Record Information
Version1.0
Creation Date2016-09-30 22:43:57 UTC
Update Date2020-06-04 20:34:30 UTC
BMDB IDBMDB0001311
Secondary Accession Numbers
  • BMDB01311
Metabolite Identification
Common NameD-Lactic acid
DescriptionL-Lactic acid, also known as D-lactate or D-milchsaeure, 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. L-Lactic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. L-Lactic acid exists in all living species, ranging from bacteria to humans. L-Lactic acid participates in a number of enzymatic reactions, within cattle. In particular, L-Lactic acid can be converted into pyruvic acid; which is catalyzed by the enzyme L-lactate dehydrogenase. In addition, L-Lactic acid can be converted into L-lactic acid through the action of the enzyme monocarboxylate transporter. In cattle, L-lactic acid is involved in the metabolic pathway called cancer (via the Warburg effect). L-Lactic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
(-)-Lactic acidChEBI
(R)-(-)-Lactic acidChEBI
D-2-Hydroxypropanoic acidChEBI
D-2-Hydroxypropionic acidChEBI
D-MilchsaeureChEBI
LACTIC ACIDChEBI
D-LactateKegg
(-)-LactateGenerator
(R)-(-)-LactateGenerator
D-2-HydroxypropanoateGenerator
D-2-HydroxypropionateGenerator
LACTateGenerator
L-LactateHMDB
(R)-2-HydroxypropanoateHMDB
(R)-2-Hydroxypropanoic acidHMDB
(R)-2-HydroxypropionateHMDB
(R)-2-Hydroxypropionic acidHMDB
(R)-a-HydroxypropionateHMDB
(R)-a-Hydroxypropionic acidHMDB
(R)-alpha-HydroxypropionateHMDB
(R)-alpha-Hydroxypropionic acidHMDB
(R)-LactateHMDB
(R)-Lactic acidHMDB
D-(-)-LactateHMDB
D-(-)-Lactic acidHMDB
delta-(-)-LactateHMDB
delta-(-)-Lactic acidHMDB
delta-2-HydroxypropanoateHMDB
delta-2-Hydroxypropanoic acidHMDB
delta-2-HydroxypropionateHMDB
delta-2-Hydroxypropionic acidHMDB
delta-LactateHMDB
delta-Lactic acidHMDB
DLAHMDB
L-(+)-LactateHMDB
PropelHMDB
TisulacHMDB
2 Hydroxypropanoic acidHMDB
2 Hydroxypropionic acidHMDB
2-Hydroxypropanoic acidHMDB
Ammonium lactateHMDB
L Lactic acidHMDB
2-Hydroxypropionic acidHMDB
Sarcolactic acidHMDB
D Lactic acidHMDB
Lactate, ammoniumHMDB
L-Lactic acidHMDB
D-Lactic acidChEBI
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
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point52.8 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.79ALOGPS
logP-0.47ChemAxon
logS0.79ALOGPS
pKa (Strongest Acidic)3.78ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity18.84 m³·mol⁻¹ChemAxon
Polarizability8.05 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Liver
  • Mammary Gland
  • Neuron
  • Placenta
  • Platelet
  • Ruminal Fluid
  • Semen
  • Skeletal Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BladderExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified3560 +/- 270 uMAdultBothNormal details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001311
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
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 ReferencesNot Available