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Human Metabolome Database Version 2.5

 

Showing metabocard for D-Lactic acid (HMDB01311)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2010-04-16 16:19:13
Accession Number HMDB01311
Secondary Accession Numbers HMDB00171
Common Name D-Lactic acid
Description D-Lactic acid is the end product of the enzyme Glyoxalase II ([EC:3.1.2.6] hydroxyacyl-glutathione hydrolase) which converts the intermediate substrate S-lactoyl-glutathione to reduced glutathione and D-lactate. (OMIM 138790)
Synonyms
  1. (-)-Lactate
  2. (-)-Lactic acid
  3. (R)-(-)-Lactate
  4. (R)-(-)-Lactic acid
  5. (R)-2-Hydroxypropanoate
  6. (R)-2-Hydroxypropanoic acid
  7. (R)-2-Hydroxypropionate
  8. (R)-2-Hydroxypropionic acid
  9. (R)-Lactate
  10. (R)-Lactic acid
  11. (R)-a-Hydroxypropionate
  12. (R)-a-Hydroxypropionic acid
  13. (R)-alpha-Hydroxypropionate
  14. (R)-alpha-Hydroxypropionic acid
  15. D-(-)-Lactate
  16. D-(-)-Lactic acid
  17. D-2-Hydroxypropanoate
  18. D-2-Hydroxypropanoic acid
  19. D-2-Hydroxypropionate
  20. D-2-Hydroxypropionic acid
  21. D-Lactate
  22. D-Lactic acid
  23. DLA
  24. L-(+)-Lactate
  25. L-Lactic acid
  26. Propel
  27. Tisulac
  28. delta-(-)-Lactate
  29. delta-(-)-Lactic acid
  30. delta-2-Hydroxypropanoate
  31. delta-2-Hydroxypropanoic acid
  32. delta-2-Hydroxypropionate
  33. delta-2-Hydroxypropionic acid
  34. delta-Lactate
  35. delta-Lactic acid
Chemical IUPAC Name (2R)-2-hydroxypropanoic acid
Chemical Formula C3H6O3
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Hydroxy Acids
Sub Class
  • Short chain hydroxy acids
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • carboxylic acid
  • alpha-hydroxyacid
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 90.078
Monoisotopic Molecular Weight 90.031693
Isomeric SMILES C[C@@H](O)C(O)=O
Canonical SMILES CC(O)C(O)=O
KEGG Compound ID C00256 Link Image
BioCyc ID D-LACTATE Link Image
BiGG ID 34414 Link Image
Wikipedia Link DLA Link Image
NuGOwiki Link HMDB01311 Link Image
Metagene Link HMDB01311 Link Image
METLIN ID 6150 Link Image
PubChem Compound 61503 Link Image
PubChem Substance 8187556 Link Image
ChEBI ID 341 Link Image
CAS Registry Number 10326-41-7
InChI Identifier InChI=1/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m1/s1
Synthesis Reference Hsieh, Chun Lung; Houng, Jer Yiing. Preparation of D-lactic acid from D,L-lactic acid ester using wheat germ or pancreatic lipase. U.S. (1997), 5 pp.
