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Human Metabolome Database Version 3.5

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Showing metabocard for L-Lactic acid (HMDB00190)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:02 -0700
HMDB ID HMDB00190
Secondary Accession Numbers
  • HMDB03328
Metabolite Identification
Common Name L-Lactic acid
Description Lactic acid plays a role in several biochemical processes and is produced in the muscles during intense activity. Lactate measurement in the critically ill has been traditionally used to stratify patients with poor outcome. 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 such as man who are forced to produce ATP for their integrity 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 the cell 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 Link_out) A number of studies have demonstrated that malignant transformation is associated with an increase in glycolytic flux and in anaerobic and aerobic cellular lactate excretion. Using quantitative bioluminescence imaging in various primary carcinomas in patients (uterine cervix, head and neck, colorectal region) at first diagnosis of the disease, lactate concentrations in tumors in vivo could be relatively low or extremely high (up to 40 micromol/g) in different individual tumors or within the same lesion. In all tumor entities investigated, high molar concentrations of lactate were correlated with a high incidence of distant metastasis already in an early stage of the disease. Low lactate tumors (< median of approximately 8 micromol/g) were associated with both a longer overall and disease free survival compared to high lactate lesions (lactate > approximately 8 micromol/g). Lactate dehydrogenase was found to be upregulated in most of these tumors compared to surrounding normal tissue. (PMID 15279558 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (+)-Lactate
  2. (+)-Lactic acid
  3. (alpha)-Lactate
  4. (alpha)-Lactic acid
  5. (S)-(+)-2-Hydroxypropanoate
  6. (S)-(+)-2-Hydroxypropanoic acid
  7. (S)-2-hydroxy-Propanoate
  8. (S)-2-hydroxy-Propanoic acid
  9. (S)-2-Hydroxypropanoate
  10. (S)-2-Hydroxypropanoic acid
  11. (S)-2-Hydroxypropionate
  12. (S)-2-Hydroxypropionic acid
  13. (S)-Lactate
  14. (S)-Lactic acid
  15. 1-Hydroxyethane 1-carboxylate
  16. 1-Hydroxyethane 1-carboxylic acid
  17. 1-Hydroxyethanecarboxylate
  18. 1-Hydroxyethanecarboxylic acid
  19. 2-Hydroxypropanoate
  20. 2-Hydroxypropanoic acid
  21. 2-Hydroxypropionate
  22. a-Hydroxypropanoate
  23. a-Hydroxypropanoic acid
  24. a-Hydroxypropionate
  25. a-Hydroxypropionic acid
  26. alpha-Hydroxypropanoate
  27. alpha-Hydroxypropanoic acid
  28. alpha-Hydroxypropionate
  29. alpha-Hydroxypropionic acid
  30. L-(+)- Lactic acid
  31. L-2-Hydroxypropanoate
  32. L-2-Hydroxypropanoic acid
  33. Lactate
  34. Lactic acid
  35. Milk acid
  36. Sarcolactic acid
Chemical Formula C3H6O3
Average Molecular Weight 90.0779
Monoisotopic Molecular Weight 90.031694058
IUPAC Name (2S)-2-hydroxypropanoic acid
Traditional IUPAC Name (+)-lactic acid
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
Kingdom Organic Compounds
Super Class Organic Acids and Derivatives
Class Hydroxy Acids and Derivatives
Sub Class Alpha Hydroxy Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • lactic acid(ChEBI)
Substituents
  • Carboxylic Acid
  • Secondary Alcohol
Direct Parent Alpha Hydroxy Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Cysteine metabolism
  • Component of Propanoate metabolism
  • Component of Pyruvate metabolism
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point 16.8 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 562 g/L ALOGPS
LogP -0.79 ALOGPS
LogP -0.47 ChemAxon
LogS 0.79 ALOGPS
pKa (strongest acidic) 3.78 ChemAxon
pKa (strongest basic) -3.7 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 57.53 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 18.84 ChemAxon
Polarizability 8.06 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
13C NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Bile
  • Blood
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • All Tissues
Pathways
Name SMPDB Link KEGG Link
Gluconeogenesis SMP00128 map00010 Link_out
Pyruvate Metabolism SMP00060 map00620 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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740.0 +/- 2400.0 uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
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2390.0 +/- 990.0 uM Newborn (0-30 days old) Both Normal Not Available
Blood Detected and Quantified
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1140.0 +/- 360.0 uM Children (1-13 year old) Both Normal Not Available
Blood Detected and Quantified
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1510.0 (740.0-2400.0) uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
