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4-Hydroxyphenylglycine

PubChem CID
92143
Structure
4-Hydroxyphenylglycine_small.png
4-Hydroxyphenylglycine_3D_Structure.png
Molecular Formula
Synonyms
  • 2-amino-2-(4-hydroxyphenyl)acetic acid
  • 938-97-6
  • 4-Hydroxyphenylglycine
  • DL-4-Hydroxyphenylglycine
  • dl-p-Hydroxyphenylglycine
Molecular Weight
167.16 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-18
Description
4-hydroxyphenylglycine is a glycine molecule carrying a 4-hydroxyphenyl substituent. It has a role as a bacterial metabolite. It is functionally related to a glycine.
4-Hydroxyphenylglycine has been reported in Streptomyces fungicidicus with data available.
See also: D-4-Hydroxyphenylglycine (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
4-Hydroxyphenylglycine.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
H-DL-nTyr-OH
Sequence
X
HELM
PEPTIDE1{[c1cc(ccc1C(C(=O)O)N)O]}$$$$
IUPAC
DL-nortyrosine

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

2-amino-2-(4-hydroxyphenyl)acetic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

InChI=1S/C8H9NO3/c9-7(8(11)12)5-1-3-6(10)4-2-5/h1-4,7,10H,9H2,(H,11,12)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

LJCWONGJFPCTTL-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

C1=CC(=CC=C1C(C(=O)O)N)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C8H9NO3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

6324-01-2
37784-25-1
32462-30-9

3.3.2 European Community (EC) Number

3.3.3 UNII

3.3.4 ChEBI ID

3.3.5 DrugBank ID

3.3.6 DSSTox Substance ID

3.3.7 HMDB ID

3.3.8 Metabolomics Workbench ID

3.3.9 Nikkaji Number

3.3.10 NSC Number

3.3.11 Wikidata

3.3.12 Wikipedia

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • (R,S)-3HPG
  • 4-hydroxyphenylglycine
  • 4-hydroxyphenylglycine hydrobromide, (+-)-isomer
  • 4-hydroxyphenylglycine hydrochloride, (R)-isomer
  • 4-hydroxyphenylglycine perchlorate, (+-)-isomer
  • 4-hydroxyphenylglycine, (+-)-isomer
  • 4-hydroxyphenylglycine, (R)-isomer
  • 4-hydroxyphenylglycine, (S)-isomer
  • 4-hydroxyphenylglycine, 2,4-dimethylbenzenesulfonate, (+-)-isomer
  • 4-hydroxyphenylglycine, 2,4-dimethylbenzenesulfonate, (R)-isomer
  • 4-hydroxyphenylglycine, 4-methylbenzenesulfonate, (+-)-isomer
  • 4-hydroxyphenylglycine, 4-methylbenzenesulfonate, (S)-isomer
  • 4-hydroxyphenylglycine, monosodium salt
  • 4-hydroxyphenylglycine, monosodium salt, (R)-isomer
  • D-p-hydroxyphenylglycine
  • L-4-hydroxyphenylglycine
  • oxfenicine
  • p-hydroxyphenylglycine
  • UK 25842
  • UK-25842

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
167.16 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
-2.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
167.058243149 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
167.058243149 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
83.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
12
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
164
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
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 2021.10.14)

5 Spectral Information

5.1 1D NMR Spectra

5.1.1 13C NMR Spectra

Instrument Name
Varian CFT-20
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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5.2 Mass Spectrometry

5.2.1 GC-MS

1 of 2
NIST Number
238948
Library
Main library
Total Peaks
71
m/z Top Peak
122
m/z 2nd Highest
95
m/z 3rd Highest
77
Thumbnail
Thumbnail
2 of 2
Instrument Name
HP 6890 GC-5973
Source of Spectrum
SEP-40-SM1-1-1 (DOI: 10.1002/jssc.201700252)
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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5.2.2 Other MS

MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
166.051
Instrument
Orbitrap
Ionization Mode
negative
Top 5 Peaks

123.003204 100

79.012909 55.61

138.928375 42.67

122.023293 26.60

166.050278 25.89

Thumbnail
Thumbnail

5.3 IR Spectra

5.3.1 FTIR Spectra

1 of 2
Instrument Name
Bruker IFS 85
Technique
KBr-Pellet
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bruker IFS 85
Technique
KBr-Pellet
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
Thumbnail

7 Chemical Vendors

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Enzyme Inhibitors
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

9 Use and Manufacturing

9.1 General Manufacturing Information

EPA TSCA Commercial Activity Status
Benzeneacetic acid, .alpha.-amino-4-hydroxy-, (.alpha.S)-: INACTIVE

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Skin Irrit. 2 (100%)

Eye Irrit. 2 (100%)

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Thieme References

11.5 Chemical Co-Occurrences in Literature

11.6 Chemical-Gene Co-Occurrences in Literature

11.7 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Biological Test Results

13.1 BioAssay Results

14 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

15 Classification

15.1 MeSH Tree

15.2 ChEBI Ontology

15.3 ChemIDplus

15.4 ChEMBL Target Tree

15.5 UN GHS Classification

15.6 NORMAN Suspect List Exchange Classification

15.7 EPA DSSTox Classification

15.8 EPA TSCA and CDR Classification

15.9 LOTUS Tree

15.10 EPA Substance Registry Services Tree

15.11 MolGenie Organic Chemistry Ontology

16 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. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  4. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  5. EPA Chemicals under the TSCA
    Benzeneacetic acid, .alpha.-amino-4-hydroxy-, (.alpha.S)-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  6. EPA DSSTox
    Amino(4-hydroxyphenyl)acetic acid
    https://comptox.epa.gov/dashboard/DTXSID90860473
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  8. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  9. ChEBI
  10. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  11. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  12. Japan Chemical Substance Dictionary (Nikkaji)
  13. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  14. Metabolomics Workbench
  15. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    D-2-(4-Hydroxyphenyl)glycine
    http://www.nist.gov/srd/nist1a.cfm
  16. SpectraBase
    2-amino-2-(4-hydroxyphenyl)acetic acid
    https://spectrabase.com/spectrum/60n4NSRQGC3
  17. Springer Nature
  18. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  19. Wikidata
  20. Wikipedia
  21. PubChem
  22. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  23. GHS Classification (UNECE)
  24. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  25. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  26. EPA Substance Registry Services
  27. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  28. PATENTSCOPE (WIPO)
CONTENTS