Melting Point (Experimental) 52.8 C
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 1000.0 mg/mL [MEYLAN,WM et al. (1996)]; 562.0 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -0.79 [Predicted by ALOGPS]; -0.6 [Predicted by PubChem via XLOGP]; -0.65 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
Show Experimental Conditions Link Image
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
Show Experimental Conditions Link Image
Simplified TOCSY Spectrum Show Image
Show Peaklist
BMRB Spectrum Show Image
Show Peaklist
Cellular Location
  • Cytoplasm (Predicted from LogP)
  • Extracellular
  • mitochondria
Biofluid Location
  • Blood
  • Urine
Tissue Location
Tissue References
Bladder —
Brain —
Fibroblasts —
Gut —
Intestine —
Liver —
Muscle —
Neuron —
Placenta —
Platelet —
Skeletal Muscle —
Skin —
Spleen —
Stratum Corneum —
Testes —
Concentrations (Normal)
Biofluid Blood
Value 11.0 +/- 1.2 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • McLellan AC, Phillips SA, Thornalley PJ: Fluorimetric assay of D-lactate. Anal Biochem. 1992 Oct;206(1):12-6. [PubMed Link Image]
Biofluid Urine
Value 23.00 uM
Age Adult:>18 yrs old
Sex Male
Patient information Normal
Comments Not Available
References
  • Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
Concentrations (Abnormal)
Biofluid Blood
Value 20.0 +/- 1.3 uM
Age Adult:>18 yrs old
Sex Both
Condition Diabetes mellitus type 2
Comments Not Available
References
  • McLellan AC, Phillips SA, Thornalley PJ: Fluorimetric assay of D-lactate. Anal Biochem. 1992 Oct;206(1):12-6. [PubMed Link Image]
Associated Disorders
Condition References
Diabetes mellitus type 2
  • McLellan AC, Phillips SA, Thornalley PJ: Fluorimetric assay of D-lactate. Anal Biochem. 1992 Oct;206(1):12-6. [PubMed Link Image]
OMIM ID
Pathways
Name SMPDB Link KEGG Link
Pyruvaldehyde Degradation SMP00459 Link Image
Pyruvate Metabolism SMP00060 Link Image map00620 Link Image
General References
  1. Hasegawa H, Fukushima T, Lee JA, Tsukamoto K, Moriya K, Ono Y, Imai K: Determination of serum D-lactic and L-lactic acids in normal subjects and diabetic patients by column-switching HPLC with pre-column fluorescence derivatization. Anal Bioanal Chem. 2003 Nov;377(5):886-91. Epub 2003 Jul 19. [PubMed Link Image]
  2. Smith SM, Eng RH, Buccini F: Use of D-lactic acid measurements in the diagnosis of bacterial infections. J Infect Dis. 1986 Oct;154(4):658-64. [PubMed Link Image]
  3. Ellis LC, Groesbeck MD, Farr CH, Tesi RJ: Contractility of seminiferous tubules as related to sperm transport in the male. Arch Androl. 1981 Jun;6(4):283-94. [PubMed Link Image]
  4. Pedersen M: Ciliary activity and pollution. Lung. 1990;168 Suppl:368-76. [PubMed Link Image]
  5. McLellan AC, Phillips SA, Thornalley PJ: Fluorimetric assay of D-lactate. Anal Biochem. 1992 Oct;206(1):12-6. [PubMed Link Image]
  6. Schmid-Schonbein GW: Microlymphatics and lymph flow. Physiol Rev. 1990 Oct;70(4):987-1028. [PubMed Link Image]
  7. Solito R, Alessandrini C, Fruschelli M, Pucci AM, Gerli R: An immunological correlation between the anchoring filaments of initial lymph vessels and the neighboring elastic fibers: a unified morphofunctional concept. Lymphology. 1997 Dec;30(4):194-202. [PubMed Link Image]
