Page last updated: 2024-11-08

flavin-adenine dinucleotide

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

Description

Flavin-Adenine Dinucleotide: A condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID643975
CHEMBL ID1232653
CHEBI ID16238
SCHEMBL ID505095
MeSH IDM0008169

Synonyms (63)

Synonym
einecs 205-663-1
nsc 112207
flavin adenin dinucleotide
CHEMBL1232653
CHEBI:16238 ,
adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with riboflavine
adenosine 5'-(3-{d-ribo-5-[7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2h)-yl]-2,3,4-trihydroxypentyl} dihydrogen diphosphate)
adenosine 5'-[3-(riboflavin-5'-yl) dihydrogen diphosphate]
riboflavin 5'-(trihydrogen diphosphate), 5'-5'-ester with adenosine
flavin adenine dinucleotide (jan)
D00005
adeflavin (tn)
flavin-adenine dinucleotide
riboflavin 5'-adenosine diphosphate
isoalloxazine-adenine dinucleotide
adenine-flavine dinucleotide
riboflavine-adenine dinucleotide
adenine-flavin dinucleotide
flavine-adenine dinucleotide
146-14-5
flavin adenine dinucleotide
adenine-riboflavin dinucleotide
adenine-riboflavine dinucleotide
flavine adenosine diphosphate
riboflavin-adenine dinucleotide
nsc-112207
fademin
riboflavin 5'-(trihydrogen diphosphate), p'-5'-ester with adenosine
flamitajin
adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with riboflavine (8ci)
riboflavine, 5'-ester with adenosine 5'-diphosphate (8ci)
C00016
DB03147
flavine adenine dinucleotide
gtpl5184
[({[(2r,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2r,3s,4s)-5-{7,8-dimethyl-2,4-dioxo-2h,3h,4h,10h-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy})phosphinic acid
[[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2r,3s,4s)-5-(7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] hydrogen phosphate
4-26-00-03632 (beilstein handbook reference)
unii-zc44yti8kk
zc44yti8kk ,
riboflavin 5'-(trihydrogen diphosphate), p'->5'-ester with adenosine
riboflavin 5'-(trihydrogen diphosphate), p'.fwdarw.5'-ester with adenosine
flavine adenine dinucleotide [who-dd]
flavin-adenine dinucleotide [mi]
riboflavine 5'-(trihydrogen diphosphate) 5'->5'-ester with adenosine
AKOS015915279
DTXSID4048307
SCHEMBL505095
{[(2r,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2r,3s,4s)-5-{7,8-dimethyl-2,4-dioxo-2h,3h,4h,10h-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid
flavinadenindinucleotid
1h-purin-6-amine flavin dinucleotide
flaziren
1h-purin-6-amine flavine dinucleotide
[(2r,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2r,3s,4s)-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2h)-yl)-2,3,4-trihydroxypentyl dihydrogen diphosphate (non-preferred name)
3-hydroxy-1h-indole-2-carboxylicacidethylester
(((2r,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-3,4-dihydroxyoxolan-2-yl)methoxy)(((((2r,3s,4s)-5-(7,8-dimethyl-2,4-dioxo-2h,3h,4h,10h-benzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl)oxy)(hydroxy)phosphoryl)oxy)phosphinic acid
VWWQXMAJTJZDQX-UYBVJOGSSA-N
Q28746
flavin-adenine-dinucleotide
flavinadeninedinucleotide,riboflavinsquare5'-adenosinesquarediphosphate,adenineflavindinucleotide,isoalloxazinesquareadeninedinucleotide,fad
flavinadeninedinucleotide
EN300-19733360
F87829

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"A major concern of contemporary medicine is the adverse effects resulting from the use of prescribed and over-the-counter pharmacologic agents."( Nutritional parameters that alter hepatic drug metabolism, conjugation, and toxicity.
Bidlack, WR; Brown, RC; Mohan, C, 1986
)
0.27
" A phenomenological double logistic model was proposed to quantify and relate the observed kinetic changes of fluorescence to the toxic potency of chemical compounds."( Non-invasive monitoring of cytotoxicity based on kinetic changes of cellular autofluorescence.
Bednarkiewicz, A; Rodrigues, RM; Whelan, MP, 2011
)
0.37

