Page last updated: 2024-12-11

sappanchalcone

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

Description

sappanchalcone: RN given from Toxline; RN not in Chemline 3/85; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

sappanchalcone : A member of the class of chalcones that consists of trans-chalcone substituted by hydroxy groups at positions 3, 4 and 4' and a methoxy group at position 2'. Isolated from Caesalpinia sappan, it exhibits neuroprotective and cytoprotective activity. [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]

FloraRankFlora DefinitionFamilyFamily Definition
CaesalpiniagenusA plant genus of the family FABACEAE. The common name of Bird-Of-Paradise is also used for other plants such as Heliconia (HELICONIACEAE) and Strelitzia (STRELITZIACEAE) and some birds. The common name of Cat's-Claw is more often used with UNCARIA. The common name of Pernambuco also refers to a state in Brazil. Furanoditerpenoid lactones and caesalpin are produced by members of this genus.[MeSH]FabaceaeThe large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]
Caesalpinia sappanspecies[no description available]FabaceaeThe large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]

Cross-References

ID SourceID
PubMed CID5319493
CHEMBL ID476986
CHEBI ID66172
SCHEMBL ID2835459
MeSH IDM0129676

Synonyms (18)

Synonym
sappanchalcone
LMPK12120114
chebi:66172 ,
CHEMBL476986
(e)-3-(3,4-dihydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl)prop-2-en-1-one
94344-54-4
2-propen-1-one, 3-(3,4-dihydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl)-, (e)-
(2e)-3-(3,4-dihydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl)prop-2-en-1-one
3,4,4'-trihydroxy-2'-methoxychalcone
AKOS022186153
SCHEMBL2835459
2-propen-1-one,3-(3,4-dihydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl)-, (2e)-
(e)-3-(3,4-dihydroxyphenyl)-1-(4-hydroxy-2-methoxy-phenyl)prop-2-en-1-one
Q27134703
MS-24086
DTXSID501317382
CS-0006526
HY-59001

Research Excerpts

Effects

ExcerptReferenceRelevance
"Sappanchalcone has been demonstrated to possess several biological effects. "( Effects of sappanchalcone on the cytoprotection and anti-inflammation via heme oxygenase-1 in human pulp and periodontal ligament cells.
Jeong, GS; Kim, EC; Kim, YC; Lee, DS; Lee, HJ; Li, B, 2010
)
2.19

Actions

ExcerptReferenceRelevance
"Sappanchalcone is seen to inhibit LPS-stimulated nitric oxide (NO), prostaglandin E(2) (PGE(2)), interlukine-1beta (IL-1beta), tumor necrosis factor-alpha (TNF-alpha), interlukine-6 (IL-6) and interlukine-12 (IL-12) release in addition to inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) expression in HPDL cells."( Effects of sappanchalcone on the cytoprotection and anti-inflammation via heme oxygenase-1 in human pulp and periodontal ligament cells.
Jeong, GS; Kim, EC; Kim, YC; Lee, DS; Lee, HJ; Li, B, 2010
)
1.47

Treatment

ExcerptReferenceRelevance
"Sappanchalcone-treated oral cancer cells showed an increased cytosolic level of cytochrome c, downregulated Bcl-2 expression, upregulated Bax and p53 expression, caspase-3 and -9 activation, and poly (ADP-ribose) polymerase cleavage."( Mechanism of sappanchalcone-induced growth inhibition and apoptosis in human oral cancer cells.
Choi, BJ; Kim, EC; Kim, YC; Lee, DW; Lee, YM; Yoon, JH, 2011
)
1.46
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antioxidantA substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
anti-inflammatory agentAny compound that has anti-inflammatory effects.
anti-allergic agentA drug used to treat allergic reactions.
[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 (3)

ClassDescription
chalconesA ketone that is 1,3-diphenylpropenone (benzylideneacetophenone), ArCH=CH(=O)Ar, and its derivatives formed by substitution.
catecholsAny compound containing an o-diphenol component.
monomethoxybenzeneCompounds containing a benzene skeleton substituted with one methoxy group.
[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]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID456318DPPH radical scavenging activity assessed as trolox equivalent antioxidant capacity2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids.
AID1737995Inhibition of LPS stimulated TNF alpha production in Balb/c mouse peritoneal macrophages measured by ELISA plate reader method2020European journal of medicinal chemistry, Jul-01, Volume: 197Synthesis and evaluation of butein derivatives for in vitro and in vivo inflammatory response suppression in lymphedema.
AID341705Inhibition of c-Src at 10 uM by ELISA2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Naturally occurring homoisoflavonoids function as potent protein tyrosine kinase inhibitors by c-Src-based high-throughput screening.
AID341709Inhibition of KDR at 10 uM by ELISA2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Naturally occurring homoisoflavonoids function as potent protein tyrosine kinase inhibitors by c-Src-based high-throughput screening.
AID456316ABTS radical scavenging activity assessed as trolox equivalent antioxidant capacity2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids.
AID341706Inhibition of c-Met at 10 uM by ELISA2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Naturally occurring homoisoflavonoids function as potent protein tyrosine kinase inhibitors by c-Src-based high-throughput screening.
AID341707Inhibition of FGFR1 at 10 uM by ELISA2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Naturally occurring homoisoflavonoids function as potent protein tyrosine kinase inhibitors by c-Src-based high-throughput screening.
AID341713Inhibition of cKit at 10 uM by ELISA2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Naturally occurring homoisoflavonoids function as potent protein tyrosine kinase inhibitors by c-Src-based high-throughput screening.
AID341720Inhibition of FGFR2 at 10 uM by ELISA2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Naturally occurring homoisoflavonoids function as potent protein tyrosine kinase inhibitors by c-Src-based high-throughput screening.
AID341711Inhibition of EGFR at 10 uM by ELISA2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Naturally occurring homoisoflavonoids function as potent protein tyrosine kinase inhibitors by c-Src-based high-throughput screening.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (5.56)18.7374
1990's0 (0.00)18.2507
2000's4 (22.22)29.6817
2010's10 (55.56)24.3611
2020's3 (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: 16.55

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index16.55 (24.57)
Research Supply Index2.94 (2.92)
Research Growth Index4.31 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (16.55)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other18 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]