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3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid

PubChem CID
102959
Structure
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid_small.png
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid_3D_Structure.png
Molecular Formula
Synonyms
  • 3247-75-4
  • 3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid
  • 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid
  • mHPHA
  • 3-(3-Hydroxyphenyl)-3-hydroxypropionic acid
Molecular Weight
182.17 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-18
Description
3-(3-hydroxyphenyl)-3-hydroxypropanoic acid is a dihydroxy monocarboxylic acid that is 3-hydroxypropanoic acid substituted by a 3-hydroxyphenyl group at position 3. It has a role as a human urinary metabolite. It is a member of phenols and a dihydroxy monocarboxylic acid. It is functionally related to a 3-hydroxypropionic acid.
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid has been reported in Homo sapiens with data available.
(3-Hydroxyphenyl)hydracrylate (HPHPA) is an organic acid detected in human urine. It is thought that the presence of this acid is from nutritional sources (i.e. dietary phenylalanine). However, there has been a considerable degree of ambiguity in the origin and/or significance of this compound (A15196). Recently it has been reported that HPHPA is actually an abnormal phenylalanine metabolite arising from bacterial metabolism in the gastrointestinal tract. Specifically HPHPA appears to arise from the action of the anaerobic bacteria Clostrida sp. (A15197). Elevated levels of HPHPA have been reported in the urine of children with autism as well as in adult patients with schizophrenia. It has been proposed that HPHPA may be a bacterial metabolite of m-tyrosine, a tyrosine analog that causes symptoms of autism in experimental animals.
A15196: Kumps A, Duez P, Mardens Y: Metabolic, nutritional, iatrogenic, and artifactual sources of urinary organic acids: a comprehensive table. Clin Chem. 2002 May;48(5):708-17. PMID:11978597
A15197: Shaw W: Increased urinary excretion of a 3-(3-hydroxyphenyl)-3-hydroxypropionic acid (HPHPA), an abnormal phenylalanine metabolite of Clostridia spp. in the gastrointestinal tract, in urine samples from patients with autism and schizophrenia. Nutr Neurosci. 2010 Jun;13(3):135-43. doi: 10.1179/147683010X12611460763968. PMID:20423563

1 Structures

1.1 2D Structure

Chemical Structure Depiction
3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-hydroxy-3-(3-hydroxyphenyl)propanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C9H10O4/c10-7-3-1-2-6(4-7)8(11)5-9(12)13/h1-4,8,10-11H,5H2,(H,12,13)
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

KHTAGVZHYUZYMF-UHFFFAOYSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

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

2.2 Molecular Formula

C9H10O4
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 UNII

2.3.3 ChEBI ID

2.3.4 DSSTox Substance ID

2.3.5 HMDB ID

2.3.6 Metabolomics Workbench ID

2.3.7 Nikkaji Number

2.3.8 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 3-(3-hydroxyphenyl)-3-hydroxypropanoic acid
  • 3-(3-hydroxyphenyl)-3-hydroxypropionic acid
  • beta-(meta-hydroxyphenyl)hydracrylic acid
  • HPHPA cpd
  • mHPHA

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
182.17 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3
Property Value
-0.4
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
182.05790880 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
182.05790880 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
77.8 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
13
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
180
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
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)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 4
View All
Spectra ID
Frequency
500 MHz
Solvent
H2O
Shifts [ppm]
6.84, 6.91, 5.03, 2.71, 2.64, 7.30, 6.97
Thumbnail
Thumbnail
2 of 4
View All
Spectra ID
Frequency
500 MHz
Solvent
H2O
Shifts [ppm]
6.84, 2.71, 5.03, 6.91, 2.64, 7.30, 6.97
Thumbnail
Thumbnail

4.2 2D NMR Spectra

4.2.1 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Varian
Frequency
500 MHz
Solvent
Water
pH
7.00
Shifts [ppm] (F2:F1):Intensity
7.22:130.48:0.41, 4.96:71.28:0.78, 6.75:114.79:0.35, 2.61:45.61:1.00, 6.89:118.15:0.35, 6.82:112.55:0.24
Thumbnail
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Biomarker Information

8 Food Additives and Ingredients

8.1 Associated Foods

9 Pharmacology and Biochemistry

9.1 Biochemical Reactions

10 Toxicity

10.1 Toxicological Information

10.1.1 Carcinogen Classification

Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

10.1.2 Health Effects

Chronically high levels of HPHPA is associated with autism and schizophrenia.

11 Associated Disorders and Diseases

Disease
Eosinophilic esophagitis
References
Mordechai, Hien, and David S. Wishart

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Chemical Co-Occurrences in Literature

12.5 Chemical-Gene Co-Occurrences in Literature

12.6 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Pathways

15 Taxonomy

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

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 ChemIDplus

16.4 NORMAN Suspect List Exchange Classification

16.5 EPA DSSTox Classification

16.6 LOTUS Tree

16.7 MolGenie Organic Chemistry Ontology

17 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/
    3-(3-Hydroxyphenyl)-3-hydroxypropionic acid
    https://commonchemistry.cas.org/detail?cas_rn=3247-75-4
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    3-Hydroxy-3-(3-hydroxyphenyl)propanoic acid
    https://comptox.epa.gov/dashboard/DTXSID00863132
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. 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
    3-(3-HYDROXYPHENYL)-3-HYDROXYPROPIONIC ACID
    https://gsrs.ncats.nih.gov/ginas/app/beta/substances/9IV9236GRD
  5. 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
    3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid
    http://www.hmdb.ca/metabolites/HMDB0002643
  6. ChEBI
    3-(3-hydroxyphenyl)-3-hydroxypropanoic acid
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:86369
  7. 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/
    3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid
    https://www.wikidata.org/wiki/Q27159109
  8. Toxin and Toxin Target Database (T3DB)
    LICENSE
    T3DB 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 (T3DB) and the original publication.
    http://www.t3db.ca/downloads
    3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid
    http://www.t3db.ca/toxins/T3D4966
  9. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
    3-(3-hydroxyphenyl)-3-hydroxypropanoic acid
    https://ctdbase.org/detail.go?type=chem&acc=C041797
  10. FooDB
    LICENSE
    FooDB 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 (FooDB) and the original publication.
    https://foodb.ca/about
    3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid
    https://foodb.ca/compounds/FDB023037
  11. Japan Chemical Substance Dictionary (Nikkaji)
  12. KNApSAcK Species-Metabolite Database
  13. Natural Product Activity and Species Source (NPASS)
  14. MarkerDB
    LICENSE
    This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
    https://markerdb.ca/
    3-(3-hydroxyphenyl)-3-hydroxypropanoic acid
    https://markerdb.ca/chemicals/850
  15. Metabolomics Workbench
  16. Springer Nature
  17. Wikidata
    3-(3-hydroxyphenyl)-3-hydroxypropionic acid
    https://www.wikidata.org/wiki/Q27159109
  18. PubChem
  19. 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
    3-(3-hydroxyphenyl)-3-hydroxypropanoic acid
    https://www.ncbi.nlm.nih.gov/mesh/67041797
  20. 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/
  21. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  22. PATENTSCOPE (WIPO)
CONTENTS