Compounds > 6-fluoromevalonolactone
Page last updated: 2024-12-07

6-fluoromevalonolactone

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

6-Fluoromevalonolactone is a synthetic analog of mevalonolactone, a key intermediate in the biosynthesis of cholesterol and other isoprenoids. It acts as a potent inhibitor of hydroxymethylglutaryl-CoA reductase (HMG-CoA reductase), the rate-limiting enzyme in cholesterol biosynthesis. Due to its ability to block cholesterol synthesis, 6-fluoromevalonolactone has been investigated as a potential therapeutic agent for hypercholesterolemia and other cardiovascular diseases. The compound has also been studied for its potential anti-inflammatory and anti-cancer properties. Synthesis of 6-fluoromevalonolactone typically involves fluorination of mevalonolactone or a suitable precursor. The compound is often used in research to study the regulation of cholesterol biosynthesis and the effects of HMG-CoA reductase inhibition.'
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Cross-References

ID SourceID
PubMed CID119214
CHEMBL ID3185156
CHEBI ID125368
MeSH IDM0131500

Synonyms (20)

Synonym
4-(fluoromethyl)tetrahydro-4-hydroxy-2h-pyran-2-one
6-fluoromevalonate, >=90% (gc), viscous liquid
NCGC00165794-01
fluoromevalonate
CHEBI:125368
2822-77-7
4-(fluoromethyl)-4-hydroxyoxan-2-one
AKOS006285000
2h-pyran-2-one, 4-(fluoromethyl)tetrahydro-4-hydroxy-
6-fmva
6-fluoromevalonate
6-fluoromevalonolactone
zr 3516
BRD-A12426960-001-01-6
CHEMBL3185156
4-(fluoromethyl)-4-hydroxy-2-oxanone
Q27215723
J-017007
CS-0135985
HY-133957
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
delta-lactoneA lactone having a six-membered lactone ring.
[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]

Protein Targets (1)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency1.00000.003245.467312,589.2998AID2517
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (22.22)18.7374
1990's6 (66.67)18.2507
2000's0 (0.00)29.6817
2010's1 (11.11)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: 12.27

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 Index12.27 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.27)

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%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
isopentenyl pyrophosphate
isopentenyl pyrophosphate: substrate for isopentenyl pyrophosphate isomerase; RN given refers to unlabeled cpd; a nonpeptide mycobacterial antigen that stimulates gamma delta T cells. isopentenyl diphosphate : A prenol phosphate comprising 3-methylbut-3-en-1-ol having an O-diphosphate substituent.		1.9610prenol phosphateantigen;
antioxidant;
epitope;
Escherichia coli metabolite;
mouse metabolite;
phosphoantigen
pamidronate
[no description available]		2.0610phosphonoacetic acid
thymidine
[no description available]		1.9810pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
cantharidin
Cantharidin: A toxic compound, isolated from the Spanish fly or blistering beetle (Lytta (Cantharis) vesicatoria) and other insects. It is a potent and specific inhibitor of protein phosphatases 1 (PP1) and 2A (PP2A). This compound can produce severe skin inflammation, and is extremely toxic if ingested orally.. cantharidin : A monoterpenoid with an epoxy-bridged cyclic dicarboxylic anhydride structure secreted by many species of blister beetle, and most notably by the Spanish fly, Lytta vesicatoria. Natural toxin inhibitor of protein phosphatases 1 and 2A.		1.9610cyclic dicarboxylic anhydride;
monoterpenoid		EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor;
herbicide
thiophenes
Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.		1.9910mancude organic heteromonocyclic parent;
monocyclic heteroarene;
thiophenes;
volatile organic compound		non-polar solvent
lovastatin
Lovastatin: A fungal metabolite isolated from cultures of Aspergillus terreus. The compound is a potent anticholesteremic agent. It inhibits 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It also stimulates the production of low-density lipoprotein receptors in the liver.. lovastatin : A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom).		2.940delta-lactone;
fatty acid ester;
hexahydronaphthalenes;
polyketide;
statin (naturally occurring)		anticholesteremic drug;
antineoplastic agent;
Aspergillus metabolite;
prodrug
zoledronic acid
Zoledronic Acid: An imidobisphosphonate inhibitor of BONE RESORPTION that is used for the treatment of malignancy-related HYPERCALCEMIA; OSTEITIS DEFORMANS; and OSTEOPOROSIS.. zoledronic acid : An imidazole compound having a 2,2-bis(phosphono)-2-hydroxyethane-1-yl substituent at the 1-position.		2.06101,1-bis(phosphonic acid);
imidazoles		bone density conservation agent
mevalonic acid
Mevalonic Acid: A dihydroxy monocarboxylic acid and precursor in the biosynthetic pathway known as the mevalonate pathway, which produces terpenes and steroids that are vital for diverse cellular functions.. mevalonic acid : A racemate composed of equimolar amounts of (R)- and (S)-mevalonic acid.. (R)-mevalonic acid : The (R)-enantiomer of mevalonic acid.		3.59903,5-dihydroxy-3-methylpentanoic acid
5-diphosphomevalonic acid
5-diphosphomevalonic acid: RN given refers to ion(1-). (R)-5-diphosphomevalonic acid : The 5-diphospho derivative of (R)-mevalonic acid.		2.3820carboxyalkyl phosphatehuman metabolite;
mouse metabolite
squalestatin 1
squalestatin 1: structure given in first source; inhibits both mammalian and fungal squalene synthetase; from fungus Phoma sp (Coelomycetes). zaragozic acid A : A polyketide isolated from fungi that is a potent inhibitor of fungal and mammalian squalene synthase.		2.4220acetate ester;
cyclic ketal;
oxabicycloalkane;
polyketide;
tertiary alcohol;
tricarboxylic acid		EC 2.5.1.21 (squalene synthase) inhibitor;
fungal metabolite
nb 598
NB 598: decreases serum total & LDL-cholesterol levels; structure given in first source; inhibits squalene epoxidase		1.9910
ConditionIndicatedRelationship StrengthStudiesTrials
Bladder Cancer
[description not available]		01.9810
Cell Transformation, Neoplastic
Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.		01.9810
Urinary Bladder Neoplasms
Tumors or cancer of the URINARY BLADDER.		01.9810
Hepatocellular Carcinoma
[description not available]		01.9910
Cancer of Liver
[description not available]		01.9910
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.		01.9910
Liver Neoplasms
Tumors or cancer of the LIVER.		01.9910