CHEBI:40303 - lovastatin

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ChEBI Name lovastatin
ChEBI ID CHEBI:40303
Definition 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).
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:40299, CHEBI:6544
Supplier Information ChemicalBook:CB5159244, eMolecules:474218
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Oxygen is a chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and a potent oxidizing agent that readily forms oxides with most elements as well as with other compounds. Oxygen is the most abundant element in Earth's crust, and the third-most abundant element in the universe after hydrogen and helium. At standard temperature and pressure, two oxygen atoms will bind covalently to form dioxygen, a colorless and odorless diatomic gas with the chemical formula O2. Dioxygen gas currently constitutes approximately 20.95% molar fraction of the Earth's atmosphere, though this has changed considerably over long periods of time in Earth's history. Oxygen makes up almost half of the Earth's crust in the form of various oxides such as water, carbon dioxide, iron oxides and silicates. All eukaryotic organisms, including plants, animals, fungi, algae and most protists, need oxygen for cellular respiration, which extracts chemical energy by the reaction of oxygen with organic molecules derived from food and releases carbon dioxide as a waste product. In aquatic animals, dissolved oxygen in water is absorbed by specialized respiratory organs called gills, through the skin or via the gut; in terrestrial animals such as tetrapods, oxygen in air is actively taken into the body via specialized organs known as lungs, where gas exchange takes place to diffuse oxygen into the blood and carbon dioxide out, and the body's circulatory system then transports the oxygen to other tissues where cellular respiration takes place. However in insects, the most successful and biodiverse terrestrial clade, oxygen is directly conducted to the internal tissues via a deep network of airways. Many major classes of organic molecules in living organisms contain oxygen atoms, such as proteins, nucleic acids, carbohydrates and fats, as do the major constituent inorganic compounds of animal shells, teeth, and bone. Most of the mass of living organisms is oxygen as a component of water, the major constituent of lifeforms. Oxygen in Earth's atmosphere is produced by biotic photosynthesis, in which photon energy in sunlight is captured by chlorophyll to split water molecules and then react with carbon dioxide to produce carbohydrates and oxygen is released as a byproduct. Oxygen is too chemically reactive to remain a free element in air without being continuously replenished by the photosynthetic activities of autotrophs such as cyanobacteria, chloroplast-bearing algae and plants. A much rarer triatomic allotrope of oxygen, ozone (O3), strongly absorbs the UVB and UVC wavelengths and forms a protective ozone layer at the lower stratosphere, which shields the biosphere from ionizing ultraviolet radiation. However, ozone present at the surface is a corrosive byproduct of smog and thus an air pollutant. Oxygen was isolated by Michael Sendivogius before 1604, but it is commonly believed that the element was discovered independently by Carl Wilhelm Scheele, in Uppsala, in 1773 or earlier, and Joseph Priestley in Wiltshire, in 1774. Priority is often given for Priestley because his work was published first. Priestley, however, called oxygen "dephlogisticated air", and did not recognize it as a chemical element. The name oxygen was coined in 1777 by Antoine Lavoisier, who first recognized oxygen as a chemical element and correctly characterized the role it plays in combustion. Common industrial uses of oxygen include production of steel, plastics and textiles, brazing, welding and cutting of steels and other metals, rocket propellant, oxygen therapy, and life support systems in aircraft, submarines, spaceflight and diving.
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Formula C24H36O5
Net Charge 0
Average Mass 404.53964
Monoisotopic Mass 404.25627
InChI InChI=1S/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1
InChIKey PCZOHLXUXFIOCF-BXMDZJJMSA-N
SMILES [H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)[C@@H](C)CC
Roles Classification
Biological Role(s): Aspergillus metabolite
Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via statin (naturally occurring) )
EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor
Any EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that inhibits HMG-CoA reductases. Hydroxymethylglutaryl-CoA reductase inhibitors have been shown to lower directly cholesterol synthesis. The Enzyme Commission designation is EC 1.1.1.34 for the NADPH-dependent enzyme and EC 1.1.1.88 for an NADH-dependent enzyme.
(via statin )
Application(s): prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
anticholesteremic drug
A substance used to lower plasma cholesterol levels.
(via statin )
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing lovastatin (CHEBI:40303) has functional parent (S)-2-methylbutyric acid (CHEBI:38655)
lovastatin (CHEBI:40303) has functional parent mevastatin (CHEBI:34848)
lovastatin (CHEBI:40303) has role Aspergillus metabolite (CHEBI:76956)
lovastatin (CHEBI:40303) has role anticholesteremic drug (CHEBI:35821)
lovastatin (CHEBI:40303) has role antineoplastic agent (CHEBI:35610)
lovastatin (CHEBI:40303) has role prodrug (CHEBI:50266)
lovastatin (CHEBI:40303) is a δ-lactone (CHEBI:18946)
lovastatin (CHEBI:40303) is a fatty acid ester (CHEBI:35748)
lovastatin (CHEBI:40303) is a hexahydronaphthalenes (CHEBI:142348)
lovastatin (CHEBI:40303) is a polyketide (CHEBI:26188)
lovastatin (CHEBI:40303) is a statin (naturally occurring) (CHEBI:87632)
Incoming mevinolinic acid (CHEBI:82985) has functional parent lovastatin (CHEBI:40303)
simvastatin (CHEBI:9150) has functional parent lovastatin (CHEBI:40303)
xuezhikang (CHEBI:231891) has part lovastatin (CHEBI:40303)
IUPAC Name
(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate
Synonyms Sources
(1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(2R,4R)-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl (S)-2-methyl-butyrate ChemIDplus
2β,6α-dimethyl-8alpha-(2-methyl-1-oxobutoxy)-mevinic acid lactone ChemIDplus
6α-methylcompactin ChemIDplus
Lovastatin KEGG COMPOUND
LOVASTATIN PDBeChem
lovastatin UniProt
Mevinolin ChemIDplus
MK-803 KEGG DRUG
ML-530B KEGG DRUG
Brand Name Source
Mevacor ChemIDplus
Manual Xrefs Databases
1612 DrugCentral
803 PDBeChem
C00000547 KNApSAcK
C07074 KEGG COMPOUND
CN103172602 Patent
D00359 KEGG DRUG
DB00227 DrugBank
HMDB0014372 HMDB
Lovastatin Wikipedia
LSM-2189 LINCS
WO2013090461 Patent
View more database links
Registry Numbers Types Sources
3631989 Beilstein Registry Number ChemIDplus
4720754 Reaxys Registry Number Reaxys
75330-75-5 CAS Registry Number ChemIDplus
75330-75-5 CAS Registry Number KEGG DRUG
Citations Types Sources
11375168 PubMed citation Europe PMC
11389707 PubMed citation Europe PMC
11483865 PubMed citation Europe PMC
18642339 PubMed citation Europe PMC
24093797 PubMed citation Europe PMC
7720768 PubMed citation Europe PMC
Last Modified
05 September 2024