didymin profile

didymin: a dietary glycoside from citrus fruits that induces Fas-mediated apoptotic pathway in human non-small-cell lung cancer cells in vitro and in vivo; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Flora	Rank	Flora Definition	Family	Family Definition
Citrus	genus	A plant genus of the family RUTACEAE. They bear the familiar citrus fruits including oranges, grapefruit, lemons, and limes. There are many hybrids which makes the nomenclature confusing.[MeSH]	Rutaceae	A plant family in the order Sapindales that grows in warmer regions and has conspicuous flowers.[MeSH]

ID Source	ID
PubMed CID	16760075
CHEBI ID	176179
SCHEMBL ID	497764
MeSH ID	M0550030

Synonym
CHEBI:176179
(2s)-5-hydroxy-2-(4-methoxyphenyl)-7-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
14259-47-3
NCGC00163539-01
didymin
einecs 238-139-6
isosakuranetin-7-o-rutinoside
unii-02q5os3tu3
(s)-7-((6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-methoxyphenyl)-4h-benzopyran-4-one
neoponcirin
02q5os3tu3 ,
isosakuranetin-7-beta-rutinoside
S9235
AKOS016010158
mfcd00151177
SCHEMBL497764
isosakuranetin 7-o-rutinoside
isosakuranetin 7-rutinoside
didymin, analytical standard
sr-05000002279
SR-05000002279-2
4h-1-benzopyran-4-one, 7-((6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-methoxyphenyl)-, (s)-
(s)-7-[[6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-methoxyphenyl)-4h-benzopyran-4-one
(s)-5-hydroxy-2-(4-methoxyphenyl)-7-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-((((2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)methyl)tetrahydro-2h-pyran-2-yl)oxy)chroman-4-one
iso-sakuranetin-7-putinoside
(s)-5-hydroxy-2-(4-methoxyphenyl)-7-((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(((2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yloxy)methyl)tetrahydro-2h-pyran-2-yloxy)chroman-4-one
DTXSID90931536
(2s)-7-((6-o-(6-deoxy-.alpha.-l-mannopyranosyl)-.beta.-d-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-methoxyphenyl)-4h-1-benzopyran-4-one
citrifoliol-7-o-rutinoside
4'-methoxy-5,7-dihydroxyflavanone 7-o-rutinoside
4h-1-benzopyran-4-one, 7-((6-o-(6-deoxy-.alpha.-l-mannopyranosyl)-.beta.-d-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-methoxyphenyl)-, (s)-
flavanone, 5,7-dihydroxy-4'-methoxy-, 7.beta.-rutinoside
didymine
4h-1-benzopyran-4-one, 7-((6-o-(6-deoxy-.alpha.-l-mannopyranosyl)-.beta.-d-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-methoxyphenyl)-, (2s)-
didymin [usp-rs]
Q63399321
CCG-270180
CS-0018573
HY-N2068
A885172
AC-34874
AS-75739
flavanone, 5,7-dihydroxy-4'-methoxy-, 7beta-rutinoside
didymin (usp-rs)
(2s)-7-((6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-methoxyphenyl)-4h-1-benzopyran-4-one
4h-1-benzopyran-4-one, 7-((6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-methoxyphenyl)-, (2s)-
Z3235033284
EX-A8002X

Excerpt	Reference	Relevance
"Didymin is a naturally occurring orally active flavonoid glycoside (isosakuranetin 7-O-rutinoside) found in various citrus fruits, which has been previously reported to possess a wide variety of pharmacological activities including anticancer, antioxidant, antinociceptive, neuroprotective, hepatoprotective, inflammatory, and cardiovascular. "	( Didymin, a dietary citrus flavonoid exhibits anti-diabetic complications and promotes glucose uptake through the activation of PI3K/Akt signaling pathway in insulin-resistant HepG2 cells. Ali, MY; Chang, MS; Iqbal, J; Jannat, S; Park, SK; Rahman, MM; Zaib, S, 2019)	3.4
"Didymin is a citrus-derived natural compound that kills p53 wild-type as well as drug-resistant p53-mutant neuroblastoma cells in culture."	( Didymin: an orally active citrus flavonoid for targeting neuroblastoma. Awasthi, S; Horne, D; Singhal, J; Singhal, P; Singhal, S; Singhal, SS, 2017)	2.62

