Page last updated: 2024-12-05

3-hydroxybenzeneacetic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

3-Hydroxybenzeneacetic acid, also known as m-hydroxyphenylacetic acid, is a naturally occurring aromatic compound found in various plants. It is synthesized through various pathways, including the shikimate pathway. This compound exhibits diverse biological activities, including antioxidant, anti-inflammatory, and antimicrobial properties. It has been investigated for its potential therapeutic applications in treating conditions such as cancer and Alzheimer's disease. Research focuses on its role in plant metabolism, its potential as a pharmaceutical agent, and its environmental impact. The compound's structural similarity to other phenolic compounds, its abundance in plants, and its biological activities make it a subject of ongoing scientific interest.'

3-hydroxybenzeneacetic acid: metabolite of L-dopa; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

3-hydroxyphenylacetic acid : A monocarboxylic acid that is phenylacetic acid in which the hydrogen at position 3 on the benzene ring is replaced by a hydroxy group. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID12122
CHEMBL ID190035
CHEBI ID17445
SCHEMBL ID337470
MeSH IDM0051619

Synonyms (67)

Synonym
CHEBI:17445 ,
m-hydroxyphenylacetic acid
inchi=1/c8h8o3/c9-7-3-1-2-6(4-7)5-8(10)11/h1-4,9h,5h2,(h,10,11
benzeneacetic acid, 3-hydroxy-
(3-hydroxyphenyl)acetic acid
3-hydroxybenzeneacetic acid
metahydroxy phenylacetic acid
nsc-14360
nsc14360
(m-hydroxyphenyl)acetic acid
acetic acid, (m-hydroxyphenyl)-
C05593
621-37-4
3-hydroxyphenylacetic acid
3-hydroxyphenylacetic acid, >=99%
3PCE
3HP ,
nsc 14360
einecs 210-684-4
acetic acid, 3-hydroxyphenyl-
91827D95-20B5-4654-B5F1-90598A532D49
2-(3-hydroxyphenyl)acetic acid
BMSE000339
benzeneacetic acid, 3-hydroxy- (9ci)
acetic acid, (m-hydroxyphenyl)- (8ci)
bdbm50168283
CHEMBL190035 ,
H0356
A8594
2-(3-hydroxyphenyl)acetic acid;3-hydroxyphenylacetic acid
AKOS005259462
2-(3-hydroxyphenyl)-acetic acid
3-hydroxyphenylaceticacid
EN300-54805
(3-hydroxy-phenyl)-acetic acid
S3364
AE-562/43460507
k59z6z8ref ,
unii-k59z6z8ref
FT-0615854
AM20061198
AB3840
BP-30187
SCHEMBL337470
hmdb00440
3'-hydroxyphenylacetic acid
PS-3166
SY013505
mfcd00004337
3-hydroxy phenylacetic acid
3-hydroxy-phenylacetic acid
3-hydroxy phenyl acetic acid
(3-hydroxy)phenylacetic acid
3-hydroxy-phenyl-acetic acid
3-hydroxy-phenyl acetic acid
3-hydroxyphenyl acetic acid
W-105043
AC-23554
DTXSID90211148
CS-W001083
3-hydroxy-benzeneacetic acid
3-hydroxy-benzeneacetate
(3-hydroxy-phenyl)-acetate
HY-W001083
Q10395566
Z816000338
PD098600

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" The aim of the current study was to characterize pharmacokinetic properties of DOPAC and 3-HPAA after intravenous bolus application in rats."( Single dose pharmacokinetics of intravenous 3,4-dihydroxyphenylacetic acid and 3-hydroxyphenylacetic acid in rats.
Butterweck, V; Hamburger, M; Oufir, M; Sampath, C; Zabela, V, 2020
)
0.56

Bioavailability

ExcerptReferenceRelevance
" However, the parent flavonoids have mostly low bioavailability and, hence, their metabolites have been hypothesized to be bioactive."( 3-Hydroxyphenylacetic Acid: A Blood Pressure-Reducing Flavonoid Metabolite.
Dias, P; Mladěnka, P; Nejmanová, I; Pourová, J; Vopršalová, M, 2022
)
0.72

