Page last updated: 2024-12-07

5,6-dihydroxy-2-indolylcarboxylic acid

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

Description

5,6-dihydroxyindole-2-carboxylic acid : A dihydroxyindole that is indole-2-carboxylic acid substituted by hydroxy groups at positions 5 and 6. [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 CID119405
CHEMBL ID267855
CHEBI ID2003
SCHEMBL ID49512
MeSH IDM0096898

Synonyms (35)

Synonym
5,6-dihydroxy-1h-indole-2-carboxylic acid
1h-indole-2-carboxylic acid, 5,6-dihydroxy-
dhica
C04185
5,6-dihydroxyindole-2-carboxylic acid
dhi2c
CHEBI:2003 ,
4790-08-3
5,6-dihydroxy-2-indolylcarboxylic acid
5,6-dhica
5,6-dihydroxy-2-indolecarboxylic acid
CHEMBL267855 ,
FT-0667118
FT-0660760
AKOS006279100
1h-indole-2-carboxylicacid, 5,6-dihydroxy-
bdbm50420376
s6m6lzr326 ,
unii-s6m6lzr326
2-carboxy-5,6-dihydroxyindole
5,6-dihydroxy-2-carboxyindole
SCHEMBL49512
YFTGOBNOJKXZJC-UHFFFAOYSA-N
5,6-dihydroxy-1h-indole-2-carboxylicacid
mfcd02181103
DTXSID40197327
5,6-dihydroxy-2-indolylcarboxylate
5,6-dihydroxy-2-indolecarboxylate
Q5205021
DS-16518
AMY26927
SY114761
A918202
indole-2-carboxylic acid, 5,6-dihydroxy-
CS-W018944

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" We found that under the usual conditions of the biological assay, the apparent cytotoxicity of the two indoles reflect their instability in the culture medium, the less stable DHI being generally more toxic than DHICA to melanoma cells and nonmelanocytic cells."( The inherent cytotoxicity of melanin precursors: a revision.
Aroca, P; Hearing, VJ; Mascagna, D; Palumbo, A; Prota, G; Tsukamoto, K; Urabe, K, 1994
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[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 (1)

ClassDescription
dihydroxyindoleAny member of the class of hydroxyindoles carrying two hydroxy groups.
[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 (11)

PathwayProteinsCompounds
Tyrosine Metabolism1657
Alkaptonuria1657
Hawkinsinuria1657
Tyrosinemia Type I1657
Disulfiram Action Pathway2366
Tyrosinemia, Transient, of the Newborn1657
Dopamine beta-Hydroxylase Deficiency1657
Monoamine Oxidase-A Deficiency (MAO-A)1657
Eumelanin Biosynthesis29
GPR143 in melanocytes and retinal pigment epithelium cells713
Dopamine metabolism032

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Integrase Human immunodeficiency virus 1IC50 (µMol)10.00000.00051.544310.0000AID310941
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
G-protein coupled receptor 35Homo sapiens (human)EC50 (µMol)23.40000.00202.50079.8000AID683194; AID683195
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Processvia Protein(s)Taxonomy
cytoskeleton organizationG-protein coupled receptor 35Homo sapiens (human)
G protein-coupled receptor signaling pathwayG-protein coupled receptor 35Homo sapiens (human)
positive regulation of cytosolic calcium ion concentrationG-protein coupled receptor 35Homo sapiens (human)
chemokine-mediated signaling pathwayG-protein coupled receptor 35Homo sapiens (human)
negative regulation of voltage-gated calcium channel activityG-protein coupled receptor 35Homo sapiens (human)
negative regulation of neuronal action potentialG-protein coupled receptor 35Homo sapiens (human)
positive regulation of Rho protein signal transductionG-protein coupled receptor 35Homo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayG-protein coupled receptor 35Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
C-X-C chemokine receptor activityG-protein coupled receptor 35Homo sapiens (human)
G protein-coupled receptor activityG-protein coupled receptor 35Homo sapiens (human)
C-X-C chemokine receptor activityG-protein coupled receptor 35Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneG-protein coupled receptor 35Homo sapiens (human)
plasma membraneG-protein coupled receptor 35Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID683196Agonist activity at human GPR35 expressed in U2OS cells coexpressing Gal4-VP16/beta-arrestin fusion protein after 5 hrs by tango beta-arrestin translocation reporter gene assay relative to zaprinast2012ACS medicinal chemistry letters, Jul-12, Volume: 3, Issue:7
Synthesis and Agonistic Activity at the GPR35 of 5,6-Dihydroxyindole-2-carboxylic Acid Analogues.
AID310941Inhibition of HIV1 integrase2007European journal of medicinal chemistry, Sep, Volume: 42, Issue:9
Development of integrase inhibitors for treatment of AIDS: an overview.
AID683195Agonist activity at human GPR35 expressed in U2OS cells coexpressing Gal4-VP16/beta-arrestin fusion protein after 5 hrs by tango beta-arrestin translocation reporter gene assay2012ACS medicinal chemistry letters, Jul-12, Volume: 3, Issue:7
Synthesis and Agonistic Activity at the GPR35 of 5,6-Dihydroxyindole-2-carboxylic Acid Analogues.
AID683194Agonist activity at GPR35 in human HT-29 cells measured after 10 mins by dynamic mass redistribution assay2012ACS medicinal chemistry letters, Jul-12, Volume: 3, Issue:7
Synthesis and Agonistic Activity at the GPR35 of 5,6-Dihydroxyindole-2-carboxylic Acid Analogues.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (94)

TimeframeStudies, This Drug (%)All Drugs %
pre-199010 (10.64)18.7374
1990's42 (44.68)18.2507
2000's20 (21.28)29.6817
2010's21 (22.34)24.3611
2020's1 (1.06)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.29

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 Index10.29 (24.57)
Research Supply Index4.61 (2.92)
Research Growth Index4.89 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.29)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews4 (4.04%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other95 (95.96%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]