  8. Brandt RB, Siegel SA: Methylglyoxal production in human blood. Ciba Found Symp. 1978;(67):211-23. [PubMed Link Image]
  9. Zhang YJ, O'Neal WK, Randell SH, Blackburn K, Moyer MB, Boucher RC, Ostrowski LE: Identification of dynein heavy chain 7 as an inner arm component of human cilia that is synthesized but not assembled in a case of primary ciliary dyskinesia. J Biol Chem. 2002 May 17;277(20):17906-15. Epub 2002 Mar 4. [PubMed Link Image]
  10. Tanyel FC, Ulusu NN, Tezcan EF, Buyukpamukcu N: Total calcium content of sacs associated with inguinal hernia, hydrocele or undescended testis reflects differences dictated by programmed cell death. Urol Int. 2003;70(3):211-5. [PubMed Link Image]
  11. Kaneko T, Bando Y, Kurihara H, Satomi K, Nonoyama K, Matsuura N: Fecal microflora in a patient with short-bowel syndrome and identification of dominant lactobacilli. J Clin Microbiol. 1997 Dec;35(12):3181-5. [PubMed Link Image]
  12. Hoijer MA, Melief MJ, van Helden-Meeuwsen CG, Eulderink F, Hazenberg MP: Detection of muramic acid in a carbohydrate fraction of human spleen. Infect Immun. 1995 May;63(5):1652-7. [PubMed Link Image]
  13. Wikipedia Link Image
Metabolic Enzymes
  1. Hydroxyacylglutathione hydrolase
  2. Probable D-lactate dehydrogenase, mitochondrial precursor
  3. Hydroxyacylglutathione hydrolase-like protein
Enzyme 1 [top]
Enzyme 1 ID 6092
Enzyme 1 Name Hydroxyacylglutathione hydrolase
Enzyme 1 Synonyms
  1. Glyoxalase II
  2. GLX II
Enzyme 1 Gene Name HAGH
Enzyme 1 Protein Sequence >Hydroxyacylglutathione hydrolase 
MKVEVLPALTDNYMYLVIDDETKEAAIVDPVQPQKVVDAARKHGVKLTTVLTTHHHWDHA
GGNEKLVKLESGLKVYGGDDRIGALTHKITHLSTLQVGSLNVKCLATPCHTSGHICYFVS
KPGGSEPPAVFTGDTLFVAGCGKFYEGTADEMCKALLEVLGRLPPDTRVYCGHEYTINNL
KFARHVEPGNAAIREKLAWAKEKYSIGEPTVPSTLAEEFTYNPFMRVREKTVQQHAGETD
PVTTMRAVRREKDQFKMPRD
Enzyme 1 Number of Residues 260
Enzyme 1 Molecular Weight 28860
Enzyme 1 Theoretical pI 7.36
Enzyme 1 GO Classification Not Available
Enzyme 1 General Function Not Available
Enzyme 1 Specific Function Thiolesterase that catalyzes the hydrolysis of S-D- lactoyl-glutathione to form glutathione and D-lactic acid
Enzyme 1 Pathways
Enzyme 1 Reactions
  • S-(2-hydroxyacyl)glutathione + H2O = glutathione + a 2-hydroxy carboxylate
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 1237213 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q16775 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name GLO2_HUMAN Link Image
Enzyme 1 PDB ID 1QH3 Link Image
Enzyme 1 PDB File Show
Enzyme 1 3D Structure
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >783 bp 
ATGAAGGTAGAGGTGCTGCCTGCCCTGACCGACAACTACATGTACCTGGTCATTGATGAT
GAGACCAAGGAGGCTGCCATTGTGGATCCGGTGCAGCCCCAGAAGGTCGTGGACGCGGCG
AGAAAGCACGGGGTGAAACTGACCACAGTGCTCACCACCCACCACCACTGGGACCATGCT
GGCGGGAATGAGAAACTGGTCAAGCTGGAGTCGGGACTGAAGGTGTACGGGGGTGACGAC
CGTATCGGGGCCCTGACTCACAAGATCACTCACCTGTCCACACTGCAGGTGGGGTCTCTG
AACGTCAAGTGCCTGGCGACCCCGTGCCACACTTCAGGACACATTTGTTACTTCGTGAGC
AAGCCCGGAGGCTCGGAGCCCCCTGCCGTGTTCACAGGTGACACCTTGTTTGTGGCTGGC
TGCGGGAAGTTCTATGAAGGGACTGCGGATGAGATGTGTAAAGCTCTGCTGGAGGTCTTG
GGCCGGCTCCCCCCGGACACAAGAGTCTACTGTGGCCACGAGTACACCATCAACAACCTC
