CHEBI:30089 - acetate

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ChEBI Name acetate
ChEBI ID CHEBI:30089
Definition A monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of acetic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:40480, CHEBI:13704, CHEBI:22165
Supplier Information eMolecules:27517656, eMolecules:493944, ZINC000000001084
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Caffeine is a central nervous system (CNS) stimulant of the methylxanthine class and is the most commonly consumed psychoactive substance globally. It is mainly used for its eugeroic (wakefulness promoting), ergogenic (physical performance-enhancing), or nootropic (cognitive-enhancing) properties. Caffeine acts by blocking binding of adenosine at a number of adenosine receptor types, inhibiting the centrally depressant effects of adenosine and enhancing the release of acetylcholine. Caffeine has a three-dimensional structure similar to that of adenosine, which allows it to bind and block its receptors. Caffeine also increases cyclic AMP levels through nonselective inhibition of phosphodiesterase, increases calcium release from intracellular stores, and antagonizes GABA receptors, although these mechanisms typically occur at concentrations beyond usual human consumption. Caffeine is a bitter, white crystalline purine, a methylxanthine alkaloid, and is chemically related to the adenine and guanine bases of deoxyribonucleic acid (DNA) and ribonucleic acid (RNA). It is found in the seeds, fruits, nuts, or leaves of a number of plants native to Africa, East Asia and South America and helps to protect them against herbivores and from competition by preventing the germination of nearby seeds, as well as encouraging consumption by select animals such as honey bees. The best-known source of caffeine is the coffee bean, the seed of the Coffea plant. People may drink beverages containing caffeine to relieve or prevent drowsiness and to improve cognitive performance. To make these drinks, caffeine is extracted by steeping the plant product in water, a process called infusion. Caffeine-containing drinks, such as coffee, tea, and cola, are consumed globally in high volumes. In 2020, almost 10 million tonnes of coffee beans were consumed globally. Caffeine is the world's most widely consumed psychoactive drug. Unlike most other psychoactive substances, caffeine remains largely unregulated and legal in nearly all parts of the world. Caffeine is also an outlier as its use is seen as socially acceptable in most cultures with it even being encouraged. Caffeine has both positive and negative health effects. It can treat and prevent the premature infant breathing disorders bronchopulmonary dysplasia of prematurity and apnea of prematurity. Caffeine citrate is on the WHO Model List of Essential Medicines. It may confer a modest protective effect against some diseases, including Parkinson's disease. Some people experience sleep disruption or anxiety if they consume caffeine, but others show little disturbance. Evidence of a risk during pregnancy is equivocal; some authorities recommend that pregnant women limit caffeine to the equivalent of two cups of coffee per day or less. Caffeine can produce a mild form of drug dependence – associated with withdrawal symptoms such as sleepiness, headache, and irritability – when an individual stops using caffeine after repeated daily intake. Tolerance to the autonomic effects of increased blood pressure and heart rate, and increased urine output, develops with chronic use (i.e., these symptoms become less pronounced or do not occur following consistent use). Caffeine is classified by the U.S. Food and Drug Administration (FDA) as generally recognized as safe. Toxic doses, over 10 grams per day for an adult, are much higher than the typical dose of under 500 milligrams per day. The European Food Safety Authority reported that up to 400 mg of caffeine per day (around 5.7 mg/kg of body mass per day) does not raise safety concerns for non-pregnant adults, while intakes up to 200 mg per day for pregnant and lactating women do not raise safety concerns for the fetus or the breast-fed infants. A cup of coffee contains 80–175 mg of caffeine, depending on what "bean" (seed) is used, how it is roasted, and how it is prepared (e.g., drip, percolation, or espresso). Thus it requires roughly 50–100 ordinary cups of coffee to reach the toxic dose. However, pure powdered caffeine, which is available as a dietary supplement, can be lethal in tablespoon-sized amounts.
