Page last updated: 2024-12-06

squaric acid

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

Squaric acid is a dicarboxylic acid with the formula C4H2O4. It is a white, crystalline solid that is soluble in water. Squaric acid is a strong acid and has been used as a reagent in organic synthesis. It is also an important component of many pharmaceutical and industrial products. Squaric acid is an interesting molecule for its structural properties, being a highly conjugated and planar molecule with a square-shaped ring. The unique features of this acid make it an interesting target for study. The synthesis of squaric acid involves the reaction of acetylene with carbon dioxide in the presence of a catalyst. This reaction produces squaric acid, which is then purified by recrystallization. Squaric acid has been shown to exhibit a variety of biological effects, including antimicrobial, antiviral, and anticancer activity. These activities are related to the ability of squaric acid to inhibit certain enzymes and receptors. The ability of squaric acid to bind to proteins and nucleic acids has been studied extensively. Squaric acid is a highly versatile molecule and its unique features make it a subject of interest for many researchers. It is often used as a building block for the synthesis of novel materials and compounds with potential applications in various fields, such as medicine, materials science, and electronics. Studies of squaric acid are also important in the context of understanding the properties and reactivity of organic compounds.'

Cross-References

ID SourceID
PubMed CID17913
CHEBI ID52141
SCHEMBL ID56172
MeSH IDM0095353

Synonyms (81)

Synonym
2892-51-5
quadratic acid
wln: l4vvtj cq dq
3,2-dione
cyclobutenedione, dihydroxy-
nsc125692
nsc-125692
1,4-dihydroxycyclobutene
3-cyclobutene-1, 3,4-dihydroxy-
squaric acid ,
cyclobutene-1, 3,4-dihydroxy-
nsc-624671
nsc624671
3,4-dihydroxy-3-cyclobutene-1,2-dione
1,2-diketo-3,4-dihydroxycyclobutene
1,2-dihydroxycyclobutene-3,4-dione
ai3-61444
dihydroxycyclobutenedione
3,4-dihydroxy-cyclobutene-1,2-dione
brn 0774275
cyclobutene-1,2-dione, 3,4-dihydroxy-
nsc 125692
einecs 220-761-4
ccris 6793
1,2-dihydroxy cyclobutenedione
inchi=1/c4h2o4/c5-1-2(6)4(8)3(1)7/h5-6
3,4-dihydroxycyclobut-3-ene-1,2-dione
3-cyclobutene-1,2-dione, 3,4-dihydroxy-
3,4-dihydroxy-3-cyclobutene-1,2-dione, 99%
D1399
1-cyclobutene-3,4-dione-1,2-diol
AKOS000121580
1,2-dihydroxycyclobutenedione
quadratsaeure
svr9d0vodw ,
4-08-00-02701 (beilstein handbook reference)
3,4-dihydroxy-3-cyclobuten-1,2-dion [iupac]
unii-svr9d0vodw
3,4-dihydroxy-3-cyclobuten-1,2-dion
NCGC00260365-01
tox21_202819
dtxsid9049409 ,
dtxcid8029369
cas-2892-51-5
A819678
3,4-dihydroxycyclobut-3-ene-1,2-dione;3,4-dihydroxy-3-cyclobutene-1,2-dione
3,4-dihydroxy-cyclobut-3-ene-1,2-dione
BBL011240
STK936793
BP-10690
FT-0614321
1,2-dioxo-3,4-dihydroxycyclobut-3-ene
CHEBI:52141
1,2-dioxo-3,4-dihydroxycyclobutene
AM20090382
3-cyclobutene-1,2-dione,3,4-dihydroxy-
squaric acid [mi]
squaric acid [who-dd]
31150-56-8
SCHEMBL56172
dihydroxycyclobut-3-ene-1,2-dione
mfcd00001334
SY002206
1,2-dihydroxy-1-cyclobutene-3,4-dione
3,4-dihydroxy-3-cyclobuten-1,2-dione
1,2-dihydroxy-l-cyclobutene-3,4-dione
1,2-dihydroxy-3,4-cyclobutenedione
STR05257
1,2-dihydroxy-1-cyclobuten-3,4-dione
AC-22924
3,4-dihydroxy-3-cyclobutene-2-dione;quadratic acid
J-511200
3,4-dihydroxy-3-cyclobutene-1,2-dione, lonza quality, 98.50-101.00% (w/w) (hplc)
CS-W019969
nsc 624671
Z56347217
F0001-0904
Q3008466
Q903298
EN300-16613
SB11012

Research Excerpts

Overview

Squalic acid is an interesting small molecule with an almost perfectly square shape. Its analogues have a variety of biological activities that are enabled by the presence of significant H-bond donors and acceptors.

ExcerptReferenceRelevance
"Squaric acid is an interesting small molecule with an almost perfectly square shape, and its analogues have a variety of biological activities that are enabled by the presence of significant H-bond donors and acceptors."( Squaric acid analogues in medicinal chemistry.
Brulíková, L; Chasák, J; Šlachtová, V; Urban, M, 2021
)
2.79
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[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
carbon oxoacid
alicyclic ketoneA cyclic ketone in which the carbocyclic ring structure which may be saturated or unsaturated, but may not be a benzenoid or other aromatic system.
[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 (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AR proteinHomo sapiens (human)Potency24.36130.000221.22318,912.5098AID1259243; AID1259381
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency8.64370.001530.607315,848.9004AID1224841
estrogen nuclear receptor alphaHomo sapiens (human)Potency15.37090.000229.305416,493.5996AID1259244
thyroid stimulating hormone receptorHomo sapiens (human)Potency27.33380.001628.015177.1139AID1224843
Voltage-dependent calcium channel gamma-2 subunitMus musculus (house mouse)Potency15.37090.001557.789015,848.9004AID1259244
Glutamate receptor 2Rattus norvegicus (Norway rat)Potency15.37090.001551.739315,848.9004AID1259244
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGlutamate receptor 2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Research

Studies (93)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (4.30)18.7374
1990's3 (3.23)18.2507
2000's34 (36.56)29.6817
2010's41 (44.09)24.3611
2020's11 (11.83)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 50.46

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 Index50.46 (24.57)
Research Supply Index4.61 (2.92)
Research Growth Index5.44 (4.65)
Search Engine Demand Index85.47 (26.88)
Search Engine Supply Index2.20 (0.95)

This Compound (50.46)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.02%)5.53%
Reviews4 (4.08%)6.00%
Case Studies2 (2.04%)4.05%
Observational1 (1.02%)0.25%
Other90 (91.84%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]