An official website of the United States government

L-alpha-Phenylglycine

PubChem CID
6931074
Structure
L-alpha-Phenylglycine_small.png
L-alpha-Phenylglycine_3D_Structure.png
L-alpha-Phenylglycine__Crystal_Structure.png
Molecular Formula
Synonyms
  • L-alpha-Phenylglycine
  • DL-aminophenyl acetic acid
  • L-alpha-phenylglycine zwitterion
  • CHEBI:136765
  • DL-2-amino-2-phenyl ethanoic acid
Molecular Weight
151.16 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2006-07-28
  • Modify:
    2025-01-25
Description
L-alpha-phenylglycine zwitterion is an L-alpha-amino acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of L-alpha-phenylglycine; major species at pH 7.3. It is a tautomer of a L-alpha-phenylglycine.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
L-alpha-Phenylglycine.png

1.2 3D Conformer

1.3 Crystal Structures

COD Number
Associated Article
Dalhus, Bjørn; Görbitz, Carl Henrik. DL-Aminophenylacetic acid. Acta Crystallographica Section C 1999;55(6):IUC9900061-. DOI: 10.1107/S0108270199099291
Crystal Structure Depiction
Crystal Structure Depiction
Hermann-Mauguin space group symbol
P 1 21/c 1
Hall space group symbol
-P 2ybc
Space group number
14
a
15.7794 Å
b
4.8525 Å
c
9.8771 Å
α
90.00 °
β
97.9520 °
γ
90.00 °
Z
4
Z'
1
Residual factor
0.097
Weighted residual factor
0.158

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
H-Phg-OH
Sequence
X
HELM
PEPTIDE1{[Phg]}$$$$
IUPAC
2-phenyl-L-glycine

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(2S)-2-azaniumyl-2-phenylacetate
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

3.1.2 InChI

InChI=1S/C8H9NO2/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7H,9H2,(H,10,11)/t7-/m0/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.3 InChIKey

ZGUNAGUHMKGQNY-ZETCQYMHSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.4 SMILES

C1=CC=C(C=C1)[C@@H](C(=O)[O-])[NH3+]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C8H9NO2
Computed by PubChem 2.1 (PubChem release 2019.06.18)

3.3 Other Identifiers

3.3.1 CAS

3.3.2 ChEBI ID

3.3.3 Metabolomics Workbench ID

3.3.4 Wikidata

3.4 Synonyms

3.4.1 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
151.16 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3
Property Value
-1.1
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
151.063328530 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
151.063328530 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
67.8 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
11
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
136
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2019.01.04)

5 Spectral Information

5.1 1D NMR Spectra

5.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian CFT-20
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
237647
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

5.1.2 13C NMR Spectra

1 of 2
Source of Sample
Fluka AG, Buchs, Switzerland
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
237647
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

5.2 IR Spectra

5.2.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
Fluka Chemie AG, Buchs, Switzerland
Catalog Number
78565
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
KBr1
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Spectrochem Pvt. Ltd.
Catalog Number
116204
Copyright
Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

5.2.2 ATR-IR Spectra

1 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Spectrochem Pvt. Ltd.
Catalog Number
116204
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Sample
Aldrich
Catalog Number
237647
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

5.3 Raman Spectra

1 of 2
Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories
Source of Sample
Spectrochem Pvt. Ltd., India
Catalog Number
116204
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Catalog Number
237647
Copyright
Copyright © 2017-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

7 Chemical Vendors

8 Pharmacology and Biochemistry

8.1 Biochemical Reactions

9 Literature

9.1 Consolidated References

9.2 Chemical Co-Occurrences in Literature

9.3 Chemical-Gene Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 Chemical Co-Occurrences in Patents

10.3 Chemical-Disease Co-Occurrences in Patents

10.4 Chemical-Gene Co-Occurrences in Patents

11 Classification

11.1 ChEBI Ontology

12 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChEBI
  3. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  4. Metabolomics Workbench
  5. Rhea - Annotated Reactions Database
    LICENSE
    Rhea has chosen to apply the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/). This means that you are free to copy, distribute, display and make commercial use of the database in all legislations, provided you credit (cite) Rhea.
    https://www.rhea-db.org/help/license-disclaimer
  6. SpectraBase
  7. Wikidata
  8. PubChem
CONTENTS