ChemFOnt: Showing chemical card for L-Lactic acid (CFc000000122)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:26 UTC

Chemfont ID

CFc000000122

Molecule Identification

Common Name

L-Lactic acid

Definition

Lactic acid is an organic acid. It is a chiral molecule, consisting of two optical isomers, L-lactic acid and D-lactic acid, with the L-isomer being the most common in living organisms. Lactic acid plays a role in several biochemical processes and is produced in the muscles during intense activity. In animals, L-lactate is constantly produced from pyruvate via the enzyme lactate dehydrogenase (LDH) in a process of fermentation during normal metabolism and exercise. It does not increase in concentration until the rate of lactate production exceeds the rate of lactate removal. This is governed by a number of factors, including monocarboxylate transporters, lactate concentration, the isoform of LDH, and oxidative capacity of tissues. The concentration of blood lactate is usually 1-2 mmol/L at rest, but can rise briefly to over 20 mmol/L during intense exertion. There are some indications that lactate, and not glucose, is preferentially metabolized by neurons in the brain of several mammalian species, including mice, rats, and humans. Glial cells, using the lactate shuttle, are responsible for transforming glucose into lactate, and for providing lactate to the neurons. Lactate measurement in critically ill patients has been traditionally used to stratify patients with poor outcomes. In particular, resting lactate levels > 2.0 mM are commonly used to identify patients developing sepsis or lactic acidosis (PMID: 27501243 ). In fact, risk for mortality from sepsis or trauma rises with lactate levels with concentrations of >4.0 mM being particularly dangerous (PMID: 27501243 ). However, plasma lactate levels are the result of a finely tuned interplay of factors that affect the balance between its production and its clearance. When the oxygen supply does not match its consumption, organisms adapt in many different ways, up to the point when energy failure occurs. Lactate, being part of the adaptive response, may then be used to assess the severity of the supply/demand imbalance. In such a scenario, the time to intervention becomes relevant: early and effective treatment may allow tissues and cells to revert to a normal state, as long as the oxygen machinery (i.e. mitochondria) is intact. Conversely, once the mitochondria are deranged, energy failure occurs even in the presence of normoxia. The lactate increase in critically ill patients may, therefore, be viewed as an early marker of a potentially reversible state (PMID: 16356243 ). When present in sufficiently high levels, lactic acid can act as an oncometabolite, an immunosuppressant, an acidogen, and a metabotoxin. An oncometabolite is a compound that promotes tumor growth and survival. An immunosuppressant reduces or arrests the activity of the immune system. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of lactic acid are associated with at least a dozen inborn errors of metabolism, including 2-methyl-3-hydroxybutyryl CoA dehydrogenase deficiency, biotinidase deficiency, fructose-1,6-diphosphatase deficiency, glycogen storage disease type 1A (GSD1A) or Von Gierke disease, glycogenosis type IB, glycogenosis type IC, glycogenosis type VI, Hers disease, lactic acidemia, Leigh syndrome, methylmalonate semialdehyde dehydrogenase deficiency, pyruvate decarboxylase E1 component deficiency, pyruvate dehydrogenase complex deficiency, pyruvate dehydrogenase deficiency, and short chain acyl CoA dehydrogenase deficiency (SCAD deficiency). Locally high concentrations of lactic acid or lactate are found near many tumors due to the upregulation of lactate dehydrogenase (PMID: 15279558 ). Lactic acid produced by tumors through aerobic glycolysis acts as an immunosuppressant and tumor promoter (PMID: 23729358 ). Indeed, lactic acid has been found to be a key player or regulator in the development and malignant progression of a variety of cancers (PMID: 22084445 ). A number of studies have demonstrated that malignant transformation is associated with an increase in aerobic cellular lactate excretion. Lactate concentrations in various carcinomas (e.g. uterine cervix, head and neck, colorectal region) at first diagnosis of the disease, can be relatively low or extremely high (up to 40 µmol/g) in different individual tumors or within the same lesion (PMID: 15279558 ). High molar concentrations of lactate are correlated with a high incidence of distant metastasis. Low lactate tumors (< median of approximately 8 µmol/g) are associated with both an overall longer and disease-free survival compared to high lactate lesions (lactate > approximately 8 µmol/g). Lactate-induced secretion of hyaluronan by tumor-associated fibroblasts creates a milieu favourable for cell migration and metastases (PMID: 22084445 ). An acidic environment (pH 6-6.5), which is common in many tumors, allows tumor cells to evade the immune response, and therefore allows them to grow unchecked. Locally high concentrations of lactic acid are known to markedly impede the function of normal immune cells and will lead to a loss of T-cell function of human tumor-infiltrating lymphocytes (PMID: 22084445 ). Lactic acid is also an organic acid and acts as a general acidogen. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart abnormalities, kidney abnormalities, liver damage, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. Lactic acid is also a microbial metabolite. Urinary lactic acid is produced by Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Enterobacter, Acinetobacter, Proteus mirabilis, Citrobacter frundii, Enterococcus faecalis, Streptococcus group B, Staphylococcus saprophyticus (PMID: 22292465 ), Bacillus, Corynebacterium, Rhizopus and Saccharomyces cerevisiae (PMID: 26360870 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-Lactic acid	ChEBI
(S)-(+)-Lactic acid	ChEBI
(S)-2-Hydroxypropanoic acid	ChEBI
(S)-2-Hydroxypropionic acid	ChEBI
L-(+)-alpha-Hydroxypropionic acid	ChEBI
L-(+)-Lactic acid	ChEBI
L-Milchsaeure	ChEBI
L-Lactate	Kegg
(+)-Lactate	Generator
(S)-(+)-Lactate	Generator
(S)-2-Hydroxypropanoate	Generator
(S)-2-Hydroxypropionate	Generator
L-(+)-a-Hydroxypropionate	Generator
L-(+)-a-Hydroxypropionic acid	Generator
L-(+)-alpha-Hydroxypropionate	Generator
L-(+)-Α-hydroxypropionate	Generator
L-(+)-Α-hydroxypropionic acid	Generator
L-(+)-Lactate	Generator
(alpha)-Lactate	HMDB
(alpha)-Lactic acid	HMDB
(S)-(+)-2-Hydroxypropanoate	HMDB
(S)-(+)-2-Hydroxypropanoic acid	HMDB
(S)-2-Hydroxy-propanoate	HMDB
(S)-2-Hydroxy-propanoic acid	HMDB
(S)-Lactate	HMDB
(S)-Lactic acid	HMDB
1-Hydroxyethane 1-carboxylate	HMDB
1-Hydroxyethane 1-carboxylic acid	HMDB
1-Hydroxyethanecarboxylate	HMDB
1-Hydroxyethanecarboxylic acid	HMDB
2-Hydroxypropanoate	HMDB
2-Hydroxypropanoic acid	HMDB
2-Hydroxypropionate	HMDB
a-Hydroxypropanoate	HMDB
a-Hydroxypropanoic acid	HMDB
a-Hydroxypropionate	HMDB
a-Hydroxypropionic acid	HMDB
alpha-Hydroxypropanoate	HMDB
alpha-Hydroxypropanoic acid	HMDB
alpha-Hydroxypropionate	HMDB
alpha-Hydroxypropionic acid	HMDB
L-(+)- Lactic acid	HMDB
L-2-Hydroxypropanoate	HMDB
L-2-Hydroxypropanoic acid	HMDB
Lactate	HMDB
Lactic acid	HMDB
Milk acid	HMDB
Sarcolactic acid	HMDB
2-Hydroxypropionic acid	HMDB
D-Lactic acid	HMDB
D Lactic acid	HMDB
Lactate, ammonium	HMDB
2 Hydroxypropanoic acid	HMDB
2 Hydroxypropionic acid	HMDB
Ammonium lactate	HMDB
L Lactic acid	HMDB
D-Lactate	HMDB
L-Lactic acid	ChEBI

