Showing metabocard for L-Lactic acid (MMDBc0000062)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:29:00 UTC
Update Date2022-08-30 23:28:39 UTC
Metabolite IDMMDBc0000062
Metabolite Identification
Common NameL-Lactic acid
DescriptionLactic 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 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. 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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f5abd121848>


  Mrv1652309032023562D          

  6  5  0  0  0  0            999 V2000
   -0.3572    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0  0  0  0
  1  2  1  0  0  0  0
  2  6  1  6  0  0  0
  1  3  1  0  0  0  0
  4  2  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f5abd121848>

HMDB0000190
     RDKit          3D
L-Lactic acid
 12 11  0  0  0  0  0  0  0  0999 V2000
   -0.6908    1.0865    0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3127   -0.3809   -0.0884 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1468   -1.1979    0.6950 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0828   -0.5657    0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3869   -1.3562    1.2495 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0877    0.1328   -0.3010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7469    1.0917    0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0180    1.5790    0.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6320    1.6420   -0.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4553   -0.6149   -1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6856   -1.7842    0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1308    0.3678   -1.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  6
  3 11  1  0
  6 12  1  0
M  END
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3D SDF for #<Metabolite:0x00007f5abd121848>


  Mrv1652309032023562D          

  6  5  0  0  0  0            999 V2000
   -0.3572    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0  0  0  0
  1  2  1  0  0  0  0
  2  6  1  6  0  0  0
  1  3  1  0  0  0  0
  4  2  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000062

> <DATABASE_NAME>
MIME

> <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

> <FORMULA>
C3H6O3

> <MOLECULAR_WEIGHT>
90.0779

> <EXACT_MASS>
90.031694058

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
8.05675743839785

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-hydroxypropanoic acid

> <JCHEM_LOGP>
-0.47182951800000017

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.593508084825753

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.784942414122652

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6696493832413326

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
18.8398

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(α)-lactate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f5abd121848>

HMDB0000190
     RDKit          3D
L-Lactic acid
 12 11  0  0  0  0  0  0  0  0999 V2000
   -0.6908    1.0865    0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3127   -0.3809   -0.0884 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1468   -1.1979    0.6950 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0828   -0.5657    0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3869   -1.3562    1.2495 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0877    0.1328   -0.3010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7469    1.0917    0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0180    1.5790    0.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6320    1.6420   -0.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4553   -0.6149   -1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6856   -1.7842    0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1308    0.3678   -1.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  6
  3 11  1  0
  6 12  1  0
M  END
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PDB for #<Metabolite:0x00007f5abd121848>

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0      -0.667   0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.001  -0.385   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.001   0.385   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.667   1.925   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.667  -1.925   0.000  0.00  0.00           O+0
CONECT    1    5    2    3                                                  
CONECT    2    1    6    4                                                  
CONECT    3    1                                                            
CONECT    4    2                                                            
CONECT    5    1                                                            
CONECT    6    2                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for #<Metabolite:0x00007f5abd121848>

COMPND    HMDB0000190
HETATM    1  C1  UNL     1      -0.691   1.086   0.094  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.313  -0.381  -0.088  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.147  -1.198   0.695  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.083  -0.566   0.325  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.387  -1.356   1.250  1.00  0.00           O  
HETATM    6  O3  UNL     1       2.088   0.133  -0.301  1.00  0.00           O  
HETATM    7  H1  UNL     1      -1.747   1.092   0.408  1.00  0.00           H  
HETATM    8  H2  UNL     1      -0.018   1.579   0.805  1.00  0.00           H  
HETATM    9  H3  UNL     1      -0.632   1.642  -0.866  1.00  0.00           H  
HETATM   10  H4  UNL     1      -0.455  -0.615  -1.157  1.00  0.00           H  
HETATM   11  H5  UNL     1      -1.686  -1.784   0.108  1.00  0.00           H  
HETATM   12  H6  UNL     1       2.131   0.368  -1.273  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3    4   10
CONECT    3   11
CONECT    4    5    5    6
CONECT    6   12
END
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SMILES for #<Metabolite:0x00007f5abd121848>

C[C@H](O)C(O)=O
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INCHI for #<Metabolite:0x00007f5abd121848>

InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1
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Synonyms
ValueSource
(+)-Lactic acidChEBI
(S)-(+)-Lactic acidChEBI
(S)-2-Hydroxypropanoic acidChEBI
(S)-2-Hydroxypropionic acidChEBI
L-(+)-alpha-Hydroxypropionic acidChEBI
L-(+)-Lactic acidChEBI
L-MilchsaeureChEBI
L-LactateKegg
(+)-LactateGenerator
(S)-(+)-LactateGenerator
(S)-2-HydroxypropanoateGenerator
(S)-2-HydroxypropionateGenerator
L-(+)-a-HydroxypropionateGenerator
L-(+)-a-Hydroxypropionic acidGenerator
L-(+)-alpha-HydroxypropionateGenerator
L-(+)-Α-hydroxypropionateGenerator
L-(+)-Α-hydroxypropionic acidGenerator
L-(+)-LactateGenerator
(alpha)-LactateHMDB
(alpha)-Lactic acidHMDB
(S)-(+)-2-HydroxypropanoateHMDB
(S)-(+)-2-Hydroxypropanoic acidHMDB
(S)-2-Hydroxy-propanoateHMDB
(S)-2-Hydroxy-propanoic acidHMDB
(S)-LactateHMDB
(S)-Lactic acidHMDB
1-Hydroxyethane 1-carboxylateHMDB
1-Hydroxyethane 1-carboxylic acidHMDB
1-HydroxyethanecarboxylateHMDB
1-Hydroxyethanecarboxylic acidHMDB
2-HydroxypropanoateHMDB
2-Hydroxypropanoic acidHMDB
2-HydroxypropionateHMDB
a-HydroxypropanoateHMDB
a-Hydroxypropanoic acidHMDB
a-HydroxypropionateHMDB
a-Hydroxypropionic acidHMDB
alpha-HydroxypropanoateHMDB
alpha-Hydroxypropanoic acidHMDB
alpha-HydroxypropionateHMDB
alpha-Hydroxypropionic acidHMDB
L-(+)- Lactic acidHMDB
L-2-HydroxypropanoateHMDB
L-2-Hydroxypropanoic acidHMDB
LactateHMDB
Lactic acidHMDB
Milk acidHMDB
Sarcolactic acidHMDB
2-Hydroxypropionic acidHMDB
D-Lactic acidHMDB
D Lactic acidHMDB
Lactate, ammoniumHMDB
2 Hydroxypropanoic acidHMDB
2 Hydroxypropionic acidHMDB
Ammonium lactateHMDB
L Lactic acidHMDB
D-LactateHMDB
L-Lactic acidChEBI
Molecular FormulaC3H6O3
Average Mass90.0779
Monoisotopic Mass90.031694058
IUPAC Name(2S)-2-hydroxypropanoic acid
Traditional Name(α)-lactate
CAS Registry Number79-33-4
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 KeyJVTAAEKCZFNVCJ-REOHCLBHSA-N