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

dictyostatin

Description

dictyostatin: a macrocyclic compound; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID11353099
CHEMBL ID226880
SCHEMBL ID14094924
MeSH IDM0445373

Synonyms (7)

Synonym
CHEMBL226880
dictyostatin
SCHEMBL14094924
(3z,5e,7r,8s,10s,11z,13s,14r,15s,17s,20r,21s,22s)-22-[(2s,3z)-hexa-3,5-dien-2-yl]-8,10,14,20-tetrahydroxy-7,13,15,17,21-pentamethyl-1-oxacyclodocosa-3,5,11-trien-2-one
(3~{z},5~{e},7~{r},8~{s},10~{s},11~{z},13~{s},14~{r},15~{s},17~{s},20~{r},21~{s},22~{s})-22-[(2~{s},3~{z})-hexa-3,5-dien-2-yl]-7,13,15,17,21-pentamethyl-8,10,14,20-tetrakis(oxidanyl)-1-oxacyclodocosa-3,5,11-trien-2-one
(-)-dictyostatin
Q43297542

Research Excerpts

Overview

Dictyostatin (DCT, 1) is a complex, flexible polyketide macrolide that demonstrates potent microtubule-polymerization activity. It causes cells to accumulate in the G2/M phase of the cell cycle.

ExcerptReferenceRelevance
"The dictyostatins are a promising class of potential anti-cancer drugs because they are powerful microtubule-stabilizing agents, but the complexity of their chemical structures is a severe impediment to their further development. "( Streamlined syntheses of (-)-dictyostatin, 16-desmethyl-25,26-dihydrodictyostatin, and 6-epi-16-desmethyl-25,26-dihydrodictyostatin.
Balachandran, R; Camarco, DP; Curran, DP; Day, BW; Jiménez, M; Jung, WH; Vogt, A; Zhu, W, 2010)		1.21
"Dictyostatin (DCT, 1) is a complex, flexible polyketide macrolide that demonstrates potent microtubule-polymerization activity. "( Dictyostatin flexibility bridges conformations in solution and in the β-tubulin taxane binding site.
Alcaraz, AA; Curran, DP; Damodaran, K; Jogalekar, AS; Jung, WH; Kriel, FH; Snyder, JP; Zhong, S, 2011)		3.25
"(-)-Dictyostatin is a sponge-derived, 22-member macrolactone natural product shown to cause cells to accumulate in the G2/M phase of the cell cycle, with changes in intracellular microtubules analogous to those observed with paclitaxel treatment. "( Tubulin assembly, taxoid site binding, and cellular effects of the microtubule-stabilizing agent dictyostatin.
Balachandran, R; Brückner, AM; Curran, DP; Day, BW; Edler, MC; Fournier, JH; Fukui, Y; Giuliano, KA; Hamel, E; Madiraju, C; Raccor, BS; Shin, Y; Vogt, A; Zhu, G, 2005)		1.1
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (36)