Chemical Formula

C₃H₆O₃

Average Molecular Weight

90.0779

Monoisotopic Molecular Weight

90.031694058

IUPAC Name

(2S)-2-hydroxypropanoic acid

Traditional Name

(α)-lactate

CAS Registry Number

79-33-4

SMILES

C[C@H](O)C(O)=O

InChI Identifier

InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1

InChI Key

JVTAAEKCZFNVCJ-REOHCLBHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Alpha hydroxy acids and derivatives

Direct Parent

Alpha hydroxy acids and derivatives

Alternative Parents

Substituents

Alpha-hydroxy acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-hydroxypropanoic acid (CHEBI:422 )

Functional Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16324927)
Breast milk (PMID: 24027187)
Cerebrospinal Fluid (CSF) (PMID: 15627241)
Bile (PMID: 15780050)
Cellular Cytoplasm (PMID: 15882454)
Saliva (PMID: 22308371)

Tissue

All Tissues (HMDB: HMDB0000190)

Organ

Placenta (HMDB: HMDB0000190)

Excreta

Biofluid or Excreta

Urine (PMID: 9625050)
Feces (PMID: 18052033)
Sweat (PMID: 22194922)

Cellular substructure

Cytoplasm (HMDB: HMDB0000190)
Extracellular (HMDB: HMDB0000190)

Organelle

Mitochondrion (HMDB: HMDB0000190)

Source

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Pyruvate Metabolism (HMDB: HMDB0000190)
Gluconeogenesis (HMDB: HMDB0000190)
Warburg Effect (PathBank: SMP0087270)
L-Lactaldehyde Degradation (Aerobic) (PathBank: SMP0122245)
Methylglyoxal Degradation I (PathBank: SMP0122266)
Methylglyoxal Degradation IV (PathBank: SMP0122246)
Fucose and Rhamnose Degradation (PathBank: SMP0000846)

