Compounds > hydroxygenkwanin
Page last updated: 2024-11-11

hydroxygenkwanin

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

Description

hydroxygenkwanin: isolated from leaves of Daphne genkwa [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
DaphnegenusA plant genus of the family THYMELAEACEAE. They are evergreen shrubs much cultivated in garden borders and rock gardens in mild climates. Members contain mezerein, flavonoids, and COUMARINS such as daphnetin and daphnin.[MeSH]ThymelaeaceaeA plant family of the order Myrtales, subclass Rosidae, class Magnoliopsida. They are mainly trees and shrubs. Many members contain mucilage and COUMARINS.[MeSH]
Daphne genkwaspecies[no description available]ThymelaeaceaeA plant family of the order Myrtales, subclass Rosidae, class Magnoliopsida. They are mainly trees and shrubs. Many members contain mucilage and COUMARINS.[MeSH]

Cross-References

ID SourceID
PubMed CID5318214
CHEMBL ID183745
CHEBI ID168675
SCHEMBL ID4203893
MeSH IDM0146367

Synonyms (36)

Synonym
2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxychromen-4-one
20243-59-8
CHEBI:168675
2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-chromen-4-one
4h-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-
hydroxygenkwanin
MEGXP0_000798
ACON1_000842
NCGC00169305-01
2-(3,4-dihydroxy-phenyl)-5-hydroxy-7-methoxy-chromen-4-one
2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4h-chromen-4-one
bdbm50240943
CHEMBL183745 ,
LMPK12111045
luteolin 7-methyl ether
5,3',4'-trihydroxy-7-methoxyflavone
7-o-methylluteolin
unii-732ga1z079
732ga1z079 ,
S9205
AKOS015999029
SCHEMBL4203893
3'-hydroxygenkwanin
FT-0697965
2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4h-1-benzopyran-4-one, 9ci
2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4h-1-benzopyran-4-one
2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4h-1-chromen-4-one
6B5 ,
CS-0016871
HY-N1438
CCG-267462
Q27266123
A879764
4h-1-benzopyran-4-one,2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-
MS-24321
AC-34593

Research Excerpts

Effects

ExcerptReferenceRelevance
"Hydroxygenkwanin (HGK) has an anticancer effect in a variety of tumors, but its role in osteosarcoma has not been explored. "( Hydroxygenkwanin suppresses proliferation, invasion and migration of osteosarcoma cells via the miR‑320a/SOX9 axis.
An, G; Dong, X; Wang, Y; Zhuang, H, 2022)		3.61
"Hydroxygenkwanin (HGK) has an anticancer effect in a variety of tumors, but its role in osteosarcoma has not been explored. "( Hydroxygenkwanin suppresses proliferation, invasion and migration of osteosarcoma cells via the miR‑320a/SOX9 axis.
An, G; Dong, X; Wang, Y; Zhuang, H, 2022)		3.61
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
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.
etherAn organooxygen compound with formula ROR, where R is not hydrogen.
[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 (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
PlasminogenHomo sapiens (human)IC50 (µMol)2.30000.02503.628010.0000AID378554
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (19)

