Compounds > calycopterin
Page last updated: 2024-11-12

calycopterin

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

Description

calycopterin: an immunoinhibitory compound from the extract of Dracocephalum kotschyi; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
Dracocephalumgenus[no description available]LamiaceaeThe mint plant family. They are characteristically aromatic, and many of them are cultivated for their oils. Most have square stems, opposite leaves, and two-lipped, open-mouthed, tubular corollas (united petals), with five-lobed, bell-like calyxes (united sepals).[MeSH]

Cross-References

ID SourceID
PubMed CID10429470
CHEMBL ID512767
CHEBI ID190878
SCHEMBL ID2214965
MeSH IDM0527725

Synonyms (16)

Synonym
CHEMBL512767
5,4'-dihydroxy-3,6,7,8-tetramethoxyflavone
LMPK12113311
calycopterin
481-52-7
5-hydroxy-2-(4-hydroxyphenyl)-3,6,7,8-tetramethoxychromen-4-one
5-hydroxy-2-(4-hydroxyphenyl)-3,6,7,8-tetramethoxy-4h-chromen-4-one
CHEBI:190878
SCHEMBL2214965
8794DO3YB5 ,
4h-1-benzopyran-4-one, 5-hydroxy-2-(4-hydroxyphenyl)-3,6,7,8-tetramethoxy-
calcycopterin
unii-8794do3yb5
Q27269811
DTXSID401317858
AKOS040734869

Research Excerpts

Overview

Calycopterin is a flavonoid isolated from Dracocephalum kotschyi. It has multiple medical uses, as an antispasmodic, analgesic, anti-hyperlipidemic, and immunomodulatory agents.

ExcerptReferenceRelevance
"Calycopterin is a flavonoid which was shown to induce preferential antiproliferative effects on some cancers; however, no information is available on its effect on breast cancer."( Flavonoid calycopterin triggers apoptosis in triple-negative and ER-positive human breast cancer cells through activating different patterns of gene expression.
Arefian, E; Attari, F; Delphi, L; Gholipour, H; Moradi, M; Moridi Farimani, M; Sepehri, H, 2020)		1.68
"Calycopterin is a flavonoid compound isolated from Dracocephalum kotschyi that has multiple medical uses, as an antispasmodic, analgesic, anti-hyperlipidemic, and immunomodulatory agents. "( Anticancer effect of calycopterin via PI3K/Akt and MAPK signaling pathways, ROS-mediated pathway and mitochondrial dysfunction in hepatoblastoma cancer (HepG2) cells.
Esmaeili, MA; Farimani, MM; Kiaei, M, 2014)		2.16

Treatment

ExcerptReferenceRelevance
"Calycopterin treatment also affected HepG2 cell viability: (a) by inhibiting cell cycle progression at the G2/M transition leading to growth arrest and apoptosis; (b) by decreasing the expression of mitotic kinase cdc2, mitotic phosphatase cdc25c, mitotic cyclin B1, and apoptotic factors pro-caspases-3 and -9; and (c) increasing the levels of mitochondrial apoptotic-related proteins, intracellular levels of reactive oxygen species, and nitric oxide."( Anticancer effect of calycopterin via PI3K/Akt and MAPK signaling pathways, ROS-mediated pathway and mitochondrial dysfunction in hepatoblastoma cancer (HepG2) cells.
Esmaeili, MA; Farimani, MM; Kiaei, M, 2014)		1.44

Pharmacokinetics

The plasma half-life for both agents was around 4 h, however, the volume of distribution of calycopterin appeared to be about 8 times greater than xanthomicrol.

ExcerptReferenceRelevance
"The plasma half-life for both agents was around 4 h, however, the volume of distribution of calycopterin appeared to be about 8 times greater than xanthomicrol."( Pharmacokinetics of calycopterin and xanthmicrol, two polymethoxylated hydroxyflavones with anti-angiogenic activities from Dracocephalum kotschyi Bioss.
Ebrahimi, SA; Etebari, M; Hossieni, M; Salehian, P; Zamani, SS, 2016)		0.98
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
etherAn organooxygen compound with formula ROR, where R is not hydrogen.
flavonoidsAny organic molecular entity whose stucture is based on derivatives of a phenyl-substituted 1-phenylpropane possessing a C15 or C16 skeleton, or such a structure which is condensed with a C6-C3 lignan precursors. The term is a 'superclass' comprising all members of the classes of flavonoid, isoflavonoid, neoflavonoid, chalcones, dihydrochalcones, aurones, pterocarpan, coumestans, rotenoid, flavonolignan, homoflavonoid and flavonoid oligomers. Originally restricted to natural products, the term is also applied to synthetic compounds related to them.
[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 (5)