Disease pathway

Fructose-1,6-diphosphatase Deficiency (HMDB: HMDB0000190)
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke Disease (HMDB: HMDB0000190)
2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency (HMDB: HMDB0000190)
Lactic Acidemia (HMDB: HMDB0000190)
Biotinidase Deficiency (HMDB: HMDB0000190)
Pyruvate Dehydrogenase Complex Deficiency (HMDB: HMDB0000190)
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency) (HMDB: HMDB0000190)
Methylmalonate Semialdehyde Dehydrogenase Deficiency (HMDB: HMDB0000190)
Pyruvate Dehydrogenase Deficiency (E2) (HMDB: HMDB0000190)
Glycogenosis, Type IB (HMDB: HMDB0000190)
Glycogenosis, Type IC (HMDB: HMDB0000190)
Leigh Syndrome (HMDB: HMDB0000190)
Short-Chain Acyl-CoA Dehydrogenase Deficiency (SCAD Deficiency) (HMDB: HMDB0000190)
Glycogenosis, Type VI. Hers Disease (HMDB: HMDB0000190)
Glutaminolysis and Cancer (PathBank: SMP0108773)
Glycogenosis, Type IA. Von Gierke Disease (PathBank: SMP0120864)
Pyruvate Kinase Deficiency (PathBank: SMP0120623)
Primary Hyperoxaluria II, PH2 (PathBank: SMP0120841)
Phosphoenolpyruvate Carboxykinase Deficiency 1 (PEPCK1) (PathBank: SMP0120843)
Triosephosphate Isomerase Deficiency (PathBank: SMP0120846)

Role

Biological role

Human metabolite (HMDB: HMDB0000190)
Escherichia coli metabolite (HMDB: HMDB0000190)
Waste product (PMID: 35448883)

Industrial application

Pharmaceutical industry

Biomarker

Preeclampsia/Eclampsia (MarkerDB: MDB00000090)
Alzheimer's Disease (MarkerDB: MDB00000090)
Diabetes mellitus type 2 (MarkerDB: MDB00000090)
Eosinophilic esophagitis (MarkerDB: MDB00000090)
Paraquat poisoning (MarkerDB: MDB00000090)
Type V 3-Methylglutaconic Aciduria (MarkerDB: MDB00000090)
Propionic acidemia (MarkerDB: MDB00000090)
Autosomal dominant polycystic kidney disease (MarkerDB: MDB00000090)
Epilepsy (MarkerDB: MDB00000090)
Hereditary Fructose Intolerance (MarkerDB: MDB00000090)
Amish Type Microcephaly (MarkerDB: MDB00000090)
Pyruvate Dehydrogenase Phosphatase Deficiency (MarkerDB: MDB00000090)
Pearson Marrow Pancreas Syndrome (MarkerDB: MDB00000090)
Pyruvate Dehydrogenase Deficiency (MarkerDB: MDB00000090)
Pyruvate carboxylase deficiency (MarkerDB: MDB00000090)
Coenzyme Q10 Deficiency (MarkerDB: MDB00000090)
Cytochrome C oxidase deficiency (MarkerDB: MDB00000090)
Leber Optic Atrophy And Dystonia (MarkerDB: MDB00000090)
Leigh syndrome (MarkerDB: MDB00000090)
Mitochondrial Phosphate Carrier Deficiency (MarkerDB: MDB00000090)
3 Hydroxyacyl Co A Dehydrogenase Deficiency (MarkerDB: MDB00000090)
G.R.A.C.I.L.E. Syndrome (MarkerDB: MDB00000090)
Hereditary Myopathy With Lactic Acidosis (MarkerDB: MDB00000090)
Acute Infantile Liver Failure (MarkerDB: MDB00000090)
Fructose 1,6 Bisphosphatase Deficiency (MarkerDB: MDB00000090)
MLASA (MarkerDB: MDB00000090)

Physical Properties

Predicted Properties

Property	Value	Source
logP	-0.47	ChemAxon
pKa (Strongest Acidic)	3.78	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	18.84 m³·mol⁻¹	ChemAxon
Polarizability	8.06 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000190

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

422

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Lao, Hanzhang; Sun, Jianrong; Wang, Jian; Qian, Zhiliang. Process for preparation of high-purity L-lactic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 9pp.

Showing chemical card for L-Lactic acid (CFc000000122)

MOL for CFc000000122 (L-Lactic acid)

3D MOL for CFc000000122 (L-Lactic acid)

3D SDF for CFc000000122 (L-Lactic acid)

3D-SDF for CFc000000122 (L-Lactic acid)

PDB for CFc000000122 (L-Lactic acid)

3D PDB for CFc000000122 (L-Lactic acid)

SMILES for CFc000000122 (L-Lactic acid)

INCHI for CFc000000122 (L-Lactic acid)

Structure for CFc000000122 (L-Lactic acid)

3D Structure for CFc000000122 (L-Lactic acid)