Processvia Protein(s)Taxonomy
proteolysisPlasminogenHomo sapiens (human)
blood coagulationPlasminogenHomo sapiens (human)
negative regulation of cell population proliferationPlasminogenHomo sapiens (human)
negative regulation of cell-substrate adhesionPlasminogenHomo sapiens (human)
extracellular matrix disassemblyPlasminogenHomo sapiens (human)
tissue regenerationPlasminogenHomo sapiens (human)
fibrinolysisPlasminogenHomo sapiens (human)
positive regulation of blood vessel endothelial cell migrationPlasminogenHomo sapiens (human)
myoblast differentiationPlasminogenHomo sapiens (human)
muscle cell cellular homeostasisPlasminogenHomo sapiens (human)
tissue remodelingPlasminogenHomo sapiens (human)
biological process involved in interaction with symbiontPlasminogenHomo sapiens (human)
negative regulation of fibrinolysisPlasminogenHomo sapiens (human)
positive regulation of fibrinolysisPlasminogenHomo sapiens (human)
trophoblast giant cell differentiationPlasminogenHomo sapiens (human)
labyrinthine layer blood vessel developmentPlasminogenHomo sapiens (human)
mononuclear cell migrationPlasminogenHomo sapiens (human)
trans-synaptic signaling by BDNF, modulating synaptic transmissionPlasminogenHomo sapiens (human)
negative regulation of cell-cell adhesion mediated by cadherinPlasminogenHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
protease bindingPlasminogenHomo sapiens (human)
endopeptidase activityPlasminogenHomo sapiens (human)
serine-type endopeptidase activityPlasminogenHomo sapiens (human)
signaling receptor bindingPlasminogenHomo sapiens (human)
protein bindingPlasminogenHomo sapiens (human)
serine-type peptidase activityPlasminogenHomo sapiens (human)
enzyme bindingPlasminogenHomo sapiens (human)
kinase bindingPlasminogenHomo sapiens (human)
protein domain specific bindingPlasminogenHomo sapiens (human)
apolipoprotein bindingPlasminogenHomo sapiens (human)
protein-folding chaperone bindingPlasminogenHomo sapiens (human)
protein antigen bindingPlasminogenHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
extracellular regionPlasminogenHomo sapiens (human)
extracellular spacePlasminogenHomo sapiens (human)
plasma membranePlasminogenHomo sapiens (human)
external side of plasma membranePlasminogenHomo sapiens (human)
cell surfacePlasminogenHomo sapiens (human)
platelet alpha granule lumenPlasminogenHomo sapiens (human)
collagen-containing extracellular matrixPlasminogenHomo sapiens (human)
extracellular exosomePlasminogenHomo sapiens (human)
blood microparticlePlasminogenHomo sapiens (human)
Schaffer collateral - CA1 synapsePlasminogenHomo sapiens (human)
glutamatergic synapsePlasminogenHomo sapiens (human)
extracellular spacePlasminogenHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID1498430Inhibition of melanogenesis in mouse B16 cells assessed as intracellular melanogenesis activity at 12.5 uM after 72 hrs relative to control2018Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14
Selective synthesis of 7-O-substituted luteolin derivatives and their melanonenesis and proliferation inhibitory activity in B16 melanoma cells.
AID1498429Inhibition of melanogenesis in mouse B16 cells assessed as intracellular melanogenesis activity at 25 uM after 72 hrs relative to control2018Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14
Selective synthesis of 7-O-substituted luteolin derivatives and their melanonenesis and proliferation inhibitory activity in B16 melanoma cells.
AID1498425Antiproliferative activity against mouse B16 cells assessed as cell proliferation level at 12.5 uM after 72 hrs by MTT assay relative to control2018Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14
Selective synthesis of 7-O-substituted luteolin derivatives and their melanonenesis and proliferation inhibitory activity in B16 melanoma cells.