AAGTTTGCACGCCACGTGGAGCCCGGCAATGCCGCCATCCGGGAGAAGCTGGCCTGGGCC
AAGGAGAAGTACAGCATCGGGGAGCCCACAGTGCCATCCACCCTGGCAGAGGAGTTTACC
TACAACCCCTTCATGAGAGTGAGGGAGAAGACGGTGCAGCAGCACGCAGGTGAGACGGAC
CCGGTGACCACCATGCGGGCCGTGCGCAGGGAGAAGGACCAGTTCAAGATGCCCCGGGAC
TGA
Enzyme 1 GenBank Gene ID X90999 Link Image
Enzyme 1 GeneCard ID HAGH Link Image
Enzyme 1 GenAtlas ID HAGH Link Image
Enzyme 1 HGNC ID HGNC:4805 Link Image
Enzyme 1 Chromosome Location 16
Enzyme 1 Locus 16p13.3
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Ridderstrom M, Saccucci F, Hellman U, Bergman T, Principato G, Mannervik B: Molecular cloning, heterologous expression, and characterization of human glyoxalase II. J Biol Chem. 1996 Jan 5;271(1):319-23. [PubMed Link Image]
  2. Daniels RJ, Peden JF, Lloyd C, Horsley SW, Clark K, Tufarelli C, Kearney L, Buckle VJ, Doggett NA, Flint J, Higgs DR: Sequence, structure and pathology of the fully annotated terminal 2 Mb of the short arm of human chromosome 16. Hum Mol Genet. 2001 Feb 15;10(4):339-52. [PubMed Link Image]
  3. Cameron AD, Ridderstrom M, Olin B, Mannervik B: Crystal structure of human glyoxalase II and its complex with a glutathione thiolester substrate analogue. Structure. 1999 Sep 15;7(9):1067-78. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available
Enzyme 2 [top]
Enzyme 2 ID 9170
Enzyme 2 Name Probable D-lactate dehydrogenase, mitochondrial precursor
Enzyme 2 Synonyms
  1. Lactate dehydrogenase D
  2. DLD
Enzyme 2 Gene Name LDHD
Enzyme 2 Protein Sequence >Probable D-lactate dehydrogenase, mitochondrial precursor 
MARLLRSATWELFPWRGYCSQKAKGELCRDFVEALKAVVGGSHVSTAAVVREQHGRDESV
HRCEPPDAVVWPQNVEQVSRLAALCYRQGVPIIPFGTGTGLEGGVCAVQGGVCVNLTHMD
RILELNQEDFSVVVEPGVTRKALNAHLRDSGLWFPVDPGADASLCGMAATGASGTNAVRY
GTMRDNVLNLEVVLPDGRLLHTAGRGRHFRFGFWPEIPHHTAWYSPCVSLGRRKSAAGYN
LTGLFVGSEGTLGLITATTLRLHPAPEATVAATCAFPSVQAAVDSTVHILQAAVPVARIE
FLDEVMMDACNRYSKLNCLVAPTLFLEFHGSQQALEEQLQRTEEIVQQNGASDFSWAKEA
EERSRLWTARHNAWYAALATRPGCKGYSTDVCVPISRLPEIVVQTKEDLNASGLTGSIVG
HVGDGNFHCILLVNPDDAEELGRVKAFAEQLGRRALALHGTCTGEHGIGMGKRQLLQEEV
GAVGVETMRQLKAVLDPQGLMNPGKVL
Enzyme 2 Number of Residues 507
Enzyme 2 Molecular Weight 54871
Enzyme 2 Theoretical pI Not Available
Enzyme 2 GO Classification
Function
—
Process
  • cellular metabolism
  • electron transport
  • generation of precursor metabolites and energy
  • metabolism
  • physiological process
Component
—
Enzyme 2 General Function Energy production and conversion
Enzyme 2 Specific Function (R)-lactate + 2 ferricytochrome c = pyruvate + 2 ferrocytochrome c
Enzyme 2 Pathways
Enzyme 2 Reactions
  • Glyoxylate + H2O + Nicotinamide adenine dinucleotide --> (2)H+ + Nicotinamide adenine dinucleotide - reduced + Oxalate
Enzyme 2 Pfam Domain Function
Enzyme 2 Signals
  • None
Enzyme 2 Transmembrane Regions
  • None
Enzyme 2 Essentiality Not Available
Enzyme 2 GenBank ID Protein 23506788 Link Image
Enzyme 2 UniProtKB/Swiss-Prot ID Q86WU2 Link Image
Enzyme 2 UniProtKB/Swiss-Prot Entry Name LDHD_HUMAN Link Image
Enzyme 2 PDB ID Not Available
Enzyme 2 Cellular Location Not Available
Enzyme 2 Gene Sequence Not Available
Enzyme 2 GenBank Gene ID AY092767 Link Image
Enzyme 2 GeneCard ID Not Available