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2976.0 +/- 1555.0 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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6400.0 +/- 2000.0 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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1236.0 (367.0-3245.0) uM Newborn (0-30 days old) Both Normal Not Available
Blood Detected and Quantified
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1489.4 +/- 371.2 uM Adult (>18 years old) Not Specified Normal Not Available
Cellular Cytoplasm Detected and Quantified
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3200 (2900-3500) uM Adult (>18 years old) Both Normal Not Available
Cellular Cytoplasm Detected and Quantified
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1100 (600-1600) uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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1651 +/- 626 uM Not Specified Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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1590.0 +/- 330.0 uM Children (1-13 year old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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850.0 +/- 400.0 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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2240.0 +/- 600.0 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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850.0 (450.0-2100.0) uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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3000.0 (1850.0-4150.0) uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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1770.0 (930.0-2600.0) uM Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Male Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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50.73 +/- 53.54 umol/mmol creatinine Infant (0-1 year old) Both Normal Not Available
Urine Detected and Quantified
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13 (0-78) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
50.73 +/- 53.54 umol/mmol creatinine Infant (0-1 year old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Urine compound detected by GC-MS
Urine Detected and Quantified
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33.32-444.29 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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33.4 +/- 19.27 umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Urine Detected and Quantified
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33.7 +/- 12.37 umol/mmol creatinine Adult (>18 years old) Female Normal Not Available
Urine Detected and Quantified
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65.6 +/- 30.5 umol/mmol creatinine Newborn (0-30 days old) Both Normal Not Available
Urine Detected and Quantified
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17.0 +/- 10.2 umol/mmol creatinine Children (1-13 year old) Both Normal Not Available
Urine Detected and Quantified
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30.9 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.0015 - 0.0134 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
15.18 umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Urine Detected and Quantified
Article_icon
11.6 (3.5-29.3) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and Quantified
Article_icon
33.2 +/- 11.4 umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Urine Detected and Quantified
Article_icon
25 (13-46) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
43.2 +/- 15.1 umol/mmol creatinine Adult (>18 years old) Female Normal Not Available
Urine Detected and Quantified
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12.3 +/- 6.2 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
65.78 (21.37 – 249.66) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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17.2 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
7.1 (0.9-16.4) umol/mmol creatinine Adult (>18 years old) Both Normal by GC-MS
Urine Detected and Quantified
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70.4 (27.3-268.3) umol/mmol creatinine Newborn (0-30 days old) Both Normal Not Available
Urine Detected and Quantified
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104.9 (40.2-325.6) umol/mmol creatinine Infant (0-1 year old) Both Normal Not Available
Urine Detected and Quantified
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18.7 (5.2-117.8) umol/mmol creatinine Children (1-13 year old) Both Normal Not Available
Urine Detected and Quantified
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15.4 (4.6-77.1) umol/mmol creatinine Adolescent (13-18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Bile Detected and Quantified
Article_icon
>10 uM Adult (>18 years old) Both Hepatic and biliary malignancies Not Available
Blood Detected and Quantified
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1401.2 +/- 692.1 uM Adult (>18 years old) Not Specified Heart Transplant Not Available
Blood Detected and Quantified
Article_icon
