Page last updated: 2024-12-04

homogentisic acid

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

Description

Homogentisic Acid: Dihydroxyphenylacetic acid with hydroxyls at the 2 and 5 positions of the phenyl ring. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

homogentisic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents at the 2- and 5-positions. [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 CID780
CHEBI ID44747
SCHEMBL ID155333
MeSH IDM0010517

Synonyms (66)

Synonym
benzeneacetic acid,5-dihydroxy-
alcapton
homogentisinic acid
nsc-88940
nsc88940
homogentisate acid
2,5-dihydroxy-.alpha.-toluic acid
acetic acid,5-dihydroxyphenyl)-
nsc 88940
brn 2692860
einecs 207-192-7
2,5-dihydroxybenzeneacetic acid
2,5-dihydroxy-alpha-toluic acid
benzeneacetic acid, 2,5-dihydroxy-
acetic acid, (2,5-dihydroxyphenyl)-
2-(2,5-dihydroxyphenyl)acetic acid
71694-00-3
2,5-dhpop
2-(3,6-dihydroxyphenyl)acetic acid
homogentisic acid
2,5-dihydroxyphenylacetic acid
2,5-dihydroxyphenylacetate
451-13-8
C00544
inchi=1/c8h8o4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10h,4h2,(h,11,12
CHEBI:44747
(2,5-dihydroxyphenyl)acetic acid
1AJP
homogentisic acid, crystalline
5A20D3D5-DF92-400D-AB62-07CC3E7DBFBB
D1050
DB08327
BMSE000200
1216468-48-2
FT-0669226
AKOS004910342
A826718
S9352
melanic acid
4-10-00-01506 (beilstein handbook reference)
np8ue6vf08 ,
unii-np8ue6vf08
homogentisic acid-13c6
FT-0610384
4AQ6
homogentisic acid [mi]
SCHEMBL155333
DTXSID1060005
W-109536
mfcd00004324
homogentisinate
2,5-dihydroxy-alpha-toluate
(2,5-dihydroxyphenyl)-acetate
2,5-dihydroxy-a-toluic acid
2,5-dihydroxy-a-toluate
(2,5-dihydroxyphenyl)-acetic acid
2,5-dihydroxy-benzeneacetate
CS-0059508
HY-113283
homogentisic acid, analytical standard
hq9 ,
Q416054
AS-19326
2-(2,5-dihydroxyphenyl)aceticacid
T70932
SY051598

Research Excerpts

Overview

Homogentisic acid (HGA) is a diagnostic metabolite that accumulates in the urine and tissues of patients with alkaptonuria which is a rare autosomal recessive disease.

ExcerptReferenceRelevance
"Homogentisic acid (HGA) is a diagnostic metabolite that accumulates in the urine and tissues of patients with alkaptonuria which is a rare autosomal recessive disease. "( Determination of homogentisic acid in urine for diagnosis of alcaptonuria: Capillary electrophoretic method optimization using experimental design.
Balta, GS; Cansever, MŞ; Öztekin, N, 2018
)
2.26

Effects

Homogentisic acid elevations have been found in urine and serum of patients on long term heavy salicylate therapy and those acutely intoxicated with acetylsalicylic acid.

ExcerptReferenceRelevance
"Homogentisic acid has very high antioxidant potential due to the presence of semiquinone structure."( DFT for exploring the antioxidant potential of homogentisic and orsellinic acids.
Iqbal, S; Mahmood, A; Naeem, S; Saqib, M, 2013
)
1.11
"Homogentisic acid elevations have been found in urine and serum of patients on long term heavy salicylate therapy and those acutely intoxicated with acetylsalicylic acid. "( Profiles in altered metabolism. II.--Accumulation of homogentisic acid in serum and urine following acetylsalicylic acid ingestion.
Mamer, OA; Montgomery, JA, 1978
)
1.95

