D-Lactic acid (YMDB00287)

Identification
YMDB IDYMDB00287
NameD-Lactic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionL-Lactic acid, also known as L-lactate or L-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 is an extremely weak basic (essentially neutral) compound (based on its pKa). L-Lactic acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (-)-Lactate
  • (-)-Lactic acid
  • (D)-(-)-Lactic acid
  • (R)-(-)-Lactate
  • (R)-(-)-Lactic acid
  • (R)-2-Hydroxypropanoate
  • (R)-2-Hydroxypropanoic acid
  • (R)-2-Hydroxypropionate
  • (R)-2-Hydroxypropionic acid
  • (R)-2-Hydroxypropionsaeure
  • (R)-a-Hydroxypropionate
  • (R)-a-Hydroxypropionic acid
  • (R)-alpha-Hydroxypropionate
  • (R)-alpha-Hydroxypropionic acid
  • (R)-Lactate
  • (R)-Lactic acid
  • (R)-Milchsaeure
  • 1-Lactic acid
  • D-(-)-Lactate
  • D-(-)-Lactic acid
  • D-2-Hydroxypropanoate
  • D-2-Hydroxypropanoic acid
  • D-2-Hydroxypropionate
  • D-2-Hydroxypropionic acid
  • D-Lactate
  • D-Lactic acid
  • D-Milchsaeure
  • 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
  • L-Lactic acid
  • Lactic acid (D)
  • Propanoic acid, 2-hydroxy-, (2R)-
  • Propanoic acid, 2-hydroxy-, (R)-
  • Propel
  • Tisulac
  • (+)-Lactic acid
  • (S)-(+)-Lactic acid
  • (S)-2-Hydroxypropanoic acid
  • (S)-2-Hydroxypropionic acid
  • L-(+)-alpha-Hydroxypropionic acid
  • L-(+)-Lactic acid
  • L-Milchsaeure
  • L-Lactate
  • (+)-Lactate
  • (S)-(+)-Lactate
  • (S)-2-Hydroxypropanoate
  • (S)-2-Hydroxypropionate
  • L-(+)-a-Hydroxypropionate
  • L-(+)-a-Hydroxypropionic acid
  • L-(+)-alpha-Hydroxypropionate
  • L-(+)-Α-hydroxypropionate
  • L-(+)-Α-hydroxypropionic acid
  • (alpha)-Lactate
  • (alpha)-Lactic acid
  • (S)-(+)-2-Hydroxypropanoate
  • (S)-(+)-2-Hydroxypropanoic acid
  • (S)-2-Hydroxy-propanoate
  • (S)-2-Hydroxy-propanoic 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
  • L-(+)- Lactic acid
  • L-2-Hydroxypropanoate
  • L-2-Hydroxypropanoic acid
  • Lactate
  • Lactic acid
  • Milk acid
  • Sarcolactic acid
  • 2-Hydroxypropionic acid
  • D Lactic acid
  • Lactate, ammonium
  • 2 Hydroxypropanoic acid
  • 2 Hydroxypropionic acid
  • Ammonium lactate
  • L Lactic acid
CAS number10326-41-7
WeightAverage: 90.0779
Monoisotopic: 90.031694058
InChI KeyJVTAAEKCZFNVCJ-UWTATZPHSA-N
InChIInChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m1/s1
IUPAC Name(2S)-2-hydroxypropanoic acid
Traditional IUPAC Name(α)-lactate
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
StateSolid
Charge0
Melting point52.8 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
logP-0.47ChemAxon
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
Polarizability8.06 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
AcidicFDB003294
OdorlessFDB003294
SMPDB Pathways
Pyruvate metabolismPW002447 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Pyruvate metabolismec00620 Map00620
SMPDB Reactions
S-Lactoylglutathione + water ↔ Glutathione + D-Lactic acid
D-Lactic acid + ferricytochrome c → Pyruvic acid + Pentane + hydron
KEGG Reactions
ferricytochrome c + D-Lactic acid → ferrocytochrome c + Pyruvic acid
S-Lactoylglutathione + water → Glutathione + hydron + D-Lactic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kb-0900000000-fb59ec16914501aa19abJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014j-0900000000-c4d9e12b4b0150eda54bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0900000000-fb59ec16914501aa19abJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-a3691f383d440fb00e1fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-9620000000-f7faa7db9c1be3d9d975JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-9000000000-1d5a5f55463acefb6fc7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000m-9000000000-c07133799d8f43d4c75aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-000i-9000000000-ddb080250741e69ab137JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-8f5d5eddb0b4b2a3b541JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-3bcfc4cdc49230f15642JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-48b511409f4f60cec04eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-365ea3c1bcfff2cab938JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-9d0238aeeb837213e81dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-8f5d5eddb0b4b2a3b541JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-3bcfc4cdc49230f15642JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-48b511409f4f60cec04eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-365ea3c1bcfff2cab938JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-9d0238aeeb837213e81dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-014i-9000000000-046bb7f6cce9744388ebJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000f-9000000000-1c6ea519686b2066052fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9000000000-013763552dec660fac8cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-bc4403a40640361e5a52JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-9000000000-5f417f4a6d08f0ab00edJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-9000000000-df7a94bb1a9cf6e78e1aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-9000000000-dc2a1b965287b9dfee9cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-c3686a681cc9bbf039e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-ddad20647c2ac56efd22JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-b728b45617afcc6b67daJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-b586cb8f053eb4465b4eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-400a5f1c0dfcc32ef2bbJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-002b-9000000000-50213d6b39ef9741c466JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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
  • 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
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.
External Links:
ResourceLink
CHEBI ID42111
HMDB IDHMDB01311
Pubchem Compound ID61503
Kegg IDC00256
ChemSpider ID55423
FOODB IDFDB003294
WikipediaLactic_acid
BioCyc IDD-LACTATE

