Compounds > desacetyluvaricin
Page last updated: 2024-11-07

desacetyluvaricin

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

Description

desacetyluvaricin: isolated from Uvaria accuminata; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
UvariagenusA plant genus of the family ANNONACEAE. Members contain uvarigrin, uvarigrandin, chamuvaritin and other acetogenins and benzylisoquinoline alkaloids.[MeSH]AnnonaceaeThe custard-apple plant family of the order Magnoliales, subclass Magnoliidae, class Magnoliopsida. Some members provide large pulpy fruits and commercial timber. Leaves and wood are often fragrant. Leaves are simple, with smooth margins, and alternately arranged in two rows along the stems.[MeSH]

Cross-References

ID SourceID
PubMed CID127149
CHEMBL ID145449
SCHEMBL ID11961385
MeSH IDM0135561

Synonyms (11)

Synonym
98767-45-4
desacetyluvaricin
3-{13-hydroxy-13-[5''-(1-hydroxy-undecyl)-octahydro-[2,2'']bifuranyl-5-yl]-tridecyl}-5-methyl-5h-furan-2-one(desacetyluvaricin)
bdbm50094725
CHEMBL145449 ,
bullanin
(2s)-4-[(13r)-13-hydroxy-13-[(2r,5r)-5-[(2r,5r)-5-[(1s)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2h-furan-5-one
2(5h)-puranone, 3-(13-hydroxy-13-(octahydro-5'-(1-hydroxyundecyl)(2,2'-bifuran)-5-yl)tridecyl)-5-methyl-
SCHEMBL11961385
3-{13-hydroxy-13-[5'-(1-hydroxyundecyl)[2,2'-bioxolan]-5-yl]tridecyl}-5-methylfuran-2(5h)-one
DTXSID10913091
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)IC50 (µMol)0.00030.00020.00220.0051AID144499
Acyl carrier protein, mitochondrialBos taurus (cattle)IC50 (µMol)0.00030.00020.00220.0051AID144499
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (5)

Processvia Protein(s)Taxonomy
mitochondrial electron transport, NADH to ubiquinoneNADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)
transmembrane transportNADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)
mitochondrial electron transport, NADH to ubiquinoneAcyl carrier protein, mitochondrialBos taurus (cattle)
fatty acid biosynthetic processAcyl carrier protein, mitochondrialBos taurus (cattle)
mitochondrial respiratory chain complex I assemblyAcyl carrier protein, mitochondrialBos taurus (cattle)
[2Fe-2S] cluster assemblyAcyl carrier protein, mitochondrialBos taurus (cattle)
transmembrane transportAcyl carrier protein, mitochondrialBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
NADH dehydrogenase (ubiquinone) activityNADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)
FMN bindingNADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)
metal ion bindingNADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)
NAD bindingNADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)
4 iron, 4 sulfur cluster bindingNADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)
fatty acid bindingAcyl carrier protein, mitochondrialBos taurus (cattle)
NADH dehydrogenase (ubiquinone) activityAcyl carrier protein, mitochondrialBos taurus (cattle)
oxidoreductase activityAcyl carrier protein, mitochondrialBos taurus (cattle)
mitochondrial large ribosomal subunit bindingAcyl carrier protein, mitochondrialBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
mitochondrial inner membraneNADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)
respiratory chain complex INADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrialBos taurus (cattle)
mitochondrial matrixAcyl carrier protein, mitochondrialBos taurus (cattle)
mitochondrial membraneAcyl carrier protein, mitochondrialBos taurus (cattle)
respiratory chain complex IAcyl carrier protein, mitochondrialBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (29)