Enzyme 2 GenAtlas ID LDHD Link Image
Enzyme 2 HGNC ID HGNC:19708 Link Image
Enzyme 2 Chromosome Location Not Available
Enzyme 2 Locus Not Available
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 General References
  1. Flick MJ, Konieczny SF: Identification of putative mammalian D-lactate dehydrogenase enzymes. Biochem Biophys Res Commun. 2002 Jul 26;295(4):910-6. [PubMed Link Image]
Enzyme 2 Metabolite References Not Available
Enzyme 3 [top]
Enzyme 3 ID 11578
Enzyme 3 Name Hydroxyacylglutathione hydrolase-like protein
Enzyme 3 Synonyms Not Available
Enzyme 3 Gene Name HAGHL
Enzyme 3 Protein Sequence >Hydroxyacylglutathione hydrolase-like protein 
MKVKVIPVLEDNYMYLVIEELTREAVAVDVAVPKRLLEIVGREGVSLTAVLTTHHHWDHA
RGNPELARLRPGLAVLGADERIFSLTRRLAHGEELRFGAIHVRCLLTPGHTAGHMSYFLW
EDDCPDPPALFSGDALSVAGCGSCLEGSAQQMYQSLAELGTLPPETKVFCGHEHTLSNLE
FAQKVEPCNDHVRAKLSWAKARPLSRRGKRVGGEGTGFGVGGALRQGLMVTGACGHSRRG
MRMTCPLCRRLWARSASTTPSCGWREYGCCPGASTVTWTLRKASGDCVLG
Enzyme 3 Number of Residues 290
Enzyme 3 Molecular Weight 31558
Enzyme 3 Theoretical pI Not Available
Enzyme 3 GO Classification Not Available
Enzyme 3 General Function Not Available
Enzyme 3 Specific Function Not Available
Enzyme 3 Pathways Not Available
Enzyme 3 Reactions
  • H2O + (R)-S-Lactoylglutathione --> Reduced glutathione + H+ + D-Lactate
Enzyme 3 Pfam Domain Function
Enzyme 3 Signals
  • None
Enzyme 3 Transmembrane Regions
  • None
Enzyme 3 Essentiality Not Available
Enzyme 3 GenBank ID Protein 45708670 Link Image
Enzyme 3 UniProtKB/Swiss-Prot ID Q6PII5 Link Image
Enzyme 3 UniProtKB/Swiss-Prot Entry Name Q6PII5_HUMAN Link Image
Enzyme 3 PDB ID Not Available
Enzyme 3 Cellular Location Not Available
Enzyme 3 Gene Sequence Not Available
Enzyme 3 GenBank Gene ID BC033796 Link Image
Enzyme 3 GeneCard ID Not Available
Enzyme 3 GenAtlas ID HAGHL Link Image
Enzyme 3 HGNC ID HGNC:14177 Link Image
Enzyme 3 Chromosome Location Not Available
Enzyme 3 Locus Not Available
Enzyme 3 SNPs SNPJam Report Link Image
Enzyme 3 General References
  1. Strausberg RL, Feingold EA, Grouse LH, Derge JG, Klausner RD, Collins FS, Wagner L, Shenmen CM, Schuler GD, Altschul SF, Zeeberg B, Buetow KH, Schaefer CF, Bhat NK, Hopkins RF, Jordan H, Moore T, Max SI, Wang J, Hsieh F, Diatchenko L, Marusina K, Farmer AA, Rubin GM, Hong L, Stapleton M, Soares MB, Bonaldo MF, Casavant TL, Scheetz TE, Brownstein MJ, Usdin TB, Toshiyuki S, Carninci P, Prange C, Raha SS, Loquellano NA, Peters GJ, Abramson RD, Mullahy SJ, Bosak SA, McEwan PJ, McKernan KJ, Malek JA, Gunaratne PH, Richards S, Worley KC, Hale S, Garcia AM, Gay LJ, Hulyk SW, Villalon DK, Muzny DM, Sodergren EJ, Lu X, Gibbs RA, Fahey J, Helton E, Ketteman M, Madan A, Rodrigues S, Sanchez A, Whiting M, Madan A, Young AC, Shevchenko Y, Bouffard GG, Blakesley RW, Touchman JW, Green ED, Dickson MC, Rodriguez AC, Grimwood J, Schmutz J, Myers RM, Butterfield YS, Krzywinski MI, Skalska U, Smailus DE, Schnerch A, Schein JE, Jones SJ, Marra MA: Generation and initial analysis of more than 15,000 full-length human and mouse cDNA sequences. Proc Natl Acad Sci U S A. 2002 Dec 24;99(26):16899-903. Epub 2002 Dec 11. [PubMed Link Image]
Enzyme 3 Metabolite References Not Available