AID253264Ratio between antioxidant activities determined employing ABTS and DPPH methods2005Bioorganic & medicinal chemistry letters, Jan-17, Volume: 15, Issue:2
Structure-antioxidant activity relationships of flavonoids isolated from the resinous exudate of Heliotropium sinuatum.
AID1498436Inhibition of melanogenesis in mouse B16 cells assessed as extracellular melanogenesis activity at 6.25 uM after 72 hrs relative to control2018Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14
Selective synthesis of 7-O-substituted luteolin derivatives and their melanonenesis and proliferation inhibitory activity in B16 melanoma cells.
AID1498426Antiproliferative activity against mouse B16 cells assessed as cell proliferation level at 6.25 uM after 72 hrs by MTT assay relative to control2018Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14
Selective synthesis of 7-O-substituted luteolin derivatives and their melanonenesis and proliferation inhibitory activity in B16 melanoma cells.
AID1498434Inhibition of melanogenesis in mouse B16 cells assessed as extracellular melanogenesis activity at 25 uM after 72 hrs relative to control2018Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14
Selective synthesis of 7-O-substituted luteolin derivatives and their melanonenesis and proliferation inhibitory activity in B16 melanoma cells.
AID1498435Inhibition of melanogenesis in mouse B16 cells assessed as extracellular melanogenesis activity at 12.5 uM after 72 hrs relative to control2018Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14
Selective synthesis of 7-O-substituted luteolin derivatives and their melanonenesis and proliferation inhibitory activity in B16 melanoma cells.
AID1498424Antiproliferative activity against mouse B16 cells assessed as cell proliferation level at 25 uM after 72 hrs by MTT assay relative to control2018Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14
Selective synthesis of 7-O-substituted luteolin derivatives and their melanonenesis and proliferation inhibitory activity in B16 melanoma cells.
AID1498428Inhibition of melanogenesis in mouse B16 cells assessed as intracellular melanogenesis activity at 50 uM after 72 hrs relative to control2018Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14
Selective synthesis of 7-O-substituted luteolin derivatives and their melanonenesis and proliferation inhibitory activity in B16 melanoma cells.
AID1498431Inhibition of melanogenesis in mouse B16 cells assessed as intracellular melanogenesis activity at 6.25 uM after 72 hrs relative to control2018Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14
Selective synthesis of 7-O-substituted luteolin derivatives and their melanonenesis and proliferation inhibitory activity in B16 melanoma cells.
AID1498423Antiproliferative activity against mouse B16 cells assessed as cell proliferation level at 50 uM after 72 hrs by MTT assay relative to control2018Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14
Selective synthesis of 7-O-substituted luteolin derivatives and their melanonenesis and proliferation inhibitory activity in B16 melanoma cells.
AID378554Inhibition of plasmin2005Journal of natural products, Mar, Volume: 68, Issue:3
Sesquiterpenoids and plasmin-inhibitory flavonoids from Blumea balsamifera.
AID1498433Inhibition of melanogenesis in mouse B16 cells assessed as extracellular melanogenesis activity at 50 uM after 72 hrs relative to control2018Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14
Selective synthesis of 7-O-substituted luteolin derivatives and their melanonenesis and proliferation inhibitory activity in B16 melanoma cells.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (20)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (10.00)18.7374
1990's0 (0.00)18.2507
2000's4 (20.00)29.6817
2010's9 (45.00)24.3611
2020's5 (25.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.40