1350.0 (900.0-1800.0) uM Adult (>18 years old) Both Chronic progressive external ophthalmoplegia and kearns-sayre syndrom Not Available
Blood Detected and Quantified
Article_icon
4000.0 (2000.0-6000.0) uM Adult (>18 years old) Both Chronic progressive external opthalmoplegia Not Available
Blood Detected and Quantified
Article_icon
500.0 +/- 130.0 uM Adult (>18 years old) Both Insulin-dependent diabetes mellitus(IDDM) Not Available
Blood Detected and Quantified
Article_icon
3500.0 +/- 4300.0 uM Adult (>18 years old) Both Acute ethanol intoxication Not Available
Blood Detected and Quantified
Article_icon
4500.00 (3000.00-6000.00) uM Adult (>18 years old) Both Lethal infantile mitochondrial disease Not Available
Cellular Cytoplasm Detected and Quantified
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16000 (13000-19000) uM Adult (>18 years old) Both Anoxia Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
1300.0 (500.0-2100.0) uM Adult (>18 years old) Both Cytochrome-C-oxidase deficiency Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
6850.0 (1700.0-12000) uM Adult (>18 years old) Both Cytochrome-C-Oxidase deficiency Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
4577.0 (1684.0-7470.0) uM Adult (>18 years old) Both Dementia of Alzheimer type (DAT) Not Available
Urine Detected and Quantified
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12.5 (0.00-25.0) umol/mmol creatinine Adult (>18 years old) Both Cytochrome-C-oxidase deficiency Not Available
Urine Detected and Quantified
Article_icon
37550.0 (100.0-75000.0) umol/mmol creatinine Adult (>18 years old) Both Cytochrome-C-Oxidase deficiency Not Available
Urine Detected and Quantified
Article_icon
440 umol/mmol creatinine Adult (>18 years old) Both Paraquat poisoning Not Available
Urine Detected and Quantified
Article_icon
0.0015 - 0.0226 umol/mmol creatinine Adult (>18 years old) Both ADPKD Not Available
Urine Detected and Quantified
Article_icon
90.28 (23.35 – 424.10) umol/mmol creatinine Adult (>18 years old) Both Type 1 diabetes Mellitus Not Available
Associated Disorders and Diseases
Disease References
Dementia
  • Redjems-Bennani N, Jeandel C, Lefebvre E, Blain H, Vidailhet M, Gueant JL: Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients. Gerontology. 1998;44(5):300-4. Pubmed: 9693263 Link_out
    Hepatic and biliary malignancies
    • Khan SA, Cox IJ, Hamilton G, Thomas HC, Taylor-Robinson SD: In vivo and in vitro nuclear magnetic resonance spectroscopy as a tool for investigating hepatobiliary disease: a review of H and P MRS applications. Liver Int. 2005 Apr;25(2):273-81. Pubmed: 15780050 Link_out
      Paraquat poisoning
      • Bairaktari E, Katopodis K, Siamopoulos KC, Tsolas O: Paraquat-induced renal injury studied by 1H nuclear magnetic resonance spectroscopy of urine. Clin Chem. 1998 Jun;44(6 Pt 1):1256-61. Pubmed: 9625050 Link_out
        Anoxia
        • Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. Pubmed: 8579834 Link_out
          Diabetes mellitus type 1
          • Blomqvist G, Alvarsson M, Grill V, Von Heijne G, Ingvar M, Thorell JO, Stone-Elander S, Widen L, Ekberg K: Effect of acute hyperketonemia on the cerebral uptake of ketone bodies in nondiabetic subjects and IDDM patients. Am J Physiol Endocrinol Metab. 2002 Jul;283(1):E20-8. Pubmed: 12067838 Link_out
            Ethanol intoxication
            • Fulop M, Bock J, Ben-Ezra J, Antony M, Danzig J, Gage JS: Plasma lactate and 3-hydroxybutyrate levels in patients with acute ethanol intoxication. Am J Med. 1986 Feb;80(2):191-4. Pubmed: 3080879 Link_out
              Chronic progressive external ophthalmoplegia and Kearns-Sayre syndrome
                • http://www.metagene.de/program/d.prg?mp=CHRONIC%20PROGRESSIVE%20EXTERNAL%20OPHTHALMOPLEGIA%20AND%20KEARNS-SAYRE%20SYNDROM
                Cytochrome C oxidase deficiency
                  • http://www.metagene.de/program/d.prg?mp=CYTOCHROME-C-OXIDASE%20DEFICIENCY
                  Associated OMIM IDs
                  • 220110 Link_out (Cytochrome C oxidase deficiency)
                  • 167320 Link_out (Dementia)
                  • 222100 Link_out (Diabetes mellitus type 1)
                  • 530000 Link_out (Chronic progressive external ophthalmoplegia and Kearns-Sayre syndrome)
                  DrugBank ID Not Available
                  Phenol Explorer Compound ID Not Available
                  Phenol Explorer Metabolite ID Not Available
                  FoodDB ID FDB003294
                  KNApSAcK ID C00001191 Link_out
                  Chemspider ID 96860 Link_out
                  KEGG Compound ID C00186 Link_out
                  BioCyc ID L-LACTATE Link_out
                  BiGG ID 34179 Link_out
                  Wikipedia Link Lactate Link_out
                  NuGOwiki Link HMDB00190 Link_out
                  Metagene Link HMDB00190 Link_out
                  METLIN ID 5205 Link_out
                  PubChem Compound 107689 Link_out
                  PDB ID 2OP Link_out
                  ChEBI ID 422 Link_out
                  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.