Dosage Studied

ExcerptRelevanceReference
" dosing of TA-870 (30 mg/kg) were DA greater than homovanillic acid (HVA) greater than 3,4-dihydroxyphenylacetic acid (DOPAC) greater than 3-hydroxyphenylacetic acid (3-HPAC)."( Metabolism of a new orally active dopamine prodrug, N-(N-acetyl-L-methionyl)-O,O-bis(ethoxycarbonyl)dopamine (TA-870) and dopamine after oral administration to rats and dogs.
Endo, H; Komatsu, K; Sugawara, Y; Takaiti, O; Yoshikawa, M, 1990
)
0.28
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
human xenobiotic metaboliteAny human metabolite produced by metabolism of a xenobiotic compound in humans.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
monocarboxylic acidAn oxoacid containing a single carboxy group.
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (14)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, PROTOCATECHUATE 3,4-DIOXYGENASEPseudomonas putidaKi10,000.00004.00003,848.800010,000.0000AID977610
Chain M, PROTOCATECHUATE 3,4-DIOXYGENASEPseudomonas putidaKi10,000.00004.00003,848.800010,000.0000AID977610
Chain A, PROTOCATECHUATE 3,4-DIOXYGENASEPseudomonas putidaKi10,000.00004.00003,848.800010,000.0000AID977610
Chain M, PROTOCATECHUATE 3,4-DIOXYGENASEPseudomonas putidaKi10,000.00004.00003,848.800010,000.0000AID977610
Chain A, PROTOCATECHUATE 3,4-DIOXYGENASEPseudomonas putidaKi10,000.00004.00003,848.800010,000.0000AID977610
Chain M, PROTOCATECHUATE 3,4-DIOXYGENASEPseudomonas putidaKi10,000.00004.00003,848.800010,000.0000AID977610
Chain A, PROTOCATECHUATE 3,4-DIOXYGENASEPseudomonas putidaKi10,000.00004.00003,848.800010,000.0000AID977610
Chain M, PROTOCATECHUATE 3,4-DIOXYGENASEPseudomonas putidaKi10,000.00004.00003,848.800010,000.0000AID977610
Chain A, PROTOCATECHUATE 3,4-DIOXYGENASEPseudomonas putidaKi10,000.00004.00003,848.800010,000.0000AID977610
Chain M, PROTOCATECHUATE 3,4-DIOXYGENASEPseudomonas putidaKi10,000.00004.00003,848.800010,000.0000AID977610
Chain A, Protocatechuate 3,4-dioxygenasePseudomonas putidaKi10,000.00004.00003,848.800010,000.0000AID977610
Chain M, Protocatechuate 3,4-dioxygenasePseudomonas putidaKi10,000.00004.00003,848.800010,000.0000AID977610
Calcium/calmodulin-dependent protein kinase type II subunit alphaRattus norvegicus (Norway rat)IC50 (µMol)0.00010.00010.71098.4000AID1909935
Calcium/calmodulin-dependent protein kinase type II subunit alphaRattus norvegicus (Norway rat)Ki0.12590.02201.47405.1000AID1909935
TetraspaninRattus norvegicus (Norway rat)IC50 (µMol)12.00006.60006.60006.6000AID242222
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
cytosolCalcium/calmodulin-dependent protein kinase type II subunit alphaRattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID1909935Inhibition of [3H]NCS-382 binding to CaMK2alpha in rat cerebrocortical membranes
AID243773Percent displacement of [3H]GABA (1 mM) from Gamma-aminobutyric acid A receptor of rat cerebral cortex2005Bioorganic & medicinal chemistry letters, Jul-01, Volume: 15, Issue:13
Ethers of 3-hydroxyphenylacetic acid as selective gamma-hydroxybutyric acid receptor ligands.
AID1070390Cytotoxicity against mouse HT22 cells assessed as cell viability at 40 uM after 24 hrs by MTT assay2014Journal of natural products, Mar-28, Volume: 77, Issue:3
Flavonoids, flavonoid metabolites, and phenolic acids inhibit oxidative stress in the neuronal cell line HT-22 monitored by ECIS and MTT assay: a comparative study.
AID243735Percent displacement of [3H]GABA (1 mM) from Gamma-aminobutyric acid B receptor of rat cerebellum2005Bioorganic & medicinal chemistry letters, Jul-01, Volume: 15, Issue:13
Ethers of 3-hydroxyphenylacetic acid as selective gamma-hydroxybutyric acid receptor ligands.
AID242222Displacement of [3H]NCS-382 (16 nM) from GHB receptor of rat cerebrocortical membranes2005Bioorganic & medicinal chemistry letters, Jul-01, Volume: 15, Issue:13
Ethers of 3-hydroxyphenylacetic acid as selective gamma-hydroxybutyric acid receptor ligands.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB1997Biochemistry, Aug-19, Volume: 36, Issue:33
Structures of competitive inhibitor complexes of protocatechuate 3,4-dioxygenase: multiple exogenous ligand binding orientations within the active site.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (54)

TimeframeStudies, This Drug (%)All Drugs %
pre-199019 (35.19)18.7374
1990's7 (12.96)18.2507
2000's7 (12.96)29.6817
2010's12 (22.22)24.3611
2020's9 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.70

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.70 (24.57)
Research Supply Index4.06 (2.92)
Research Growth Index4.77 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.70)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (3.64%)5.53%
Reviews1 (1.82%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other52 (94.55%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]