Assay IDTitleYearJournalArticle
AID380849Cytotoxicity against human HT-29 cells1999Journal of natural products, Aug, Volume: 62, Issue:8
Tryptamine derived amides and acetogenins from the seeds of Rollinia mucosa.
AID355179Cytotoxicity against human PC3 cells after 7 days by MTT assay1996Journal of natural products, Nov, Volume: 59, Issue:11
Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.
AID380846Toxicity in Artemia salina1999Journal of natural products, Aug, Volume: 62, Issue:8
Tryptamine derived amides and acetogenins from the seeds of Rollinia mucosa.
AID380848Cytotoxicity against human MCF7 cells1999Journal of natural products, Aug, Volume: 62, Issue:8
Tryptamine derived amides and acetogenins from the seeds of Rollinia mucosa.
AID233953Ratio of IC50 of DB to that of NADH oxidase2000Journal of medicinal chemistry, Dec-14, Volume: 43, Issue:25
Semisynthesis of antitumoral acetogenins: SAR of functionalized alkyl-chain bis-tetrahydrofuranic acetogenins, specific inhibitors of mitochondrial complex I.
AID1082477Nematicidal activity against second juvenile stage (J2) of Bursaphelenchus xylophilus assessed as mortality at >0.33 ug/ml after 2 days by microtiter plate assay method (Beneficial crop Pine)2011Journal of agricultural and food chemistry, Oct-26, Volume: 59, Issue:20
Nematicidal and antifungal activities of annonaceous acetogenins from Annona squamosa against various plant pathogens.
AID656950Antitumor activity against mouse S180 cells allografted in ip dosed Kunming mouse assessed as tumor growth inhibition administered qd 24 hrs post challenge for 10 days2012Bioorganic & medicinal chemistry letters, Apr-15, Volume: 22, Issue:8
Antitumor activity of annonaceous acetogenins in HepS and S180 xenografts bearing mice.
AID656948Antitumor activity against mouse S180 cells allografted in Kunming mouse assessed as tumor growth inhibition at 60 ug/kg, ip qd administered 24 hrs post challenge for 10 days2012Bioorganic & medicinal chemistry letters, Apr-15, Volume: 22, Issue:8
Antitumor activity of annonaceous acetogenins in HepS and S180 xenografts bearing mice.
AID234411Percent of relative potency by NADH oxidase assay2000Journal of medicinal chemistry, Dec-14, Volume: 43, Issue:25
Semisynthesis of antitumoral acetogenins: SAR of functionalized alkyl-chain bis-tetrahydrofuranic acetogenins, specific inhibitors of mitochondrial complex I.
AID656947Antitumor activity against mouse HepS cells allografted in Kunming mouse assessed as tumor growth inhibition at 60 ug/kg, ip qd administered 24 hrs post challenge for 10 days2012Bioorganic & medicinal chemistry letters, Apr-15, Volume: 22, Issue:8
Antitumor activity of annonaceous acetogenins in HepS and S180 xenografts bearing mice.
AID355175Cytotoxicity against human A549 cells after 7 days by MTT assay1996Journal of natural products, Nov, Volume: 59, Issue:11
Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.
AID380852Cytotoxicity against human PaCa2 cells1999Journal of natural products, Aug, Volume: 62, Issue:8
Tryptamine derived amides and acetogenins from the seeds of Rollinia mucosa.
AID402062Inhibition of NADH-ubiquinone oxidoreductase activity of electron transport protein complex 1 in submitochondrial particles of bovine heart1998Journal of natural products, Aug, Volume: 61, Issue:8
10-Oximeguanacone, the first nitrogenated acetogenin derivative found to be a potent inhibitor of mitochondrial complex I.
AID355180Cytotoxicity against human MIAPaCa2 cells after 7 days by MTT assay1996Journal of natural products, Nov, Volume: 59, Issue:11
Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.
AID656946Antitumor activity against mouse S180 cells allografted in Kunming mouse assessed as tumor growth inhibition at 15 ug/kg, ip qd administered 24 hrs post challenge for 10 days2012Bioorganic & medicinal chemistry letters, Apr-15, Volume: 22, Issue:8