Excerpt	Reference	Relevance
"Didymin has been reported to have a protective effect on intracerebral hemorrhage."	( Didymin Alleviates Cerebral Ischemia-Reperfusion Injury by Activating the PPAR Signaling Pathway. Li, Q; Liu, X; Zhang, H, 2022)	2.89
"Didymin has been reported to have anti-cancer potential. "	( Didymin Alleviates Hepatic Fibrosis Through Inhibiting ERK and PI3K/Akt Pathways via Regulation of Raf Kinase Inhibitor Protein. Bai, F; Huang, Q; Lin, X; Lu, C; Lu, S; Lu, Z; Nie, J; Wei, J; Zhu, X, 2016)	3.32

Excerpt	Reference	Relevance
"Didymin pretreatment decreased apoptotic rates, reduced levels of Bax and c-caspase-3, and increased Bcl-2 level in vivo and in vitro. "	( Didymin Alleviates Cerebral Ischemia-Reperfusion Injury by Activating the PPAR Signaling Pathway. Li, Q; Liu, X; Zhang, H, 2022)	3.61

Class	Description
flavonoids	Any 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.
glycoside	A glycosyl compound resulting from the attachment of a glycosyl group to a non-acyl group RO-, RS-, RSe-, etc. The bond between the glycosyl group and the non-acyl group is called a glycosidic bond. By extension, the terms N-glycosides and C-glycosides are used as class names for glycosylamines and for compounds having a glycosyl group attached to a hydrocarbyl group respectively. These terms are misnomers and should not be used. The preferred terms are glycosylamines and C-glycosyl compounds, respectively.
[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]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	0 (0.00)	29.6817
2010's	14 (66.67)	24.3611
2020's	7 (33.33)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	3 (14.29%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	18 (85.71%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
citric acid, anhydrous Citric Acid: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.. citric acid : A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.	2.07	1	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	2.63	2	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
hematoxylin Hematoxylin: A dye obtained from the heartwood of logwood (Haematoxylon campechianum Linn., Leguminosae) used as a stain in microscopy and in the manufacture of ink.	2.41	1	organic heterotetracyclic compound; oxacycle; polyphenol; tertiary alcohol	histological dye; plant metabolite
hesperidin Hesperidin: A flavanone glycoside found in CITRUS fruit peels.. hesperidin : A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	3.93	3	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen
eosine yellowish-(ys) Eosine Yellowish-(YS): A versatile red dye used in cosmetics, pharmaceuticals, textiles, etc., and as tissue stain, vital stain, and counterstain with HEMATOXYLIN. It is also used in special culture media.. eosin YS dye : An organic sodium salt that is 2',4',5',7'-tetrabromofluorescein in which the carboxy group and the phenolic hydroxy group have been deprotonated and the resulting charge is neutralised by two sodium ions.	2.41	1	organic sodium salt; organobromine compound	fluorochrome; histological dye
tangeretin tangeretin: structure given in first source; from citrus plants; inhibits invasion of MO4 mouse cells into embryonic chick heart in vitro. tangeretin : A pentamethoxyflavone flavone with methoxy groups at positions 4', 5, 6 , 7 and 8.. pentamethoxyflavone : A methoxyflavone that is flavone substituted by a five methoxy groups.	3.35	1	pentamethoxyflavone	antineoplastic agent; plant metabolite
hesperetin [no description available]	3.35	1	3'-hydroxyflavanones; 4'-methoxyflavanones; monomethoxyflavanone; trihydroxyflavanone	antineoplastic agent; antioxidant; plant metabolite
oxazolidin-2-one Oxazolidinones: Derivatives of oxazolidin-2-one. They represent an important class of synthetic antibiotic agents.. oxazolidin-2-one : An oxazolidinone that is 1,3-oxazolidine with an oxo substituent at position 2.. oxazolidinone : An oxazolidine containing one or more oxo groups.	2.15	1	carbamate ester; oxazolidinone	metabolite
neoeriocitrin neoeriocitrin: protects against autophagy-inhibiting effects of okadaic acid; isolated from Drynariae rhizome; structure in first source. neoeriocitrin : A flavanone glycoside that is eriodictyol substituted by a 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage.	2.07	1	4'-hydroxyflavanones; disaccharide derivative; flavanone glycoside; neohesperidoside; trihydroxyflavanone	plant metabolite
4-benzyl-3-crotonyl-2-oxazolidinone locostatin: an RKIP inhibitor that reduces cell migration	2.15	1
limonin [no description available]	2.07	1	epoxide; furans; hexacyclic triterpenoid; lactone; limonoid; organic heterohexacyclic compound	inhibitor; metabolite; volatile oil component
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	3.63	2	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
naringin [no description available]	3.63	2	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; neohesperidoside	anti-inflammatory agent; antineoplastic agent; metabolite
isonaringin isonaringin: structure in first source. narirutin : A disaccharide derivative that is (S)-naringenin substituted by a 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.48	2	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; rutinoside	anti-inflammatory agent; antioxidant; metabolite
acetyl coenzyme a Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.	2.31	1	acyl-CoA	acyl donor; coenzyme; effector; fundamental metabolite
glycosides [no description available]	8.21	21
xanthohumol xanthohumol: from hop plant, Humulus lupulus. xanthohumol : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and a prenyl group at position 3'. Isolated from Humulus lupulus, it induces apoptosis in human malignant glioblastoma cells.	3.35	1	aromatic ether; chalcones; polyphenol	anti-HIV-1 agent; antineoplastic agent; antiviral agent; apoptosis inducer; EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor; metabolite
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	2.07	1
diosmin [no description available]	2.17	1	dihydroxyflavanone; disaccharide derivative; glycosyloxyflavone; monomethoxyflavone; rutinoside	anti-inflammatory agent; antioxidant
rhoifolin rhoifolin: from many plants. apigenin 7-O-neohesperidoside : An apigenin derivative having an alpha-(1->2)-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety attached to the 7-hydroxy group.	3.35	1	dihydroxyflavone; glycosyloxyflavone; neohesperidoside	metabolite
bergamottin bergamottin: constituent of bergamot oil; structure given in first source	2.07	1	furanocoumarin	metabolite
6',7'-dihydroxybergamottin 6',7'-dihydroxybergamottin: structure given in first source	2.07	1	psoralens
sudachitin sudachitin: antimicrobial from the peels of Citrus sudachi; structure in first source	3.35	1	ether; flavonoids
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	3.46	2
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	2.07	1	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
neohesperidin [no description available]	3.63	2
poncirin poncirin: isolated from the fructus of Poncirus trifoliata; structure in first source	3.63	2