Enzymes

Protein Details
1. Hydroxyacylglutathione hydrolase, cytoplasmic isozyme
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:
GLO2
Uniprot ID:
Q05584
Molecular weight:
31326.30078
Reactions
S-(2-hydroxyacyl)glutathione + H(2)O → glutathione + a 2-hydroxy carboxylate.
Protein Details
2. 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:
GLO4
Uniprot ID:
Q12320
Molecular weight:
32338.59961
Reactions
S-(2-hydroxyacyl)glutathione + H(2)O → glutathione + a 2-hydroxy carboxylate.
Protein Details
3. D-lactate dehydrogenase [cytochrome] 1, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Catalyzes the stereospecific oxidation of D-lactate to pyruvate
Gene Name:
DLD1
Uniprot ID:
P32891
Molecular weight:
65291.89844
Reactions
(R)-lactate + 2 ferricytochrome c → pyruvate + 2 ferrocytochrome c.
Protein Details
4. D-lactate dehydrogenase [cytochrome] 3
General function:
Involved in catalytic activity
Specific function:
(R)-lactate + 2 ferricytochrome c = pyruvate + 2 ferrocytochrome c
Gene Name:
DLD3
Uniprot ID:
P39976
Molecular weight:
55224.5
Reactions
(R)-lactate + 2 ferricytochrome c → pyruvate + 2 ferrocytochrome c.
Protein Details
5. D-lactate dehydrogenase [cytochrome] 2, mitochondrial
General function:
Involved in catalytic activity
Specific function:
In addition to its enzymatic role it could play an important role in the yeast cell morphology
Gene Name:
DLD2
Uniprot ID:
P46681
Molecular weight:
59268.0
Reactions
(R)-lactate + 2 ferricytochrome c → pyruvate + 2 ferrocytochrome c.
Protein Details
6. Cytochrome c iso-1
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
Protein Details
7. Cytochrome c iso-2
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

Protein Details
1. Carboxylic acid transporter protein homolog
General function:
Involved in carbohydrate transmembrane transporter activity
Specific function:
Essential to lactate transport
Gene Name:
JEN1
Uniprot ID:
P36035
Molecular weight:
69375.60156