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 Index23.40 (24.57)
Research Supply Index3.04 (2.92)
Research Growth Index4.81 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.40)

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%
Other20 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
4-hydroxybenzoic acid
4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.		2.0510monohydroxybenzoic acidalgal metabolite;
plant metabolite
acetic acid
Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.		2.5420monocarboxylic acidantimicrobial food preservative;
Daphnia magna metabolite;
food acidity regulator;
protic solvent
4-nitrophenol
4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.		2.13104-nitrophenolshuman xenobiotic metabolite;
mouse metabolite
palmitic acid
Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.		2.0510long-chain fatty acid;
straight-chain saturated fatty acid		algal metabolite;
Daphnia magna metabolite;
EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor;
plant metabolite
propylparaben
Parabens: Methyl, propyl, butyl, and ethyl esters of p-hydroxybenzoic acid. They have been approved by the FDA as antimicrobial agents for foods and pharmaceuticals. (From Hawley's Condensed Chemical Dictionary, 11th ed, p872)		2.0510benzoate ester;
paraben;
phenols		antifungal agent;
antimicrobial agent
diphenhydramine hydrochloride
Antitussive Agents: Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally.. diphenhydramine hydrochloride : The hydrochloride salt of diphenhydramine.		1.9610hydrochloride;
organoammonium salt		anti-allergic agent;
antiemetic;
antiparkinson drug;
antipruritic drug;
H1-receptor antagonist;
local anaesthetic;
muscarinic antagonist;
sedative
leupeptin
[no description available]		2.0210aldehyde;
tripeptide		bacterial metabolite;
calpain inhibitor;
cathepsin B inhibitor;
EC 3.4.21.4 (trypsin) inhibitor;
serine protease inhibitor
genkwadaphnin
genkwadaphnin: from Daphne genkwa; structure given in first source		2.1710
arbutin
hydroquinone O-beta-D-glucopyranoside : A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.		2.1710beta-D-glucoside;
monosaccharide derivative		Escherichia coli metabolite;
plant metabolite
gamma-sitosterol
clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.		2.05103beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
phytosterols		marine metabolite;
plant metabolite
cytellin
cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982		2.0510
3,7-dimethoxy-5,3',4'-trihydroxyflavone
3,7-dimethoxy-5,3',4'-trihydroxyflavone: isolated from Veronia eremophila; structure given in first source. 3',4',5-trihydroxy-3,7-dimethoxyflavone : A dimethoxyflavone that the 3,7-di-O-methyl derivative of quercetin.		2.0210dimethoxyflavone;
trihydroxyflavone		EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor;
metabolite
apigenin
Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.		8.0340trihydroxyflavoneantineoplastic agent;
metabolite
luteolin
[no description available]		2.85303'-hydroxyflavonoid;
tetrahydroxyflavone		angiogenesis inhibitor;
anti-inflammatory agent;
antineoplastic agent;
apoptosis inducer;
c-Jun N-terminal kinase inhibitor;
EC 2.3.1.85 (fatty acid synthase) inhibitor;
immunomodulator;
nephroprotective agent;
plant metabolite;
radical scavenger;
vascular endothelial growth factor receptor antagonist
diosmetin
[no description available]		2.41103'-hydroxyflavonoid;
monomethoxyflavone;
trihydroxyflavone		angiogenesis inhibitor;
anti-inflammatory agent;
antineoplastic agent;
antioxidant;
apoptosis inducer;
bone density conservation agent;
cardioprotective agent;
plant metabolite;
tropomyosin-related kinase B receptor agonist;
vasodilator agent
genkwanin
genkwanin: structure. genkwanin : A monomethoxyflavone that is apigenin in which the hydroxy group at position 7 is methylated.		3.3160dihydroxyflavone;
monomethoxyflavone		metabolite
nitrophenols
Nitrophenols: PHENOLS carrying nitro group substituents.		2.1310
yuanhuacin
[no description available]		2.5420
thromboplastin
Thromboplastin: Constituent composed of protein and phospholipid that is widely distributed in many tissues. It serves as a cofactor with factor VIIa to activate factor X in the extrinsic pathway of blood coagulation.		2.0510
ConditionIndicatedRelationship StrengthStudiesTrials
Malignant Melanoma
[description not available]		02.1710
Melanoma
A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)		02.1710
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.3110
Bone Cancer
[description not available]		02.4110
Osteogenic Sarcoma
[description not available]		02.4110
Bone Neoplasms
Tumors or cancer located in bone tissue or specific BONES.		02.4110
Osteosarcoma
A sarcoma originating in bone-forming cells, affecting the ends of long bones. It is the most common and most malignant of sarcomas of the bones, and occurs chiefly among 10- to 25-year-old youths. (From Stedman, 25th ed)		07.4110
Benign Neoplasms
[description not available]		02.4110
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.4110
Hepatocellular Carcinoma
[description not available]		07.2110
Cancer of Liver
[description not available]		02.2110
Carcinoma, Hepatocellular
A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.		02.2110
Liver Neoplasms
Tumors or cancer of the LIVER.		02.2110
Carcinoma, Non-Small Cell Lung
[description not available]		02.2510
Cancer of Lung
[description not available]		02.2510
Carcinoma, Non-Small-Cell Lung
A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.		02.2510
Lung Neoplasms
Tumors or cancer of the LUNG.		02.2510
Glial Cell Tumors
[description not available]		02.0810
Glioma
Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)		07.0810