Assay IDTitleYearJournalArticle
AID379313Antioxidant scavenging activity against 2,2'-azobis-amidinopropane-induced peroxyl radicals assessed as total oxyradical scavenging capacity2000Journal of natural products, Mar, Volume: 63, Issue:3
Evaluation of the total peroxyl radical-scavenging capacity of flavonoids: structure-activity relationships.
AID552377Cytotoxicity against human KB cells at 10'-6 M after 72 hrs by MTS assay2011Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1
Synthesis of antiproliferative flavones from calycopterin, major flavonoid of Calycopteris floribunda Lamk.
AID399171Trypanocidal activity against Trypanosoma cruzi Y strain trypomastigotes infected in Swiss albino mouse blood assessed as reduction of parasitemia at 1000 ug/mL after 24 hrs relative to control1997Journal of natural products, Aug, Volume: 60, Issue:8
Trypanocidal flavonoids from Trixis vauthieri.
AID552380Inhibition of sheep brain tubulin polymerization at 2x10'-5 M after 5 mins2011Bioorganic & medicinal chemistry, Jan-01, Volume: 19, Issue:1
Synthesis of antiproliferative flavones from calycopterin, major flavonoid of Calycopteris floribunda Lamk.
AID379312Antioxidant scavenging activity against 2,2'-azobis-amidinopropane-induced peroxyl radicals assessed as total oxyradical scavenging capacity relative to Trolox2000Journal of natural products, Mar, Volume: 63, Issue:3
Evaluation of the total peroxyl radical-scavenging capacity of flavonoids: structure-activity relationships.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (9.09)18.2507
2000's2 (18.18)29.6817
2010's6 (54.55)24.3611
2020's2 (18.18)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 13.01

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 Index13.01 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index5.50 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.01)

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%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
pyocyanine
Pyocyanine: Antibiotic pigment produced by Pseudomonas aeruginosa.. pyocyanine : An iminium betaine that is 5-methylphenazin-5-ium which is substituted at position 1 by an oxidanidyl group. An antibiotic pigment produced by Pseudomonas aeruginosa.		2.2510iminium betaine;
phenazines		antibacterial agent;
bacterial metabolite;
biological pigment;
virulence factor
gentian violet
Gentian Violet: A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties.. crystal violet : An organic chloride salt that is the monochloride salt of crystal violet cation. It has been used in creams for the topical treatment of bacterial and fungal infections, being effective against some Gram-positive bacteria (notably Staphylococcus species) and some pathogenic fungi (including Candida species) but use declined following reports of animal carcinogenicity. It has also been used for dying wood, silk, and paper, as well as a histological stain.		1.9910organic chloride saltanthelminthic drug;
antibacterial agent;
antifungal agent;
antiseptic drug;
histological dye
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid
[no description available]		210chromanol;
monocarboxylic acid;
phenols		antioxidant;
ferroptosis inhibitor;
neuroprotective agent;
radical scavenger;
Wnt signalling inhibitor
xanthomicrol
xanthomicrol: structure in first source. xanthomicrol : A trimethoxyflavone that is flavone substituted by methoxy groups at positions 6, 7 and 8 and hydroxy groups at positions 5 and 4'.		7.5220dihydroxyflavone;
trimethoxyflavone		antineoplastic agent;
plant metabolite
sakuranetin
sakuranetin: major rice phytoalexin; RN given for ((S)-(-))-isomer; structure in first source. sakuranetin : A flavonoid phytoalexin that is (S)-naringenin in which the hydroxy group at position 7 is replaced by a methoxy group.		1.9910(2S)-flavan-4-one;
4'-hydroxyflavanones;
dihydroxyflavanone;
flavonoid phytoalexin;
monomethoxyflavanone		antimycobacterial drug;
plant metabolite
4',5-dihydroxy-3',6,7,8-tetramethoxyflavone
[no description available]		210
5,3'-dihydroxy-3,6,7,8,4'-pentamethoxyflavone
5,3'-dihydroxy-3,6,7,8,4'-pentamethoxyflavone: an antineoplastic flavonol isolated from Polanisia dodecandra; structure given in first source		2.0610
quercetin
[no description available]		2107-hydroxyflavonol;
pentahydroxyflavone		antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
rutin
Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.		210disaccharide derivative;
quercetin O-glucoside;
rutinoside;
tetrahydroxyflavone		antioxidant;
metabolite
artemetin
[no description available]		210ether;
flavonoids
5,4'-dihydroxy-3,6,7-trimethoxyflavone
5,4'-dihydroxy-3,6,7-trimethoxyflavone: from Microliabum polymnioides; structure in first source		1.9910
fosbretabulin
[no description available]		2.0610stilbenoid
5-Hydroxyauranetin
5-hydroxy-3,6,7,8,4'-pentamethoxyflavone: has diuretic activity; isolated from Rubus rosaefolius		2.0610ether;
flavonoids
calpain
Calpain: Cysteine proteinase found in many tissues. Hydrolyzes a variety of endogenous proteins including NEUROPEPTIDES; CYTOSKELETAL PROTEINS; proteins from SMOOTH MUSCLE; CARDIAC MUSCLE; liver; platelets; and erythrocytes. Two subclasses having high and low calcium sensitivity are known. Removes Z-discs and M-lines from myofibrils. Activates phosphorylase kinase and cyclic nucleotide-independent protein kinase. This enzyme was formerly listed as EC 3.4.22.4.		2.0610
ConditionIndicatedRelationship StrengthStudiesTrials
ER-Negative PR-Negative HER2-Negative Breast Cancer
[description not available]		02.2510
Breast Cancer
[description not available]		07.2510
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.2510
Triple Negative Breast Neoplasms
Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.		02.2510
Cancer of Liver
[description not available]		02.110
Liver Neoplasms
Tumors or cancer of the LIVER.		02.110
Hepatoblastoma
A malignant neoplasm occurring in young children, primarily in the liver, composed of tissue resembling embryonal or fetal hepatic epithelium, or mixed epithelial and mesenchymal tissues. (Stedman, 25th ed)		07.110