3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid
PubChem CID
102959
Structure
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
Chemical Structure Depiction
3-hydroxy-3-(3-hydroxyphenyl)propanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)
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)
KHTAGVZHYUZYMF-UHFFFAOYSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)
C1=CC(=CC(=C1)O)C(CC(=O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C9H10O4
Computed by PubChem 2.2 (PubChem release 2024.11.20)
- 3-(3-hydroxyphenyl)-3-hydroxypropanoic acid
- 3-(3-hydroxyphenyl)-3-hydroxypropionic acid
- beta-(meta-hydroxyphenyl)hydracrylic acid
- HPHPA cpd
- mHPHA
- 3247-75-4
- 3-(3-Hydroxyphenyl)-3-hydroxypropanoic acid
- 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid
- mHPHA
- 3-(3-Hydroxyphenyl)-3-hydroxypropionic acid
- HPHPA
- b-(m-Hydroxyphenyl)hydracrylic acid
- UNII-9IV9236GRD
- 9IV9236GRD
- 3'-Hydroxyphenylhydracrylic acid
- 3-Hydroxyphenyl-hydracrylic acid
- (3-Hydroxyphenyl)hydracrylic acid
- 3-(m-Hydroxyphenyl)hydracrylic acid
- 3-(3-Hydroxyphenyl)hydracrylic acid
- beta-(m-Hydroxyphenyl)hydracrylic acid
- Hydracrylic acid, 3-(m-hydroxyphenyl)-
- (3-Hydroxyphenyl)hydracrylate
- b-(m-Hydroxyphenyl)hydracrylate
- 3-(m-Hydroxyphenyl)hydracrylate
- 3-Hydroxy-3-(3-hydroxyphenyl)propionic acid
- 3-(3-Hydroxyphenyl)hydracrylate
- CHEBI:86369
- HMDB02643
- DTXSID00863132
- beta-(m-Hydroxyphenyl)hydracrylate
- 3-(3'-hydroxyphenyl)hydracrylic acid
- AG-F-08597
- 3-(3-hydroxyphenyl)-3-hydroxypropanoate
- 3-(3-Hydroxyphenyl)-3-hydroxypropionate
- .BETA.-M-HYDROXYPHENYLHYDRACRYLIC ACID
- HPHPA cpd
- Benzenepropanoic acid, b,3-dihydroxy-
- beta-(meta-Hydroxyphenyl)hydracrylic acid
- Benzenepropanoic acid, .beta.,3-dihydroxy-
- 3'-Hydroxyphenylhydracrylate
- 3-Hydroxyphenyl-hydracrylate
- SCHEMBL4957161
- DTXCID40811798
- 1-Chloro-4-fluoro-2-methyl-benzene
- beta, m-Dihydroxyphenylpropionic acid
- AKOS011682178
- beta, meta-Dihydroxyphenylpropionic acid
- 3-Hydroxy-3-(3-hydroxyphenyl)propionate
- Benzenepropanoic acid, beta,3-dihydroxy-
- PD165849
- BETA-M-HYDROXYPHENYLHYDRACRYLIC ACID
- 1ST163153
- 3-hydroxy-3-(3-hydroxyphenyl)propanoicacid
- DB-347510
- HY-113231
- A5957
- CS-0059368
- NS00075368
- 3-Hydroxy-3-(3'-hydroxyphenyl)propanoic acid
- 3-Hydroxy-3-(3'-hydroxyphenyl)propionic acid
- G92515
- .BETA.-(M-HYDROXYPHENYL)HYDRACRYLIC ACID
- EN300-1850114
- .BETA.-(META-HYDROXYPHENYL)HYDRACRYLIC ACID
- Q27159109
Property Name
Property Value
Reference
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)
Solid
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
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Stereo Count
Same Isotope Count
Same Parent, Connectivity Count
Same Parent, Stereo Count
Same Parent, Isotope Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).
Chronically high levels of HPHPA is associated with autism and schizophrenia.
Disease
References
Disease
Eosinophilic esophagitis
References
Mordechai, Hien, and David S. Wishart
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=KHTAGVZHYUZYMF-UHFFFAOYSA-N
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
- CAS Common ChemistryLICENSEThe 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 acidhttps://commonchemistry.cas.org/detail?cas_rn=3247-75-4
- ChemIDplus3-(3-Hydroxyphenyl)-3-hydroxypropanoic acidhttps://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0003247754ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- EPA DSSTox3-Hydroxy-3-(3-hydroxyphenyl)propanoic acidhttps://comptox.epa.gov/dashboard/DTXSID00863132CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- FDA Global Substance Registration System (GSRS)LICENSEUnless 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#linking3-(3-HYDROXYPHENYL)-3-HYDROXYPROPIONIC ACIDhttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/9IV9236GRD
- Human Metabolome Database (HMDB)LICENSEHMDB 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/citing3-(3-Hydroxyphenyl)-3-hydroxypropanoic acidhttp://www.hmdb.ca/metabolites/HMDB0002643HMDB0002643_nmr_one_166335https://hmdb.ca/metabolites/HMDB0002643#spectra
- ChEBI3-(3-hydroxyphenyl)-3-hydroxypropanoic acidhttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:86369
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/3-(3-Hydroxyphenyl)-3-hydroxypropanoic acidhttps://www.wikidata.org/wiki/Q27159109LOTUS Treehttps://lotus.naturalproducts.net/
- Toxin and Toxin Target Database (T3DB)LICENSET3DB 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/downloads3-(3-Hydroxyphenyl)-3-hydroxypropanoic acidhttp://www.t3db.ca/toxins/T3D4966
- Comparative Toxicogenomics Database (CTD)LICENSEIt 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.jsp3-(3-hydroxyphenyl)-3-hydroxypropanoic acidhttps://ctdbase.org/detail.go?type=chem&acc=C041797
- FooDBLICENSEFooDB 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/about3-(3-Hydroxyphenyl)-3-hydroxypropanoic acidhttps://foodb.ca/compounds/FDB023037
- Japan Chemical Substance Dictionary (Nikkaji)
- KNApSAcK Species-Metabolite Database
- Natural Product Activity and Species Source (NPASS)
- MarkerDBLICENSEThis work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.https://markerdb.ca/3-(3-hydroxyphenyl)-3-hydroxypropanoic acidhttps://markerdb.ca/chemicals/850
- Metabolomics Workbench3-(3-hydroxyphenyl)-3-hydroxypropanoic acidhttps://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=38184
- Springer Nature
- Wikidata3-(3-hydroxyphenyl)-3-hydroxypropionic acidhttps://www.wikidata.org/wiki/Q27159109
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks 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.html3-(3-hydroxyphenyl)-3-hydroxypropanoic acidhttps://www.ncbi.nlm.nih.gov/mesh/67041797
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/NORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 394795210https://pubchem.ncbi.nlm.nih.gov/substance/394795210
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