Antitumor activity of annonaceous acetogenins in HepS and S180 xenografts bearing mice.
AID380851Cytotoxicity against human PC-3 cells1999Journal of natural products, Aug, Volume: 62, Issue:8
Tryptamine derived amides and acetogenins from the seeds of Rollinia mucosa.
AID355178Cytotoxicity against human A498 cells after 7 days by MTT assay1996Journal of natural products, Nov, Volume: 59, Issue:11
Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.
AID656945Antitumor activity against mouse HepS cells allografted in Kunming mouse assessed as tumor growth inhibition at 15 ug/kg, ip qd administered 24 hrs post challenge for 10 days2012Bioorganic & medicinal chemistry letters, Apr-15, Volume: 22, Issue:8
Antitumor activity of annonaceous acetogenins in HepS and S180 xenografts bearing mice.
AID402061Inhibition of NADH-oxidase activity of electron transport protein complex 1 in submitochondrial particles of bovine heart1998Journal of natural products, Aug, Volume: 61, Issue:8
10-Oximeguanacone, the first nitrogenated acetogenin derivative found to be a potent inhibitor of mitochondrial complex I.
AID355177Cytotoxicity against human HT29 cells after 7 days by MTT assay1996Journal of natural products, Nov, Volume: 59, Issue:11
Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.
AID144499Inhibition of NADH oxidase activity.2000Journal of medicinal chemistry, Dec-14, Volume: 43, Issue:25
Semisynthesis of antitumoral acetogenins: SAR of functionalized alkyl-chain bis-tetrahydrofuranic acetogenins, specific inhibitors of mitochondrial complex I.
AID144480Inhibition of NADH decylubiquinone (DB) oxidoreductase activity.2000Journal of medicinal chemistry, Dec-14, Volume: 43, Issue:25
Semisynthesis of antitumoral acetogenins: SAR of functionalized alkyl-chain bis-tetrahydrofuranic acetogenins, specific inhibitors of mitochondrial complex I.
AID1082478Nematicidal activity against second juvenile stage (J2) of Bursaphelenchus xylophilus assessed as mortality after 2 days by microtiter plate assay method (Beneficial crop Pine)2011Journal of agricultural and food chemistry, Oct-26, Volume: 59, Issue:20
Nematicidal and antifungal activities of annonaceous acetogenins from Annona squamosa against various plant pathogens.
AID656949Antitumor activity against mouse HepS cells allografted in ip dosed Kunming mouse assessed as tumor growth inhibition administered qd 24 hrs post challenge for 10 days2012Bioorganic & medicinal chemistry letters, Apr-15, Volume: 22, Issue:8
Antitumor activity of annonaceous acetogenins in HepS and S180 xenografts bearing mice.
AID355174Toxicity to Artemia salina1996Journal of natural products, Nov, Volume: 59, Issue:11
Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.
AID355176Cytotoxicity against human MCF7 cells after 7 days by MTT assay1996Journal of natural products, Nov, Volume: 59, Issue:11
Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.
AID234417Relative potency of inhibition of NADH oxidase (IC50); 4-dehydroxy-4-hydroxylimonorolliniastatin-1 as standard2000Journal of medicinal chemistry, Dec-14, Volume: 43, Issue:25
Semisynthesis of antitumoral acetogenins: SAR of functionalized alkyl-chain bis-tetrahydrofuranic acetogenins, specific inhibitors of mitochondrial complex I.
AID380850Cytotoxicity against human A298 cells1999Journal of natural products, Aug, Volume: 62, Issue:8
Tryptamine derived amides and acetogenins from the seeds of Rollinia mucosa.
AID380847Cytotoxicity against human A549 cells1999Journal of natural products, Aug, Volume: 62, Issue:8
Tryptamine derived amides and acetogenins from the seeds of Rollinia mucosa.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (50.00)18.2507
2000's1 (12.50)29.6817
2010's3 (37.50)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: 12.02