Compound-Compound Interactions

ExcerptReferenceRelevance
"This paper describes a new method, multiphoton excitation fluorescence detection combined with capillary electrophoresis separation."( [Study on multi-photon excited fluorescence combined with capillary electrophoresis].
Ma, WY; Sun, YX; Zhu, F, 2005
)
0.33

Bioavailability

ExcerptReferenceRelevance
" Ethanol markedly diminished the bioavailability of [14C]FAD to a greater degree than that of [14C]riboflavin."( Mechanisms underlying the differential effects of ethanol on the bioavailability of riboflavin and flavin adenine dinucleotide.
Huang, YP; Pinto, J; Rivlin, RS, 1987
)
0.27

Dosage Studied

ExcerptRelevanceReference
" Riboflavin was given without effect even at a high dosage level."( Deficient cytochrome b5 reductase activity in nontoxic goiter with iodide organification defect.
Kusakabe, T, 1975
)
0.25
" This dosage regimen of riboflavin did not change the activity of DMN demethylase I in the normal animals."( Effects of riboflavin on the dimethylnitrosamine demethylase system in the rat liver.
Ruchirawat, M; Saengchan, S, 1984
)
0.27
" The affinity of FMN, FAD and the precursor riboflavin (RF) to an unsaturated phospholipid bilayer model as well as the location of the probes within the lipid bilayer were assessed from united-atom molecular dynamics simulations carried out on an unsaturated phospholipid bilayer model system, and the theoretical and experimental characterization of the two probes within biomembranes was complemented with the light microscopy survey of the cell morphology of L929 fibroblast cells cultivated in the presence of various dosage of FAD/FMN."( Spectroscopic, molecular dynamics simulation and biological studies of Flavin MonoNucleotide and Flavin Adenine Dinucleotide in biomimetic systems.
Angelescu, DG; Craciunescu, O; Moldovan, L; Tatia, R; Voicescu, M, 2021
)
0.62
" Dose-response competition binding experiments using lysates of human or bacterial cells followed by quantitative mass spectrometry recapitulated targets of 9 molecules with <100 μM affinity."( Merits of Diazirine Photo-Immobilization for Target Profiling of Natural Products and Cofactors.
Abele, M; Höfer, S; Hornisch, M; Kuster, B; Médard, G; Prokofeva, P, 2022
)
0.72
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (5)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Escherichia coli metaboliteAny bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
prosthetic groupA tightly bound, specific nonpolypeptide unit in a protein determining and involved in its biological activity.
cofactorAn organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
[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 (2)

ClassDescription
flavin adenine dinucleotide
vitamin B2Any member of a group of vitamers that belong to the chemical structural class called flavins that exhibit biological activity against vitamin B2 deficiency. Symptoms associated with vitamin B2 deficiency include glossitis, seborrhea, angular stomaitis, cheilosis and photophobia. The vitamers include riboflavin and its phosphate derivatives (and includes their salt, ionised and hydrate forms).
[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]

Pathways (45)

