Compounds > convicine
Page last updated: 2024-12-07

convicine

Description

Convicine is a naturally occurring pyrimidine glycoside found in fava beans (Vicia faba). It is a potent inhibitor of the enzyme glucose-6-phosphate dehydrogenase (G6PD), which is responsible for the first step in the pentose phosphate pathway. This pathway is important for the production of NADPH, a reducing agent that protects cells from oxidative damage. Individuals with G6PD deficiency are unable to efficiently produce NADPH and are therefore susceptible to hemolytic anemia upon exposure to oxidative stressors, such as fava beans. Convicine is thought to be responsible for favism, a condition characterized by hemolytic anemia, jaundice, and other symptoms that can occur in individuals with G6PD deficiency who consume fava beans. Convicine has also been shown to exhibit antitumor activity in vitro. Its synthesis involves the condensation of cytosine and D-glucose. The study of convicine is important for understanding the pathogenesis of favism and for exploring its potential therapeutic applications.'

convicine: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID88000
CHEBI ID3867
SCHEMBL ID4630048
MeSH IDM0050095

Synonyms (21)

Synonym
convicine
C08430
19286-37-4
6-amino-5-(b-d-glucopyranosyloxy)-2,4(1h,3h)-pyrimidinedione
AC1L3ETZ ,
6-amino-5-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1h-pyrimidine-2,4-dione
AC1Q6LTN ,
unii-6o6r2591x5
6o6r2591x5 ,
convicine [mi]
SCHEMBL4630048
CHEBI:3867
6-amino-5-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-1h-pyrimidine-2,4-dione
surecn4630048
6-amino-2-hydroxy-5-(beta-d-glucopyranosyloxy)-4-pyrimidinone
DTXSID60940958
4-amino-2,6-dihydroxypyrimidin-5-yl hexopyranoside
Q27106221
CS-0113903
HY-135738
6-amino-5-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)pyrimidine-2,4(1h,3h)-dione

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"This study in the rat established the effects that a broad-spectrum and poorly absorbed antibiotic, neomycin sulfate, had on the in vitro and in vivo hydrolysis of vicine and convicine by the intestinal microflora, and on vicine- and convicine-induced depletion of blood glutathione and the resulting toxicity."( Effect of neomycin on the hydrolysis and toxicity of vicine and convicine in rats.
Arbid, MS; Frohlich, AA; Madhyastha, MS; Marquardt, RR, 1993)		0.72
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
glycosideA 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]

Research

Studies (22)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (31.82)18.7374
1990's6 (27.27)18.2507
2000's1 (4.55)29.6817
2010's6 (27.27)24.3611
2020's2 (9.09)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 33.01

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

MetricThis Compound (vs All)
Research Demand Index33.01 (24.57)
Research Supply Index3.22 (2.92)
Research Growth Index5.39 (4.65)
Search Engine Demand Index41.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (33.01)

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%
Other24 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
uracil
2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder		3.3470pyrimidine nucleobase;
pyrimidone		allergen;
Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
prodrug;
Saccharomyces cerevisiae metabolite
uridine
[no description available]		4.44220uridinesdrug metabolite;
fundamental metabolite;
human metabolite
levodopa
Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease		2.6630amino acid zwitterion;
dopa;
L-tyrosine derivative;
non-proteinogenic L-alpha-amino acid		allelochemical;
antidyskinesia agent;
antiparkinson drug;
dopaminergic agent;
hapten;
human metabolite;
mouse metabolite;
neurotoxin;
plant growth retardant;
plant metabolite;
prodrug
framycetin
Framycetin: A component of NEOMYCIN that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). framycetin : A tetracyclic antibacterial agent derived from neomycin, being a glycoside ester of neamine and neobiosamine B.		1.9810aminoglycosideallergen;
antibacterial drug;
Escherichia coli metabolite
glucose, (beta-d)-isomer
beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.		4.44220D-glucopyranoseepitope;
mouse metabolite
1,7-phenanthroline
[no description available]		1.9610phenanthroline
isouramil
isouramil: aglycone of convicine		7.9140
glycosides
[no description available]		2.6530
tannins
Tannins: Polyphenolic compounds with molecular weights of around 500-3000 daltons and containing enough hydroxyl groups (1-2 per 100 MW) for effective cross linking of other compounds (ASTRINGENTS). The two main types are HYDROLYZABLE TANNINS and CONDENSED TANNINS. Historically, the term has applied to many compounds and plant extracts able to render skin COLLAGEN impervious to degradation. The word tannin derives from the Celtic word for OAK TREE which was used for leather processing.		2.1510
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.		2.3620ascorbic acid;
vitamin C		coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent
vicine
vicine: pyrimidine glycoside found in fava bean; structure		4.44220glycoside
divicine
divicine: RN given refers to parent cpd		8.0950
pyrimidinones
Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.		4.44220
ConditionIndicatedRelationship StrengthStudiesTrials
Favism
Hemolytic anemia due to the ingestion of fava beans or after inhalation of pollen from the Vicia fava plant by persons with glucose-6-phosphate dehydrogenase deficient erythrocytes.		08.69100
Extravascular Hemolysis
[description not available]		02.4120
Hemolysis
The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.		02.4120
Deficiency of Glucose-6-Phosphate Dehydrogenase
[description not available]		02.3720
Glucosephosphate Dehydrogenase Deficiency
A disease-producing enzyme deficiency subject to many variants, some of which cause a deficiency of GLUCOSE-6-PHOSPHATE DEHYDROGENASE activity in erythrocytes, leading to hemolytic anemia.		02.3720
Plasmodium falciparum Malaria
[description not available]		01.9910
Malaria, Falciparum
Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.		01.9910
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