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Formula C2H3O2
Net Charge -1
Average Mass 59.04402
Monoisotopic Mass 59.01385
InChI InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)/p-1
InChIKey QTBSBXVTEAMEQO-UHFFFAOYSA-M
SMILES CC([O-])=O
Metabolite of Species Details
Saccharomyces cerevisiae (NCBI:txid4932) Source: yeast.sf.net See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
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ChEBI Ontology
Outgoing acetate (CHEBI:30089) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
acetate (CHEBI:30089) has role human metabolite (CHEBI:77746)
acetate (CHEBI:30089) is a monocarboxylic acid anion (CHEBI:35757)
acetate (CHEBI:30089) is conjugate base of acetic acid (CHEBI:15366)
Incoming (2,2,3-trimethyl-5-oxocyclopent-3-en-1-yl)acetate (CHEBI:19733) has functional parent acetate (CHEBI:30089)
(2,6-dihydroxyphenyl)acetate (CHEBI:28440) has functional parent acetate (CHEBI:30089)
(5-oxo-2-sulfonato-2,5-dihydrofuran-2-yl)acetate (CHEBI:20479) has functional parent acetate (CHEBI:30089)
1-palmityl-2-acetyl-sn-glycero-3-phosphate(2−) (CHEBI:78385) has functional parent acetate (CHEBI:30089)
4-chlorophenylacetate (CHEBI:16237) has functional parent acetate (CHEBI:30089)
4-hydroxyphenylacetate (CHEBI:48999) has functional parent acetate (CHEBI:30089)
chloroacetate (CHEBI:23123) has functional parent acetate (CHEBI:30089)
dichloroacetate (CHEBI:28240) has functional parent acetate (CHEBI:30089)
difluoroacetate (CHEBI:23715) has functional parent acetate (CHEBI:30089)
fluoroacetate (CHEBI:18172) has functional parent acetate (CHEBI:30089)
glycolate (CHEBI:29805) has functional parent acetate (CHEBI:30089)
haloacetate(1−) (CHEBI:85638) has functional parent acetate (CHEBI:30089)
homogentisate (CHEBI:16169) has functional parent acetate (CHEBI:30089)
mandelate (CHEBI:25147) has functional parent acetate (CHEBI:30089)
phenylacetate (CHEBI:18401) has functional parent acetate (CHEBI:30089)
trichloroacetate (CHEBI:27455) has functional parent acetate (CHEBI:30089)
trifluoroacetate (CHEBI:27110) has functional parent acetate (CHEBI:30089)
calcium acetate (CHEBI:3310) has part acetate (CHEBI:30089)
ethylammonium acetate (CHEBI:63879) has part acetate (CHEBI:30089)
guanidine acetate (CHEBI:132481) has part acetate (CHEBI:30089)
lead tetraacetate (CHEBI:77245) has part acetate (CHEBI:30089)
lithium acetate (CHEBI:63045) has part acetate (CHEBI:30089)
potassium acetate (CHEBI:32029) has part acetate (CHEBI:30089)
sodium acetate (CHEBI:32954) has part acetate (CHEBI:30089)
acetic acid (CHEBI:15366) is conjugate acid of acetate (CHEBI:30089)
IUPAC Name
acetate
Synonyms Sources
acetate UniProt
ACETATE ION PDBeChem
acetic acid, ion(1−) ChemIDplus
Azetat ChEBI
CH3‒COO IUPAC
Ethanoat ChEBI
ethanoate ChEBI
MeCO2 anion NIST Chemistry WebBook
Manual Xrefs Databases
ACET MetaCyc
Acetate Wikipedia
ACT PDBeChem
C00033 KEGG COMPOUND
c0050 UM-BBD
DB03166 DrugBank
View more database links
Registry Numbers Types Sources
1379 Gmelin Registry Number Gmelin
1901470 Reaxys Registry Number Reaxys
71-50-1 CAS Registry Number NIST Chemistry WebBook
71-50-1 CAS Registry Number ChemIDplus
Citations Types Sources
17190852 PubMed citation Europe PMC
22211106 PubMed citation Europe PMC
22371380 PubMed citation Europe PMC
Last Modified
13 January 2017