Dosage Studied

ExcerptRelevanceReference
"05 mg bid, and remained on this dosage and a regular diet for 3 months."( Use of nitisinone in patients with alkaptonuria.
Bernardini, I; Gahl, WA; Gerber, LH; Kaiser-Kupfer, MI; O'Brien, K; Perry, MB; Rubin, BI; Sebring, N; Suwannarat, P; Tsilou, E, 2005
)
0.33
" Nitisinone decreases homogentisic acid (HGA) in AKU but the dose-response relationship has not been previously studied."( Suitability Of Nitisinone In Alkaptonuria 1 (SONIA 1): an international, multicentre, randomised, open-label, no-treatment controlled, parallel-group, dose-response study to investigate the effect of once daily nitisinone on 24-h urinary homogentisic acid
Ayoob, H; Braconi, D; Briggs, MC; Bygott, H; Christensen, P; Cox, TF; Cronlund, A; Dutton, JJ; Fitzgerald, R; Gallagher, JA; Genovese, F; Hall, AK; Hughes, AT; Imrich, R; Jarvis, JC; Junestrand, C; Kullenberg, T; Laan, D; Le Quan Sang, KH; McCaffrey, J; Milan, AM; Nemethova, M; Olsson, B; Psarelli, EE; Ranganath, LR; Ross, G; Rovensky, J; Rudebeck, M; Santucci, A; Sireau, N; Svensson, L; Szamosi, J; Timmis, OG; van Kan, C; Zatkova, A, 2016
)
0.93
"Suitability Of Nitisinone In Alkaptonuria 1 (SONIA 1) was an international, multicentre, randomised, open-label, no-treatment controlled, parallel-group, dose-response study."( Suitability Of Nitisinone In Alkaptonuria 1 (SONIA 1): an international, multicentre, randomised, open-label, no-treatment controlled, parallel-group, dose-response study to investigate the effect of once daily nitisinone on 24-h urinary homogentisic acid
Ayoob, H; Braconi, D; Briggs, MC; Bygott, H; Christensen, P; Cox, TF; Cronlund, A; Dutton, JJ; Fitzgerald, R; Gallagher, JA; Genovese, F; Hall, AK; Hughes, AT; Imrich, R; Jarvis, JC; Junestrand, C; Kullenberg, T; Laan, D; Le Quan Sang, KH; McCaffrey, J; Milan, AM; Nemethova, M; Olsson, B; Psarelli, EE; Ranganath, LR; Ross, G; Rovensky, J; Rudebeck, M; Santucci, A; Sireau, N; Svensson, L; Szamosi, J; Timmis, OG; van Kan, C; Zatkova, A, 2016
)
0.62
"A clear dose-response relationship was observed between nitisinone and the urinary excretion of HGA."( Suitability Of Nitisinone In Alkaptonuria 1 (SONIA 1): an international, multicentre, randomised, open-label, no-treatment controlled, parallel-group, dose-response study to investigate the effect of once daily nitisinone on 24-h urinary homogentisic acid
Ayoob, H; Braconi, D; Briggs, MC; Bygott, H; Christensen, P; Cox, TF; Cronlund, A; Dutton, JJ; Fitzgerald, R; Gallagher, JA; Genovese, F; Hall, AK; Hughes, AT; Imrich, R; Jarvis, JC; Junestrand, C; Kullenberg, T; Laan, D; Le Quan Sang, KH; McCaffrey, J; Milan, AM; Nemethova, M; Olsson, B; Psarelli, EE; Ranganath, LR; Ross, G; Rovensky, J; Rudebeck, M; Santucci, A; Sireau, N; Svensson, L; Szamosi, J; Timmis, OG; van Kan, C; Zatkova, A, 2016
)
0.62
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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
dihydroxyphenylacetic acidA dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.
hydroquinonesBenzenediols that have the hydroxy substituents in the 1- and 4-positions.
[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]

Pathways (15)

PathwayProteinsCompounds
Tyrosine Metabolism1657
Phenylalanine and Tyrosine Metabolism1121
Phenylketonuria1121
Tyrosinemia Type 2 (or Richner-Hanhart Syndrome)1121
Tyrosinemia Type 3 (TYRO3)1121
Alkaptonuria1657
Hawkinsinuria1657
Tyrosinemia Type I1657
Disulfiram Action Pathway2366
Tyrosinemia, Transient, of the Newborn1657
Dopamine beta-Hydroxylase Deficiency1657
Monoamine Oxidase-A Deficiency (MAO-A)1657
Plastoquinol-9 Biosynthesis616
Tyrosine metabolism ( Tyrosine metabolism )2841
Biochemical pathways: part I0466

Protein Targets (14)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Penicillin AmidohydrolaseEscherichia coliKi5,850.000082.00002,297.80005,850.0000AID977610
Chain B, Penicillin AmidohydrolaseEscherichia coliKi5,850.000082.00002,297.80005,850.0000AID977610
Chain A, Penicillin AmidohydrolaseEscherichia coliKi5,850.000082.00002,297.80005,850.0000AID977610
Chain B, Penicillin AmidohydrolaseEscherichia coliKi5,850.000082.00002,297.80005,850.0000AID977610
Chain A, Penicillin AmidohydrolaseEscherichia coliKi5,850.000082.00002,297.80005,850.0000AID977610
Chain B, Penicillin AmidohydrolaseEscherichia coliKi5,850.000082.00002,297.80005,850.0000AID977610
Chain A, Penicillin AmidohydrolaseEscherichia coliKi5,850.000082.00002,297.80005,850.0000AID977610
Chain B, Penicillin AmidohydrolaseEscherichia coliKi5,850.000082.00002,297.80005,850.0000AID977610
Chain A, Penicillin AmidohydrolaseEscherichia coliKi5,850.000082.00002,297.80005,850.0000AID977610
Chain B, Penicillin AmidohydrolaseEscherichia coliKi5,850.000082.00002,297.80005,850.0000AID977610
Chain A, Penicillin AmidohydrolaseEscherichia coliKi5,850.000082.00002,297.80005,850.0000AID977610
Chain B, Penicillin AmidohydrolaseEscherichia coliKi5,850.000082.00002,297.80005,850.0000AID977610
Chain A, Penicillin AmidohydrolaseEscherichia coliKi5,850.000082.00002,297.80005,850.0000AID977610
Chain B, Penicillin AmidohydrolaseEscherichia coliKi5,850.000082.00002,297.80005,850.0000AID977610
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2013Proceedings of the National Academy of Sciences of the United States of America, Jul-30, Volume: 110, Issue:31
Visualizing the substrate-, superoxo-, alkylperoxo-, and product-bound states at the nonheme Fe(II) site of homogentisate dioxygenase.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB1998Journal of molecular biology, Nov-27, Volume: 284, Issue:2
Ligand-induced conformational change in penicillin acylase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (387)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990152 (39.28)18.7374
1990's34 (8.79)18.2507
2000's62 (16.02)29.6817
2010's89 (23.00)24.3611
2020's50 (12.92)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 57.99

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index57.99 (24.57)
Research Supply Index6.02 (2.92)
Research Growth Index4.71 (4.65)
Search Engine Demand Index95.63 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (57.99)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (1.23%)5.53%
Reviews31 (7.64%)6.00%
Case Studies86 (21.18%)4.05%
Observational0 (0.00%)0.25%
Other284 (69.95%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]