Assay IDTitleYearJournalArticle
AID294923Cytotoxicity against human PANC1 cells after 72 hrs by MTT assay2007Bioorganic & medicinal chemistry letters, May-01, Volume: 17, Issue:9
Synthesis and biological evaluation of novel analogues of dictyostatin.
AID772395Stabilization of microtubule in HEK293 cells assessed as increase in acetylated alpha-tubulin after 4 hrs by ELISA2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID417071Growth inhibition of human AsPC1 cells after 72 hrs by MTT assay2009Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6
Total synthesis and biological evaluation of novel C2-C6 region analogues of dictyostatin.
AID772392Fraction unbound in CD1 mouse plasma at 5 mg/kg, ip dministered as single dose2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID417074Growth inhibition of paclitaxel-resistant human NCI/ADR cells after 72 hrs by MTT assay2009Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6
Total synthesis and biological evaluation of novel C2-C6 region analogues of dictyostatin.
AID772384Fraction unbound in CD1 mouse brain at 5 mg/kg, ip administered as single dose2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID294921Cytotoxicity against human AsPC1 cells after 72 hrs by MTT assay2007Bioorganic & medicinal chemistry letters, May-01, Volume: 17, Issue:9
Synthesis and biological evaluation of novel analogues of dictyostatin.
AID772391Plasma concentration in CD1 mouse at 5 mg/kg, ip administered as single dose at 4 hrs2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID410180Cytotoxicity against taxol-resistant human NCI/ADR-RES cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry letters, Dec-01, Volume: 18, Issue:23
Total synthesis and biological evaluation of potent analogues of dictyostatin: modification of the C2-C6 dienoate region.
AID772393Stabilization of microtubule in HEK293 cells assessed as increase in acetylated alpha-tubulin at 1to 10 nM after 4 hrs by ELISA2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID294924Cytotoxicity against human Taxol-adriamycin-resistant NCI cells after 72 hrs by MTT assay2007Bioorganic & medicinal chemistry letters, May-01, Volume: 17, Issue:9
Synthesis and biological evaluation of novel analogues of dictyostatin.
AID410177Cytotoxicity against taxol-sensitive human AsPC1 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry letters, Dec-01, Volume: 18, Issue:23
Total synthesis and biological evaluation of potent analogues of dictyostatin: modification of the C2-C6 dienoate region.
AID291081Displacement of [3H]paclitaxel from bovine brain tubulin at 4 uM2007Journal of medicinal chemistry, Jun-28, Volume: 50, Issue:13
Total synthesis and biological evaluation of C16 analogs of (-)-dictyostatin.
AID410178Cytotoxicity against taxol-sensitive human DLD1 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry letters, Dec-01, Volume: 18, Issue:23
Total synthesis and biological evaluation of potent analogues of dictyostatin: modification of the C2-C6 dienoate region.
AID417076Cell cycle arrest in human PANC1 cells assessed as accumulation at S phase at 100 nM after 24 hrs by flow cytometry2009Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6
Total synthesis and biological evaluation of novel C2-C6 region analogues of dictyostatin.
AID318809Cytotoxicity against human PANC1 cells after 72 hrs by MTT assay2008Journal of natural products, Mar, Volume: 71, Issue:3
Synthesis and biological evaluation of 10,11-dihydrodictyostatin, a potent analogue of the marine anticancer agent dictyostatin.
AID318807Cytotoxicity against human AsPC1 cells after 72 hrs by MTT assay2008Journal of natural products, Mar, Volume: 71, Issue:3
Synthesis and biological evaluation of 10,11-dihydrodictyostatin, a potent analogue of the marine anticancer agent dictyostatin.
AID291078Growth inhibition of beta tubulin Phe270Val mutant expressing human 1A9/Ptx10 cells after 72 hrs2007Journal of medicinal chemistry, Jun-28, Volume: 50, Issue:13
Total synthesis and biological evaluation of C16 analogs of (-)-dictyostatin.