Condition	Relationship Strength	Studies
Brain Hemorrhage, Cerebral [description not available]	2.41	1
Cerebral Hemorrhage Bleeding into one or both CEREBRAL HEMISPHERES including the BASAL GANGLIA and the CEREBRAL CORTEX. It is often associated with HYPERTENSION and CRANIOCEREBRAL TRAUMA.	7.41	1
Innate Inflammatory Response [description not available]	3.95	3
Cirrhosis, Liver [description not available]	3.53	2
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	3.95	3
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	3.53	2
Injury, Ischemia-Reperfusion [description not available]	2.41	1
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	7.41	1
Cardiovascular Stroke [description not available]	4.02	9
Injury, Myocardial Reperfusion [description not available]	4.02	9
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	4.02	9
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	3.17	1
Fatty Liver, Nonalcoholic [description not available]	3.17	1
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	8.17	1
Colitis Gravis [description not available]	2.31	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.31	1
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	2.31	1
Benign Neoplasms [description not available]	4.01	1
Nervous System Disorders [description not available]	4.01	1
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	4.01	1
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.	4.01	1
Nervous System Diseases Diseases of the central and peripheral nervous system. This includes disorders of the brain, spinal cord, cranial nerves, peripheral nerves, nerve roots, autonomic nervous system, neuromuscular junction, and muscle.	4.01	1
Insulin Sensitivity [description not available]	2.21	1
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	2.21	1
Hepatocellular Carcinoma [description not available]	2.15	1
Cancer of Liver [description not available]	2.15	1
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.	2.15	1
Liver Neoplasms Tumors or cancer of the LIVER.	2.15	1
Acute Liver Injury, Drug-Induced [description not available]	2.15	1
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	2.15	1
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	3.42	2
Carcinoma, Non-Small Cell Lung [description not available]	2.05	1
Cancer of Lung [description not available]	2.05	1
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.	2.05	1
Lung Neoplasms Tumors or cancer of the LUNG.	2.05	1

didymin

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Studies (21)

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Research Demand Index: 28.75

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