PathwayProteinsCompounds
eNOS activation and regulation1326
Histidine, lysine, phenylalanine, tyrosine, proline and tryptophan catabolism4485
Phenylalanine and tyrosine catabolism1131
Citric Acid Cycle2127
Riboflavin Metabolism515
Congenital Lactic Acidosis2127
Fumarase Deficiency2127
Mitochondrial Complex II Deficiency2127
2-Ketoglutarate Dehydrogenase Complex Deficiency2127
Pyruvate Dehydrogenase Deficiency (E3)2127
Pyruvate Dehydrogenase Deficiency (E2)2127
Warburg Effect4652
Flavin Biosynthesis1024
The Oncogenic Action of 2-Hydroxyglutarate2734
The Oncogenic Action of Succinate2933
The Oncogenic Action of Fumarate2934
Glutaminolysis and Cancer3536
The Oncogenic Action of L-2-Hydroxyglutarate in Hydroxyglutaric aciduria2835
The Oncogenic Action of D-2-Hydroxyglutarate in Hydroxyglutaric aciduria2936
Cytokinins Degradation113
Latent infection of Homo sapiens with Mycobacterium tuberculosis3232
LPS and Citrate Signaling and Inflammation2311
Nsp9 interactions (COVID-19 Disease Map)8330
Mitochondrial complex II assembly01
Riboflavin and CoQ disorders1627
Glyoxylate metabolism1115
Diet-dependent trimethylamine/trimethylamine N-oxide metabolism112
Metabolic Epileptic Disorders2589
Cytosolic iron-sulfur cluster assembly (yeast)129
valine degradation I018
isoleucine degradation I018
Electron transport chain010
TCA cycle (Krebs cycle)3019
Neurotransmitter clearance in synaptic cleft022
Neurotransmitter release cycle021
Catalytic cycle of mammalian FMOs07
Electron transport chain: OXPHOS system in mitochondria010
Selenium micronutrient network095
Vitamin B12 metabolism050
Folate metabolism156
Dopamine metabolism032
Methionine de novo and salvage pathway148
Vitamin B12 disorders1313
Cerebral organic acidurias, including diseases527
Catalytic cycle of mammalian flavin-containing monooxygenases (FMOs)08

Bioassays (8)

Assay IDTitleYearJournalArticle
AID554815Drug activation in metronidazole-susceptible Helicobacter pylori RIG 117 J0 lysate2009Antimicrobial agents and chemotherapy, May, Volume: 53, Issue:5
A redox basis for metronidazole resistance in Helicobacter pylori.
AID554817Drug activation in metronidazole-susceptible Helicobacter pylori HER 126 V1 lysate2009Antimicrobial agents and chemotherapy, May, Volume: 53, Issue:5
A redox basis for metronidazole resistance in Helicobacter pylori.
AID554814Drug activation in metronidazole-susceptible Helicobacter pylori 10593/2 lysate2009Antimicrobial agents and chemotherapy, May, Volume: 53, Issue:5
A redox basis for metronidazole resistance in Helicobacter pylori.
AID554820Drug activation in metronidazole-resistant Helicobacter pylori CAS 015 J56 lysate harboring rdxA L132stop and frxA L39stop mutant genes2009Antimicrobial agents and chemotherapy, May, Volume: 53, Issue:5
A redox basis for metronidazole resistance in Helicobacter pylori.
AID554816Drug activation in metronidazole-susceptible Helicobacter pylori CAS 015 J0 lysate2009Antimicrobial agents and chemotherapy, May, Volume: 53, Issue:5
A redox basis for metronidazole resistance in Helicobacter pylori.
AID554821Drug activation in metronidazole-resistant Helicobacter pylori HER 126 V4 lysate2009Antimicrobial agents and chemotherapy, May, Volume: 53, Issue:5
A redox basis for metronidazole resistance in Helicobacter pylori.
AID554819Drug activation in metronidazole-resistant Helicobacter pylori RIG 117 J56 lysate2009Antimicrobial agents and chemotherapy, May, Volume: 53, Issue:5
A redox basis for metronidazole resistance in Helicobacter pylori.
AID554818Drug activation in metronidazole-resistant Helicobacter pylori 10593a/2 lysate2009Antimicrobial agents and chemotherapy, May, Volume: 53, Issue:5
A redox basis for metronidazole resistance in Helicobacter pylori.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (4,660)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901740 (37.34)18.7374
1990's733 (15.73)18.2507
2000's965 (20.71)29.6817
2010's891 (19.12)24.3611
2020's331 (7.10)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 93.86

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index93.86 (24.57)
Research Supply Index8.48 (2.92)
Research Growth Index4.52 (4.65)
Search Engine Demand Index174.21 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (93.86)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials14 (0.29%)5.53%
Reviews214 (4.46%)6.00%
Case Studies23 (0.48%)4.05%
Observational1 (0.02%)0.25%
Other4,544 (94.75%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]