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

MetricThis Compound (vs All)
Research Demand Index12.02 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.02)

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%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
dithianone
dithianone: structure. dithianon : A naphthodithiin that is 5,10-dioxo-5,10-dihydronaphtho[2,3-b][1,4]dithiin which is substituted by nitrile groups at positions 2 and 3. It is a broad spectrum fungicide used to control scab, downy mildew, rust, and leaf spot in the commercial growing of grapes and other fruit, citrus, coffee, and vegetables.		2.0610dinitrile;
naphthodithiin;
p-quinones		antifungal agrochemical
benomyl
[no description available]		2.0610aromatic amide;
benzimidazole fungicide;
benzimidazoles;
benzimidazolylcarbamate fungicide;
carbamate ester		acaricide;
anthelminthic drug;
antifungal agrochemical;
microtubule-destabilising agent;
tubulin modulator
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).		2.0710taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
flusilazole
flusilazole: structure given in first source. flusilazole : An organosilicon compound that is dimethylsilane in which the hydrogens attached to the silicon are replaced by p-fluorophenyl groups and a hydrogen attached to one of the methyl groups is replaced by a 1H-1,2,4-triazol-1-yl group. It is a broad-sepctrum fungicide used to protect a variety of crops.		2.0610conazole fungicide;
monofluorobenzenes;
organosilicon compound;
triazole fungicide;
triazoles		antifungal agrochemical;
EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor;
environmental contaminant;
xenobiotic
dimethomorph
[no description available]		2.0610mixture;
morpholine fungicide		antifungal agrochemical;
environmental contaminant;
xenobiotic
fludioxonil
fludioxonil: structure in first source. fludioxonil : A member of the class of benzodioxoles that is 2,2-difluoro-1,3-benzodioxole substituted at position 4 by a 3-cyanopyrrol-4-yl group. A fungicide seed treatment for control of a range of diseases including Fusarium, Rhizoctonia and Alternaria.		2.0610benzodioxoles;
nitrile;
organofluorine compound;
pyrroles		androgen antagonist;
antifungal agrochemical;
estrogen receptor agonist
squamocin
squamocin: from seeds of Annona squamosa; a trihydroxy-bis-tetrahydrofuran fatty acid lactone; inhibits E. coli NADH:quinone oxidoreductase (NDH-1); structure given in first source		210polyketide
validamycin a
validamycin A : A member of the class of validamycins that is (1R,2S,3S,4S,6R)-4-amino-6-(hydroxymethyl)cyclohexane-1,2,3-triol in which the hydroxy group at position 1 has been converted to its beta-D-glucoside and in which one of the hydrogens attached to the nitrogen is replaced by a (1R,4R,5R,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl group. It is the major validamycin produced by Streptomyces hygroscopicus.		2.0610antibiotic fungicide;
polyol;
secondary amino compound;
validamycins		antifungal agrochemical;
EC 2.4.1.231 [alpha,alpha-trehalose phosphorylase (configuration-retaining)] inhibitor;
EC 2.4.1.64 (alpha,alpha-trehalose phosphorylase) inhibitor;
EC 3.2.1.28 (alpha,alpha-trehalase) inhibitor
cinnamaldehyde
3-phenylprop-2-enal : A member of the class of cinnamaldehydes that is prop-2-enal in which a hydrogen at position 3 has been replaced by a phenyl group. The configuration of the double bond is not specified; the name "cinnamaldehyde" is widely used to refer to the E (trans) isomer.. (E)-cinnamaldehyde : The E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes.		2.06103-phenylprop-2-enal;
cinnamaldehydes		antifungal agent;
EC 4.3.1.24 (phenylalanine ammonia-lyase) inhibitor;
flavouring agent;
hypoglycemic agent;
plant metabolite;
sensitiser;
vasodilator agent
Nb-Palmitoyltryptamine
[no description available]		210indoles
trilobacin
trilobacin: from the bark of Asimina triloba; structure given in first source. trilobacin : A polyketide isolated from the bark of Asimina triloba. It has been shown to exhibit cytotoxicity in the NCI human tumor cell line screen.		1.9910butenolide;
polyketide;
triol		antineoplastic agent;
plant metabolite
10-hydroxyasimicin
10-hydroxyasimicin: a bis-tetrahydrofuran acetogenin with 4 hydroxyl groups; from Asimina triloba; structure given in first source		1.9910
ConditionIndicatedRelationship StrengthStudiesTrials
Benign Neoplasms
[description not available]		02.0710
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.		02.0710
Colorectal Cancer
[description not available]		07.110
Colorectal Neoplasms
Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.		02.110