AID772386Drug uptake in CD1 mouse brain at 5 mg/kg, ip administered as single dose at 4 hrs2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID291076Increase in cellular tubulin polymer mass in HeLa cells assessed as minimum detectable effective concentration after 21 hrs2007Journal of medicinal chemistry, Jun-28, Volume: 50, Issue:13
Total synthesis and biological evaluation of C16 analogs of (-)-dictyostatin.
AID291079Growth inhibition of beta tubulin A364T mutant expressing human 1A9/Ptx22 cells after 72 hrs2007Journal of medicinal chemistry, Jun-28, Volume: 50, Issue:13
Total synthesis and biological evaluation of C16 analogs of (-)-dictyostatin.
AID291080Inhibition of bovine brain tubulin polymerization at 10 uM relative to paclitaxel2007Journal of medicinal chemistry, Jun-28, Volume: 50, Issue:13
Total synthesis and biological evaluation of C16 analogs of (-)-dictyostatin.
AID772383Stabilization of microtubule brain in CD1 mouse assessed as increase in acetylated alpha-tubulin at 5 mg/kg, ip administered as single dose measured after 7 days relative to vehicle-treated control2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID291077Growth inhibition of human 1A9 cells after 72 hrs2007Journal of medicinal chemistry, Jun-28, Volume: 50, Issue:13
Total synthesis and biological evaluation of C16 analogs of (-)-dictyostatin.
AID410179Cytotoxicity against taxol-sensitive human PANC1 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry letters, Dec-01, Volume: 18, Issue:23
Total synthesis and biological evaluation of potent analogues of dictyostatin: modification of the C2-C6 dienoate region.
AID772388Plasma concentration in CD1 mouse at 5 mg/kg, ip administered as single dose at 16 hrs2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID318808Cytotoxicity against human DLD1 cells after 72 hrs by MTT assay2008Journal of natural products, Mar, Volume: 71, Issue:3
Synthesis and biological evaluation of 10,11-dihydrodictyostatin, a potent analogue of the marine anticancer agent dictyostatin.
AID417075Cell cycle arrest in human PANC1 cells assessed as accumulation at G1 phase at 100 nM after 24 hrs by flow cytometry2009Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6
Total synthesis and biological evaluation of novel C2-C6 region analogues of dictyostatin.
AID318810Cytotoxicity against taxol-resistant human NCI/ADR cells after 72 hrs by MTT assay2008Journal of natural products, Mar, Volume: 71, Issue:3
Synthesis and biological evaluation of 10,11-dihydrodictyostatin, a potent analogue of the marine anticancer agent dictyostatin.
AID772387Drug uptake in CD1 mouse brain at 5 mg/kg, ip administered as single dose at 16 hrs2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID294922Cytotoxicity against human DLD1 cells after 72 hrs by MTT assay2007Bioorganic & medicinal chemistry letters, May-01, Volume: 17, Issue:9
Synthesis and biological evaluation of novel analogues of dictyostatin.
AID772390AUC (0.25 to 4 hrs) in CD1 mouse plasma at 5 mg/kg, ip administered as single dose at 4 hrs2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID417073Growth inhibition of human PANC1 cells after 72 hrs by MTT assay2009Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6
Total synthesis and biological evaluation of novel C2-C6 region analogues of dictyostatin.
AID772385AUC (0.5 to 16 hrs) in CD1 mouse brain at 5 mg/kg, ip administered as single dose at 4 hrs2013ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9
MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications.
AID417072Growth inhibition of human DLD1 cells after 72 hrs by MTT assay2009Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6
Total synthesis and biological evaluation of novel C2-C6 region analogues of dictyostatin.
AID417077Cell cycle arrest in human PANC1 cells assessed as accumulation at G2/M phase at 100 nM after 24 hrs by flow cytometry2009Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6
Total synthesis and biological evaluation of novel C2-C6 region analogues of dictyostatin.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (41)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's31 (75.61)29.6817
2010's10 (24.39)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 18.19