                  Material Safety Data Sheet (MSDS) Download (PDF)
                  General References
                  1. Nielsen J, Ytrebo LM, Borud O: Lactate and pyruvate concentrations in capillary blood from newborns. Acta Paediatr. 1994 Sep;83(9):920-2. Pubmed: 7819686 Link_out
                  2. Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. Pubmed: 15627241 Link_out
                  3. Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. Pubmed: 8579834 Link_out
                  4. Nicholson JK, Buckingham MJ, Sadler PJ: High resolution 1H n.m.r. studies of vertebrate blood and plasma. Biochem J. 1983 Jun 1;211(3):605-15. Pubmed: 6411064 Link_out
                  5. Redjems-Bennani N, Jeandel C, Lefebvre E, Blain H, Vidailhet M, Gueant JL: Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients. Gerontology. 1998;44(5):300-4. Pubmed: 9693263 Link_out
                  6. Bairaktari E, Katopodis K, Siamopoulos KC, Tsolas O: Paraquat-induced renal injury studied by 1H nuclear magnetic resonance spectroscopy of urine. Clin Chem. 1998 Jun;44(6 Pt 1):1256-61. Pubmed: 9625050 Link_out
                  7. Isotalo T, Talja M, Hellstrom P, Perttila I, Valimaa T, Tormala P, Tammela TL: A double-blind, randomized, placebo-controlled pilot study to investigate the effects of finasteride combined with a biodegradable self-reinforced poly L-lactic acid spiral stent in patients with urinary retention caused by bladder outlet obstruction from benign prostatic hyperplasia. BJU Int. 2001 Jul;88(1):30-4. Pubmed: 11446841 Link_out
                  8. Shirai Y, Kamimura K, Seki T, Morohashi M: L-lactic acid as a mosquito (Diptera: Culicidae) repellent on human and mouse skin. J Med Entomol. 2001 Jan;38(1):51-4. Pubmed: 11268691 Link_out
                  9. Wevers RA, Engelke U, Wendel U, de Jong JG, Gabreels FJ, Heerschap A: Standardized method for high-resolution 1H-NMR of cerebrospinal fluid. Clin Chem. 1995 May;41(5):744-51. Pubmed: 7729054 Link_out
                  10. Commodari F, Arnold DL, Sanctuary BC, Shoubridge EA: 1H NMR characterization of normal human cerebrospinal fluid and the detection of methylmalonic acid in a vitamin B12 deficient patient. NMR Biomed. 1991 Aug;4(4):192-200. Pubmed: 1931558 Link_out
                  11. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436 Link_out
                  12. Kaya M, Moriwaki Y, Ka T, Inokuchi T, Yamamoto A, Takahashi S, Tsutsumi Z, Tsuzita J, Oku Y, Yamamoto T: Plasma concentrations and urinary excretion of purine bases (uric acid, hypoxanthine, and xanthine) and oxypurinol after rigorous exercise. Metabolism. 2006 Jan;55(1):103-7. Pubmed: 16324927 Link_out
                  13. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. Pubmed: 15882454 Link_out
                  14. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. Pubmed: 8412012 Link_out
                  15. Khan SA, Cox IJ, Hamilton G, Thomas HC, Taylor-Robinson SD: In vivo and in vitro nuclear magnetic resonance spectroscopy as a tool for investigating hepatobiliary disease: a review of H and P MRS applications. Liver Int. 2005 Apr;25(2):273-81. Pubmed: 15780050 Link_out
                  Enzymes
                  Name: L-lactate dehydrogenase A-like 6A
                  Reactions:
                  • (S)-lactate + NAD+ = pyruvate + NADH + H+ [RN:R00703]
                  Gene Name: LDHAL6A
                  Uniprot ID: Q6ZMR3 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA