Showing Compound Card for L-Lactic acid (CDB004817)

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Record Information
Version1.0
Created at2020-04-17 18:39:49 UTC
Updated at2022-12-13 23:36:27 UTC
CannabisDB IDCDB004817
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameL-Lactic acid
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). Within humans, L-lactic acid participates in a number of enzymatic reactions. In particular, L-lactic acid can be biosynthesized from pyruvic acid through the action of 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 humans, L-lactic acid is involved in the metabolic disorder called the glutaminolysis and cancer pathway. L-Lactic acid is an acidic and odorless tasting compound. Outside of the human body, L-Lactic acid is found, on average, in the highest concentration within beers and milk (cow). L-Lactic acid has also been detected, but not quantified in, several different foods, such as cow milks, cow milks, cow milks, cow milks, and port wines. This could make L-lactic acid a potential biomarker for the consumption of these foods. L-Lactic acid is a potentially toxic compound. An optically active form of lactic acid having (S)-configuration. L-Lactic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-Lactic acidChEBI
(S)-(+)-Lactic acidChEBI
(S)-2-Hydroxypropanoic acidChEBI
(S)-2-Hydroxypropionic acidChEBI
L-(+)-alpha-Hydroxypropionic acidChEBI
L-(+)-Lactic acidChEBI
L-MilchsaeureChEBI
L-LactateKegg
(+)-LactateGenerator
(S)-(+)-LactateGenerator
(S)-2-HydroxypropanoateGenerator
(S)-2-HydroxypropionateGenerator
L-(+)-a-HydroxypropionateGenerator
L-(+)-a-Hydroxypropionic acidGenerator
L-(+)-alpha-HydroxypropionateGenerator
L-(+)-Α-hydroxypropionateGenerator
L-(+)-Α-hydroxypropionic acidGenerator
L-(+)-LactateGenerator
(alpha)-LactateHMDB
(alpha)-Lactic acidHMDB
(S)-(+)-2-HydroxypropanoateHMDB
(S)-(+)-2-Hydroxypropanoic acidHMDB
(S)-2-Hydroxy-propanoateHMDB
(S)-2-Hydroxy-propanoic acidHMDB
(S)-LactateHMDB
(S)-Lactic acidHMDB
1-Hydroxyethane 1-carboxylateHMDB
1-Hydroxyethane 1-carboxylic acidHMDB
1-HydroxyethanecarboxylateHMDB
1-Hydroxyethanecarboxylic acidHMDB
2-HydroxypropanoateHMDB
2-Hydroxypropanoic acidHMDB
2-HydroxypropionateHMDB
a-HydroxypropanoateHMDB
a-Hydroxypropanoic acidHMDB
a-HydroxypropionateHMDB
a-Hydroxypropionic acidHMDB
alpha-HydroxypropanoateHMDB
alpha-Hydroxypropanoic acidHMDB
alpha-HydroxypropionateHMDB
alpha-Hydroxypropionic acidHMDB
L-(+)- Lactic acidHMDB
L-2-HydroxypropanoateHMDB
L-2-Hydroxypropanoic acidHMDB
LactateHMDB
Lactic acidHMDB
Milk acidHMDB
Sarcolactic acidHMDB
2-Hydroxypropionic acidHMDB
D-Lactic acidHMDB
D Lactic acidHMDB
Lactate, ammoniumHMDB
2 Hydroxypropanoic acidHMDB
2 Hydroxypropionic acidHMDB
Ammonium lactateHMDB
L Lactic acidHMDB
D-LactateHMDB
L-Lactic acidChEBI
Chemical FormulaC3H6O3
Average Molecular Weight90.08
Monoisotopic Molecular Weight90.0317
IUPAC Name(2S)-2-hydroxypropanoic acid
Traditional Name(α)-lactate
CAS Registry Number79-33-4
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-/m0/s1
InChI KeyJVTAAEKCZFNVCJ-REOHCLBHSA-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 effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Indirect biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point16.8 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-002b-9000000000-50213d6b39ef9741c4662014-09-20View Spectrum
GC-MSL-Lactic acid, non-derivatized, GC-MS Spectrumsplash10-00kb-0900000000-fb59ec16914501aa19abSpectrum
GC-MSL-Lactic acid, non-derivatized, GC-MS Spectrumsplash10-014j-0900000000-c4d9e12b4b0150eda54bSpectrum
GC-MSL-Lactic acid, non-derivatized, GC-MS Spectrumsplash10-00kb-0900000000-fb59ec16914501aa19abSpectrum
Predicted GC-MSL-Lactic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-a3691f383d440fb00e1fSpectrum
Predicted GC-MSL-Lactic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01b9-9620000000-f7faa7db9c1be3d9d975Spectrum
Predicted GC-MSL-Lactic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Lactic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Lactic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Lactic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Lactic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Lactic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-9000000000-1d5a5f55463acefb6fc72012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000m-9000000000-c07133799d8f43d4c75a2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-000i-9000000000-ddb080250741e69ab1372012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-8f5d5eddb0b4b2a3b5412012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-3bcfc4cdc49230f156422012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-48b511409f4f60cec04e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-365ea3c1bcfff2cab9382012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-9d0238aeeb837213e81d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-8f5d5eddb0b4b2a3b5412017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-3bcfc4cdc49230f156422017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-48b511409f4f60cec04e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-365ea3c1bcfff2cab9382017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-9d0238aeeb837213e81d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-014i-9000000000-046bb7f6cce9744388eb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000f-9000000000-1c6ea519686b2066052f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9000000000-013763552dec660fac8c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-bc4403a40640361e5a522021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-9000000000-5f417f4a6d08f0ab00ed2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-9000000000-df7a94bb1a9cf6e78e1a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-9000000000-dc2a1b965287b9dfee9c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-c3686a681cc9bbf039e12016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-ddad20647c2ac56efd222016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-b728b45617afcc6b67da2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-b586cb8f053eb4465b4e2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-400a5f1c0dfcc32ef2bb2021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
L-lactate dehydrogenase A-like 6ALDHAL6A11p15.1Q6ZMR3 details
L-lactate dehydrogenase B chainLDHB12p12.2-p12.1P07195 details
L-lactate dehydrogenase C chainLDHC11p15.1P07864 details
L-lactate dehydrogenase A chainLDHA11p15.4P00338 details
L-lactate dehydrogenase A-like 6BLDHAL6B15q22.2Q9BYZ2 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.0221 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.00989 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.0400 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.0182 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.0132 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.0443 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0000190
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003294
KNApSAcK IDC00001191
Chemspider ID96860
KEGG Compound IDC00186
BioCyc IDL-LACTATE
BiGG ID34179
Wikipedia LinkLactic_Acid
METLIN ID5205
PubChem Compound107689
PDB IDNot Available
ChEBI ID422
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. L-lactate dehydrogenase A-like 6A
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Displays an lactate dehydrogenase activity. Significantly increases the transcriptional activity of JUN, when overexpressed.
Gene Name:
LDHAL6A
Uniprot ID:
Q6ZMR3
Molecular weight:
36507.015
Enzyme Details
2. L-lactate dehydrogenase B chain
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Not Available
Gene Name:
LDHB
Uniprot ID:
P07195
Molecular weight:
36638.225
Enzyme Details
3. L-lactate dehydrogenase C chain
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Possible role in sperm motility.
Gene Name:
LDHC
Uniprot ID:
P07864
Molecular weight:
36310.965
Enzyme Details
4. L-lactate dehydrogenase A chain
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Not Available
Gene Name:
LDHA
Uniprot ID:
P00338
Molecular weight:
30204.975
Enzyme Details
5. L-lactate dehydrogenase A-like 6B
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Not Available
Gene Name:
LDHAL6B
Uniprot ID:
Q9BYZ2
Molecular weight:
41942.53