic acid

Traditional Name

(+/-)-α-phenylglycine

CAS Registry Number

2835-06-5

SMILES

NC(C(O)=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C8H9NO2/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7H,9H2,(H,10,11)

InChI Key

ZGUNAGUHMKGQNY-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:55484 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	290 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	115 mg/mL at 100 °C	Not Available
LogP	-2.07	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	-1.5	ALOGPS
logP	-1.5	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	2.23	ChemAxon
pKa (Strongest Basic)	8.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	40.36 m³·mol⁻¹	ChemAxon
Polarizability	15.18 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	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 (1 TMS)	splash10-0a4i-4900000000-4255b20d77dfc7511860	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-004i-1900000000-3571e0e48ff4beba6a5e	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-0900000000-75eb2bf8dd6d3575536f	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4i-4900000000-4255b20d77dfc7511860	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004i-1900000000-3571e0e48ff4beba6a5e	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9800000000-58c48ae51acc717c1930	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00b9-7900000000-460333cd7895c5407da6	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-0900000000-ea6e7d2a2146ec7f47b9	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9000000000-1ae3b98cb7952290571c	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9000000000-745a972e5abcea06d0ac	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0900000000-977fbf01f8ff42a9231c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0900000000-c3f64210f913886692d3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0900000000-04069023db5873b4f33e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-000i-0900000000-414e87d5deb5c1f31fbc	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-25b921efdc005d4819f7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-b2560a30a952ffe14e38	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-2b98b92efb70b302e8fb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0a4i-0900000000-db6b6c60d615199bc91a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-000i-0900000000-05ebbfa66074b9020bbb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004i-9100000000-27515443765f9a2fdbb3	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-000i-0900000000-ae424cdba1a927209aeb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0570-5900000000-0a72ab0aea3a129b60e2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-585408622b96e7bba4ca	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-052r-2900000000-b367ccf79396e1db6315	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004i-9000000000-aac2a13eeb7dfaf7356f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9300000000-fd4a6d143eb6f2f03d79	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pb9-0900000000-47dcc609b317b1089dd9	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-080013be9eb2adefb917	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9600000000-676402cb8f38f4574e49	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-37d07671d220649ab939	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2900000000-f5b2973e83cd73f4c3fb	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-02f46a98c0b5bed99b97	2017-09-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 28306241	details

External Links

HMDB ID

HMDB0002210

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022909

KNApSAcK ID

Not Available

Chemspider ID

3732

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenylglycine

METLIN ID

6549

PubChem Compound

3866

PDB ID

Not Available

ChEBI ID

55484

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]

Showing metabocard for 2-Phenylglycine (BMDB0002210)

Structure for BMDB0002210 (2-Phenylglycine)