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 Index18.19 (24.57)
Research Supply Index3.74 (2.92)
Research Growth Index4.29 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (18.19)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews5 (12.20%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other36 (87.80%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
carbamates
[no description available]		6.24140amino-acid anion
1-anilino-8-naphthalenesulfonate
1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.		2.0310aminonaphthalene;
naphthalenesulfonic acid		fluorescent probe
guanidine
Guanidine: A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.. guanidine : An aminocarboxamidine, the parent compound of the guanidines.		3.1310carboxamidine;
guanidines;
one-carbon compound
phenylalanine
Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.		2.0210amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
phenylalanine;
proteinogenic amino acid		algal metabolite;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
Escherichia coli metabolite;
human xenobiotic metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
valine
Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.		2.0210L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid;
valine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
propane
Propane: A three carbon alkane with the formula H3CCH2CH3.		2.0410alkane;
gas molecular entity		food propellant
erythromycin
Erythromycin: A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.. erythromycin : Any of several wide-spectrum macrolide antibiotics obtained from actinomycete Saccharopolyspora erythraea (formerly known as Streptomyces erythraeus).. erythromycin A : An erythromycin that consists of erythronolide A having 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively.		3.1110cyclic ketone;
erythromycin
fluorescein-5-isothiocyanate
Fluorescein-5-isothiocyanate: Fluorescent probe capable of being conjugated to tissue and proteins. It is used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.. fluorescein 5-isothiocyanate : The 5-isomer of fluorescein isothiocyanate. Acts as a fluorescent probe capable of being conjugated to tissue and proteins; used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.		2.0410fluorescein isothiocyanate
fluorine
Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.		2.0310diatomic fluorine;
gas molecular entity		NMR chemical shift reference compound
iodine
[no description available]		2.0810halide anion;
monoatomic iodine		human metabolite
paclitaxel
Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).		3.91120taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
desoxyepothilone b
desoxyepothilone B: microtubule-targeted antitumor agent; lacking the epoxide of epothilone B; may be equiv to epothilone D. epothilone D : An epithilone that is epithilone C in which the hydrogen at position 13 of the oxacyclohexadec-13-ene-2,6-dione macrocycle has been replaced by a methyl group.		2.0810epothilonemicrotubule-stabilising agent
epothilone b
[no description available]		7.4620epothilone;
epoxide		antineoplastic agent;
apoptosis inducer;
microtubule-stabilising agent
epothilone a
Epothilones: A group of 16-member MACROLIDES which stabilize MICROTUBULES in a manner similar to PACLITAXEL. They were originally found in the myxobacterium Sorangium cellulosum, now renamed to Polyangium (MYXOCOCCALES).		3.8330epothilone;
epoxide		antineoplastic agent;
metabolite;
microtubule-stabilising agent;
tubulin modulator
discodermolide
[no description available]		3.1450diterpenoid
lithium
Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.		2.0510alkali metal atom
tetrodotoxin
Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.. tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.		3.1310azatetracycloalkane;
oxatetracycloalkane;
quinazoline alkaloid		animal metabolite;
bacterial metabolite;
marine metabolite;
neurotoxin;
voltage-gated sodium channel blocker
tautomycetin
tautomycetin: isolated from Streptomyces griseochromogenes		3.1110sesquiterpenoid
amphidinolide a
amphidinolide A: structure in first source		4.0420
batzelladine a
batzelladine A: strucutre in first source. batzelladine A : A carboxylic ester obtained by the formal condensation of (2aS,3S,4R,7R,8aS)-4-methyl-7-nonyl-2,2a,3,4,6,7,8,8a-octahydro-1H-5,6,8b-triazaacenaphthylene-3-carboxylic acid with the hydroxy group of 4-carbamimidamidobutyl (3R)-3-(9-hydroxynonyl)-1-imino-1,2,3,5,6,7-hexahydropyrrolo[1,2-c]pyrimidine-4-carboxylate. Isolated from a bright red Caribbean sponge, Batzella, it has potential anti-HIV activity.		4.0420alkaloid;
carboxylic ester;
guanidines;
organic heterotricyclic compound;
pyrrolopyrimidine;
triazaacenaphthylene		anti-HIV-1 agent;
metabolite
discodermolide
discodermolide: a lactone-bearing polyhydroxylated alkatetraene from the marine sponge Discodermia dissoluta; microtubule-stabilizing agent like taxol		6.24140
hoe 33342
bisbenzimide ethoxide trihydrochloride: benzimidazole fluorescent dye		2.0410
azaspiracid
azaspiracid: a toxin from mussels produced in Ireland that caused multiple organ damage; structure in first source		3.1310
crambescidin 800
crambescidin 800: structure in first source. crambescidin 800 : An organic heteropentacyclic guanidine alkaloid isolated from the marine sponge Crambe crambe and Batzella. It exhibits anti-HIV-1 and anti-HSV-1 activity.		3.1310alkaloid;
carboxylic ester;
guanidines;
monocarboxylic acid amide;
organic heteropentacyclic compound;
primary amino compound;
secondary alcohol;
spiro compound		anti-HIV-1 agent;
anti-HSV-1 agent;
antimalarial;
marine metabolite
amphidinolide e
amphidinolide E: cytotoxic macrolide from Amphidinium sp.; structure in first source		2.0410
ConditionIndicatedRelationship StrengthStudiesTrials
Disease Exacerbation
[description not available]		02.0410
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		02.0410
Breast Cancer
[description not available]		07.4320
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.4320
Benign Neoplasms
[description not available]		02.0610
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.		02.0610
Cancer of Ovary
[description not available]		02.4320
Ovarian Neoplasms
Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.		02.4320
Carcinoma, Anaplastic
[description not available]		02.0410
Carcinoma
A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.		02.0410
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