CHEBI:42111 - (R)-lactic acid

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ChEBI Name (R)-lactic acid
ChEBI ID CHEBI:42111
ChEBI ASCII Name (R)-lactic acid
Definition An optically active form of lactic acid having (R)-configuration.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42105, CHEBI:43701, CHEBI:341
Supplier Information ChemicalBook:CB02550000, ChemicalBook:CB22515128, eMolecules:32176418, Selleckchem:PLX-4032, ZINC000052509366
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Aldosterone is the main mineralocorticoid steroid hormone produced by the zona glomerulosa of the adrenal cortex in the adrenal gland. It is essential for sodium conservation in the kidney, salivary glands, sweat glands, and colon. It plays a central role in the homeostatic regulation of blood pressure, plasma sodium (Na+), and potassium (K+) levels. It does so primarily by acting on the mineralocorticoid receptors in the distal tubules and collecting ducts of the nephron. It influences the reabsorption of sodium and excretion of potassium (from and into the tubular fluids, respectively) of the kidney, thereby indirectly influencing water retention or loss, blood pressure, and blood volume. When dysregulated, aldosterone is pathogenic and contributes to the development and progression of cardiovascular and kidney disease. Aldosterone has exactly the opposite function of the atrial natriuretic hormone secreted by the heart. Aldosterone is part of the renin–angiotensin–aldosterone system. It has a plasma half-life of less than 20 minutes. Drugs that interfere with the secretion or action of aldosterone are in use as antihypertensives, like lisinopril, which lowers blood pressure by blocking the angiotensin-converting enzyme (ACE), leading to lower aldosterone secretion. The net effect of these drugs is to reduce sodium and water retention but increase the retention of potassium. In other words, these drugs stimulate the excretion of sodium and water in urine, while they block the excretion of potassium. Another example is spironolactone, a potassium-sparing diuretic of the steroidal spirolactone group, which interferes with the aldosterone receptor (among others) leading to lower blood pressure by the mechanism described above. Aldosterone was first isolated by Sylvia Tait (Simpson) and Jim Tait in 1953; in collaboration with Tadeusz Reichstein.
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Formula C3H6O3
Net Charge 0
Average Mass 90.07794
Monoisotopic Mass 90.03169
InChI InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m1/s1
InChIKey JVTAAEKCZFNVCJ-UWTATZPHSA-N
SMILES C[C@@H](O)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
(via 2-hydroxypropanoic acid )
Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
(via 2-hydroxypropanoic acid )
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ChEBI Ontology
Outgoing (R)-lactic acid (CHEBI:42111) has role Escherichia coli metabolite (CHEBI:76971)
(R)-lactic acid (CHEBI:42111) has role human metabolite (CHEBI:77746)
(R)-lactic acid (CHEBI:42111) is a 2-hydroxypropanoic acid (CHEBI:78320)
(R)-lactic acid (CHEBI:42111) is conjugate acid of (R)-lactate (CHEBI:16004)
(R)-lactic acid (CHEBI:42111) is enantiomer of (S)-lactic acid (CHEBI:422)
Incoming (R)-S-lactoylglutathione (CHEBI:15694) has functional parent (R)-lactic acid (CHEBI:42111)
(R)-lactoyl-CoA (CHEBI:71164) has functional parent (R)-lactic acid (CHEBI:42111)
D-alanyl-(R)-lactic acid (CHEBI:61163) has functional parent (R)-lactic acid (CHEBI:42111)
D-prephenyl lactate (CHEBI:27441) has functional parent (R)-lactic acid (CHEBI:42111)
ethyl (2R)-lactate (CHEBI:78323) has functional parent (R)-lactic acid (CHEBI:42111)
methyl (R)-lactate (CHEBI:74611) has functional parent (R)-lactic acid (CHEBI:42111)
rac-lactic acid (CHEBI:28358) has part (R)-lactic acid (CHEBI:42111)
(R)-lactate (CHEBI:16004) is conjugate base of (R)-lactic acid (CHEBI:42111)
(S)-lactic acid (CHEBI:422) is enantiomer of (R)-lactic acid (CHEBI:42111)
(R)-lactoyl group (CHEBI:149487) is substituent group from (R)-lactic acid (CHEBI:42111)
IUPAC Name
(2R)-2-hydroxypropanoic acid
Synonyms Sources
(−)-lactic acid ChemIDplus
(R)-(−)-lactic acid ChemIDplus
D-2-Hydroxypropanoic acid KEGG COMPOUND
D-2-Hydroxypropionic acid KEGG COMPOUND
D-lactic acid ChemIDplus
D-Lactic acid KEGG COMPOUND
D-Milchsäure ChEBI
LACTIC ACID PDBeChem
Manual Xrefs Databases
C00019549 KNApSAcK
C00256 KEGG COMPOUND
DB03066 DrugBank
DB04398 DrugBank
HMDB0001311 HMDB
LAC PDBeChem
Lactic_acid Wikipedia
View more database links
Registry Numbers Types Sources
10326-41-7 CAS Registry Number KEGG COMPOUND
10326-41-7 CAS Registry Number ChemIDplus
1720252 Beilstein Registry Number Beilstein
1720252 Reaxys Registry Number Reaxys
362718 Gmelin Registry Number Gmelin
Citations Types Sources
21842515 PubMed citation Europe PMC
22127808 PubMed citation Europe PMC
22277286 PubMed citation Europe PMC
22344644 PubMed citation Europe PMC
Last Modified
23 October 2015