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Showing metabocard for D-Lactic acid (HMDB0001311)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-07-18 20:19:55 UTC
HMDB IDHMDB0001311
Secondary Accession Numbers
  • HMDB0000171
  • HMDB00171
  • HMDB01311
Metabolite Identification
Common NameD-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. D-Lactic acid is the end product of the enzyme glyoxalase II (or hydroxyacyl-glutathione hydrolase) (EC 3.1.2.6), which converts the intermediate substrate S-lactoyl-glutathione to reduced glutathione and D-lactate (OMIM: 138790 ). Lactic acid is a microbial metabolite found in Aerococcus, Bacillus, Carnobacterium, Corynebacterium, Enterococcus, Escherichia, Lactobacillus, Lactococcus, Leuconostoc, Oenococcus, Pediococcus, Rhizopus, Saccharomyces, Streptococcus, Tetragenococcus, Vagococcus and Weissella (PMID:26287368 ; PMID:26360870 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001311 (D-Lactic acid)

  Mrv1652305271900072D          

  6  5  0  0  0  0            999 V2000
10025.873410025.3234    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10025.156310025.7356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10024.441910025.3234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10025.156310026.5606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10026.587010025.7356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10025.873410024.4984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  6  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
M  END
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3D MOL for HMDB0001311 (D-Lactic acid)

HMDB0001311
     RDKit          3D
D-Lactic acid
 12 11  0  0  0  0  0  0  0  0999 V2000
   -1.3335   -0.3512    0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0692    0.1042   -0.3514 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1463    1.4259    0.0256 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0978   -0.7004   -0.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1677   -1.9332   -0.2436 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893   -0.1036    0.5961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8058   -1.2071   -0.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0364    0.5312    0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1556   -0.5189    1.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2845    0.0560   -1.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5941    1.9949   -0.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6780    0.7021    0.1752 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 HMDB0001311 (D-Lactic acid)

  Mrv1652305271900072D          

  6  5  0  0  0  0            999 V2000
10025.873410025.3234    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10025.156310025.7356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10024.441910025.3234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10025.156310026.5606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10026.587010025.7356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10025.873410024.4984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  6  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001311

> <DATABASE_NAME>
hmdb

> <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-/m1/s1

> <INCHI_KEY>
JVTAAEKCZFNVCJ-UWTATZPHSA-N

> <FORMULA>
C3H6O3

> <MOLECULAR_WEIGHT>
90.0779

> <EXACT_MASS>
90.031694058

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
8.053681838559413

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.79

> <JCHEM_LOGP>
-0.47182951800000017

> <ALOGPS_LOGS>
0.79

> <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>
18.839800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.62e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
D-lactic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001311 (D-Lactic acid)

HMDB0001311
     RDKit          3D
D-Lactic acid
 12 11  0  0  0  0  0  0  0  0999 V2000
   -1.3335   -0.3512    0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0692    0.1042   -0.3514 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1463    1.4259    0.0256 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0978   -0.7004   -0.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1677   -1.9332   -0.2436 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893   -0.1036    0.5961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8058   -1.2071   -0.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0364    0.5312    0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1556   -0.5189    1.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2845    0.0560   -1.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5941    1.9949   -0.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6780    0.7021    0.1752 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 HMDB0001311 (D-Lactic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8714.9648713.937   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8713.6258714.706   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8712.2928713.937   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8713.6258716.246   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8716.2968714.706   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8714.9648712.397   0.000  0.00  0.00           O+0
CONECT    1    2    5    6                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    1                                                            
CONECT    6    1                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for HMDB0001311 (D-Lactic acid)

COMPND    HMDB0001311
HETATM    1  C1  UNL     1      -1.334  -0.351   0.344  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.069   0.104  -0.351  1.00  0.00           C  
HETATM    3  O1  UNL     1       0.146   1.426   0.026  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.098  -0.700  -0.011  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.168  -1.933  -0.244  1.00  0.00           O  
HETATM    6  O3  UNL     1       2.189  -0.104   0.596  1.00  0.00           O  
HETATM    7  H1  UNL     1      -1.806  -1.207  -0.164  1.00  0.00           H  
HETATM    8  H2  UNL     1      -2.036   0.531   0.299  1.00  0.00           H  
HETATM    9  H3  UNL     1      -1.156  -0.519   1.425  1.00  0.00           H  
HETATM   10  H4  UNL     1      -0.285   0.056  -1.446  1.00  0.00           H  
HETATM   11  H5  UNL     1      -0.594   1.995  -0.315  1.00  0.00           H  
HETATM   12  H6  UNL     1       2.678   0.702   0.175  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 HMDB0001311 (D-Lactic acid)

C[C@@H](O)C(O)=O
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INCHI for HMDB0001311 (D-Lactic acid)

InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m1/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC3H6O3
Average Molecular Weight90.0779
Monoisotopic Molecular Weight90.031694058
IUPAC Name(2R)-2-hydroxypropanoic acid
Traditional NameD-lactic acid
CAS Registry Number10326-41-7
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-/m1/s1
InChI KeyJVTAAEKCZFNVCJ-UWTATZPHSA-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassAlpha hydroxy acids and derivatives
Direct ParentAlpha 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effectOrganoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Indirect biological roleBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point52.8 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Liver
  • Neuron
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified11.0 +/- 1.2 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified7.26 +/- 0.481 uMAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified8 +/- 4.6 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified508+/-293 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
 details
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 2
  1. McLellan AC, Phillips SA, Thornalley PJ: Fluorimetric assay of D-lactate. Anal Biochem. 1992 Oct;206(1):12-6. [PubMed:1456422 ]
Schizophrenia
  1. Fukushima T, Iizuka H, Yokota A, Suzuki T, Ohno C, Kono Y, Nishikiori M, Seki A, Ichiba H, Watanabe Y, Hongo S, Utsunomiya M, Nakatani M, Sadamoto K, Yoshio T: Quantitative analyses of schizophrenia-associated metabolites in serum: serum D-lactate levels are negatively correlated with gamma-glutamylcysteine in medicated schizophrenia patients. PLoS One. 2014 Jul 8;9(7):e101652. doi: 10.1371/journal.pone.0101652. eCollection 2014. [PubMed:25004141 ]
D-Lactic Acidosis
  1. Duran M, Van Biervliet JP, Kamerling JP, Wadman SK: D-lactic aciduria, an inborn error of metabolism? Clin Chim Acta. 1977 Feb 1;74(3):297-300. [PubMed:832430 ]
Sepsis
  1. Fan SL, Miller NS, Lee J, Remick DG: Diagnosing sepsis - The role of laboratory medicine. Clin Chim Acta. 2016 Sep 1;460:203-10. doi: 10.1016/j.cca.2016.07.002. Epub 2016 Jul 4. [PubMed:27387712 ]
D-Lactic Acidosis and Short Bowel Syndrome
  1. Uribarri J, Oh MS, Carroll HJ: D-lactic acidosis. A review of clinical presentation, biochemical features, and pathophysiologic mechanisms. Medicine (Baltimore). 1998 Mar;77(2):73-82. [PubMed:9556700 ]
Associated OMIM IDs
DrugBank IDDB03066
Phenol Explorer Compound IDNot Available
FooDB IDFDB030146
KNApSAcK IDC00019549
Chemspider ID55423
KEGG Compound IDC00256
BioCyc IDD-LACTATE
BiGG ID34414
Wikipedia LinkLactic_acid
METLIN ID6150
PubChem Compound61503
PDB IDNot Available
ChEBI ID42111
Food Biomarker OntologyNot Available
VMH IDLAC_D
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceHsieh, 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.
Material Safety Data Sheet (MSDS)Not Available
General References

Enzymes

Enzyme Details
1. Hydroxyacylglutathione hydrolase, mitochondrial
General function:
Involved in hydrolase activity
Specific function:
Thiolesterase that catalyzes the hydrolysis of S-D-lactoyl-glutathione to form glutathione and D-lactic acid.
Gene Name:
HAGH
Uniprot ID:
Q16775
Molecular weight:
28859.855
Reactions
S-Lactoylglutathione + Water → Glutathione + D-Lactic aciddetails
Enzyme Details
2. Probable D-lactate dehydrogenase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
LDHD
Uniprot ID:
Q86WU2
Molecular weight:
54870.18
Reactions
D-Lactic acid + ferricytochrome c → Pyruvic acid + ferrocytochrome c + Hydrogen Iondetails
D-Lactic acid + Ferricytochrome c → Pyruvic acid + Ferrocytochrome c + Hydrogen Iondetails
Enzyme Details
3. Hydroxyacylglutathione hydrolase-like protein
General function:
Involved in hydrolase activity
Specific function:
Hydrolase acting on ester bonds (Potential).
Gene Name:
HAGHL
Uniprot ID:
Q6PII5
Molecular weight:
Not Available
Reactions
S-Lactoylglutathione + Water → Glutathione + D-Lactic aciddetails

Transporters

Enzyme Details
1. Monocarboxylate transporter 4
General function:
Involved in transmembrane transport
Specific function:
Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
Gene Name:
SLC16A3
Uniprot ID:
O15427
Molecular weight:
49468.9
References
  1. Manning Fox JE, Meredith D, Halestrap AP: Characterisation of human monocarboxylate transporter 4 substantiates its role in lactic acid efflux from skeletal muscle. J Physiol. 2000 Dec 1;529 Pt 2:285-93. [PubMed:11101640 ]
Enzyme Details
2. Monocarboxylate transporter 1
General function:
Involved in transmembrane transport
Specific function:
Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
Gene Name:
SLC16A1
Uniprot ID:
P53985
Molecular weight:
53957.7
References
  1. Lin RY, Vera JC, Chaganti RS, Golde DW: Human monocarboxylate transporter 2 (MCT2) is a high affinity pyruvate transporter. J Biol Chem. 1998 Oct 30;273(44):28959-65. [PubMed:9786900 ]
  2. Tamai I, Sai Y, Ono A, Kido Y, Yabuuchi H, Takanaga H, Satoh E, Ogihara T, Amano O, Izeki S, Tsuji A: Immunohistochemical and functional characterization of pH-dependent intestinal absorption of weak organic acids by the monocarboxylic acid transporter MCT1. J Pharm Pharmacol. 1999 Oct;51(10):1113-21. [PubMed:10579682 ]
  3. Takanaga H, Tamai I, Inaba S, Sai Y, Higashida H, Yamamoto H, Tsuji A: cDNA cloning and functional characterization of rat intestinal monocarboxylate transporter. Biochem Biophys Res Commun. 1995 Dec 5;217(1):370-7. [PubMed:8526936 ]
Enzyme Details
3. Monocarboxylate transporter 2
General function:
Involved in transmembrane transport
Specific function:
Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate. MCT2 is a high affinity pyruvate transporter
Gene Name:
SLC16A7
Uniprot ID:
O60669
Molecular weight:
52185.7
References
  1. Lin RY, Vera JC, Chaganti RS, Golde DW: Human monocarboxylate transporter 2 (MCT2) is a high affinity pyruvate transporter. J Biol Chem. 1998 Oct 30;273(44):28959-65. [PubMed:9786900 ]