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Identification
YMDB IDYMDB00247
NameL-Lactic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionLactic acid is an organic acid with two optical isomers. L-(+)-Lactic acid is the biologically important isomer. It is primarily produced by yeast and lactic acid bacteria from malic acid. It is responsible for the milky flavours in wine and the sour flavor of sourdough breads.
Structure
Thumb
Synonyms
  • (+)-Lactate
  • (+)-Lactic acid
  • (alpha)-Lactate
  • (alpha)-Lactic acid
  • (S)-(+)-2-Hydroxypropanoate
  • (S)-(+)-2-Hydroxypropanoic acid
  • (S)-(+)-Lactic acid
  • (S)-2-hydroxy-Propanoate
  • (S)-2-hydroxy-Propanoic acid
  • (S)-2-Hydroxypropanoate
  • (S)-2-Hydroxypropanoic acid
  • (S)-2-Hydroxypropionate
  • (S)-2-Hydroxypropionic acid
  • (S)-Lactate
  • (S)-Lactic acid
  • 1-Hydroxyethane 1-carboxylate
  • 1-Hydroxyethane 1-carboxylic acid
  • 1-Hydroxyethanecarboxylate
  • 1-Hydroxyethanecarboxylic acid
  • 2-Hydroxypropanoate
  • 2-Hydroxypropanoic acid
  • 2-Hydroxypropionate
  • a-Hydroxypropanoate
  • a-Hydroxypropanoic acid
  • a-Hydroxypropionate
  • a-Hydroxypropionic acid
  • alpha-Hydroxypropanoate
  • alpha-Hydroxypropanoic acid
  • alpha-Hydroxypropionate
  • alpha-Hydroxypropionic acid
  • d-Lactic acid
  • Espiritin
  • hydroxypropionic acid
  • l-(+)- lactic acid
  • L-(+)-Lactic acid
  • L-2-Hydroxypropanoate
  • L-2-Hydroxypropanoic acid
  • L-Lactate
  • l-lactic acid
  • Lactate
  • Lactic acid
  • Lactic acid, L-
  • Milk acid
  • Paralactic acid
  • Propanoic acid, 2-hydroxy-, (S)-
  • Propel
  • Sarcolactic acid
  • Tisulac
  • (-)-Lactic acid
  • (R)-(-)-Lactic acid
  • D-2-Hydroxypropanoic acid
  • D-2-Hydroxypropionic acid
  • D-Milchsaeure
  • D-Lactate
  • (-)-Lactate
  • (R)-(-)-Lactate
  • D-2-Hydroxypropanoate
  • D-2-Hydroxypropionate
  • 2-Hydroxypropionic acid
  • 2 Hydroxypropanoic acid
  • 2 Hydroxypropionic acid
  • Ammonium lactate
  • L Lactic acid
  • D Lactic acid
  • Lactate, ammonium
  • (R)-2-Hydroxypropanoate
  • (R)-2-Hydroxypropanoic acid
  • (R)-2-Hydroxypropionate
  • (R)-2-Hydroxypropionic acid
  • (R)-a-Hydroxypropionate
  • (R)-a-Hydroxypropionic acid
  • (R)-alpha-Hydroxypropionate
  • (R)-alpha-Hydroxypropionic acid
  • (R)-Lactate
  • (R)-Lactic acid
  • D-(-)-Lactate
  • D-(-)-Lactic acid
  • delta-(-)-Lactate
  • delta-(-)-Lactic acid
  • delta-2-Hydroxypropanoate
  • delta-2-Hydroxypropanoic acid
  • delta-2-Hydroxypropionate
  • delta-2-Hydroxypropionic acid
  • delta-Lactate
  • delta-Lactic acid
  • DLA
  • L-(+)-Lactate
CAS number79-33-4
WeightAverage: 90.0779
Monoisotopic: 90.031694058
InChI KeyJVTAAEKCZFNVCJ-REOHCLBHSA-N
InChIInChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1
IUPAC Name(2R)-2-hydroxypropanoic acid
Traditional IUPAC NameD-lactic acid
Chemical FormulaC3H6O3
SMILES[H]OC(=O)[C@@]([H])(O[H])C([H])([H])[H]
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
Physical Properties
StateLiquid
Charge0
Melting point16.8 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility562 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
AcidicFDB003294
OdorlessFDB003294
SMPDB Pathways
Pyruvate metabolismPW002447 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycolysis / Gluconeogenesisec00010 Map00010
Propanoate metabolismec00640 Map00640
Pyruvate metabolismec00620 Map00620
SMPDB Reactions
L-Lactic acid + NADPyruvic acid + NADH + hydron
L-Lactic acid + ferricytochrome c Pyruvic acid + Ferrocytochrome + hydron
KEGG Reactions
L-Lactic acid + ferricytochrome c → ferrocytochrome c + Pyruvic acid
NAD + water + LactaldehydeNADH + L-Lactic acid + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
533 ± 44 µM hops, malted barleyanaerobicBaker's yeastPMID: 16448171
Conversion Details Here
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Almeida, C., Duarte, I. F., Barros, A., Rodrigues, J., Spraul, M., Gil, A. M. (2006). "Composition of beer by 1H NMR spectroscopy: effects of brewing site and date of production." J Agric Food Chem 54:700-706.16448171
  • Inoue, Y., Watanabe, K., Shimosaka, M., Saikusa, T., Fukuda, Y., Murata, K., Kimura, A. (1985). "Metabolism of 2-oxoaldehydes in yeasts. Purification and characterization of lactaldehyde dehydrogenase from Saccharomyces cerevisiae." Eur J Biochem 153:243-247.3908097
  • Casal, M., Paiva, S., Andrade, R. P., Gancedo, C., Leao, C. (1999). "The lactate-proton symport of Saccharomyces cerevisiae is encoded by JEN1." J Bacteriol 181:2620-2623.10198029
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
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.
External Links:
ResourceLink
CHEBI ID422
HMDB IDHMDB00190
Pubchem Compound ID107689
Kegg IDC00186
ChemSpider ID96860
FOODB IDFDB003294
WikipediaLactic_acid
BioCyc IDL-LACTATE

Enzymes

General function:
Involved in catalytic activity
Specific function:
(S)-lactate + 2 ferricytochrome c = pyruvate + 2 ferrocytochrome c + 2 H(+)
Gene Name:
CYB2
Uniprot ID:
P00175
Molecular weight:
65538.79688
Reactions
(S)-lactate + 2 ferricytochrome c → pyruvate + 2 ferrocytochrome c + 2 H(+).
General function:
Involved in iron ion binding
Specific function:
Electron carrier protein. The oxidized form of the cytochrome c heme group can accept an electron from the heme group of the cytochrome c1 subunit of cytochrome reductase. Cytochrome c then transfers this electron to the cytochrome oxidase complex, the final protein carrier in the mitochondrial electron-transport chain
Gene Name:
CYC1
Uniprot ID:
P00044
Molecular weight:
12181.90039
Reactions
General function:
Involved in iron ion binding
Specific function:
Electron carrier protein. The oxidized form of the cytochrome c heme group can accept an electron from the heme group of the cytochrome c1 subunit of cytochrome reductase. Cytochrome c then transfers this electron to the cytochrome oxidase complex, the final protein carrier in the mitochondrial electron-transport chain
Gene Name:
CYC7
Uniprot ID:
P00045
Molecular weight:
12532.2998
Reactions

Transporters

General function:
Involved in carbohydrate transmembrane transporter activity
Specific function:
Essential to lactate transport
Gene Name:
JEN1
Uniprot ID:
P36035
Molecular weight:
69375.60156