Identification

Name
D-Lactic acid
Accession Number
DB03066  (EXPT01215)
Type
Small Molecule
Groups
Experimental
Description

A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed)

Structure
Thumb
Synonyms
  • (−)-lactic acid
  • (R)-(−)-lactic acid
  • (R)-lactic acid
  • D-2-Hydroxypropanoic acid
  • D-2-Hydroxypropionic acid
  • D-Milchsäure
Categories
UNII
3Q6M5SET7W
CAS number
10326-41-7
Weight
Average: 90.0779
Monoisotopic: 90.031694058
Chemical Formula
C3H6O3
InChI Key
JVTAAEKCZFNVCJ-UWTATZPHSA-N
InChI
InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m1/s1
IUPAC Name
(2R)-2-hydroxypropanoic acid
SMILES
C[[email protected]@H](O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U(S)-2-haloacid dehalogenaseNot AvailablePseudomonas sp. (strain YL)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Pyruvate Dehydrogenase Complex DeficiencyDisease
Leigh SyndromeDisease
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)Disease
Pyruvate MetabolismMetabolic
Pyruvate kinase deficiencyDisease
Pyruvaldehyde DegradationMetabolic
Primary hyperoxaluria II, PH2Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Hartmut Voelskow, Dieter Sukatsch, "Process for the production of D-lactic acid with the use of Lactobacillus bulgaricus DSM 2129." U.S. Patent US4467034, issued May, 1979.

US4467034
General References
Not Available
External Links
Human Metabolome Database
HMDB01311
KEGG Compound
C00256
PubChem Compound
61503
PubChem Substance
46505962
ChemSpider
55423
BindingDB
50420196
ChEBI
42111
ChEMBL
CHEMBL358850
IUPHAR
2934
Guide to Pharmacology
GtP Drug Page
HET
LAC
PDB Entries
1c0k / 1c0q / 1c0r / 1p11 / 1p12 / 1qh9 / 1w3q / 2flt / 2fn7 / 2imp
show 16 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)52.8 °CPhysProp
pKa3.83MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility562.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity18.84 m3·mol-1ChemAxon
Polarizability8.05 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9487
Blood Brain Barrier+0.7
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.7355
P-glycoprotein inhibitor INon-inhibitor0.9794
P-glycoprotein inhibitor IINon-inhibitor0.9847
Renal organic cation transporterNon-inhibitor0.958
CYP450 2C9 substrateNon-substrate0.817
CYP450 2D6 substrateNon-substrate0.9323
CYP450 3A4 substrateNon-substrate0.7699
CYP450 1A2 substrateNon-inhibitor0.9677
CYP450 2C9 inhibitorNon-inhibitor0.8844
CYP450 2D6 inhibitorNon-inhibitor0.9757
CYP450 2C19 inhibitorNon-inhibitor0.9797
CYP450 3A4 inhibitorNon-inhibitor0.9814
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.984
Ames testNon AMES toxic0.9407
CarcinogenicityNon-carcinogens0.5587
BiodegradationReady biodegradable0.8464
Rat acute toxicity1.3737 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9911
hERG inhibition (predictor II)Non-inhibitor0.9649
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-000i-9000000000-704f8ff33156c82a02d1
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-000m-9000000000-023931446d9bb3330e7f
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-000l-9000000000-0fb29afb128baea2240b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-000i-9000000000-d7cd347946e49a57860e
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Hydroxy acids and derivatives
Sub Class
Alpha hydroxy acids and derivatives
Direct Parent
Alpha hydroxy acids and derivatives
Alternative Parents
Secondary alcohols / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
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
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
2-hydroxypropanoic acid (CHEBI:42111)

Targets

Kind
Protein
Organism
Pseudomonas sp. (strain YL)
Pharmacological action
Unknown
General Function
(s)-2-haloacid dehalogenase activity
Specific Function
Catalyzes the hydrolytic dehalogenation of small (S)-2-haloalkanoic acids to yield the corresponding (R)-2-hydroxyalkanoic acids. Acts on acids of short chain lengths, C(2) to C(4), with inversion ...
Gene Name
Not Available
Uniprot ID
Q53464
Uniprot Name
(S)-2-haloacid dehalogenase
Molecular Weight
26176.335 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucin...
Gene Name
SLC16A7
Uniprot ID
O60669
Uniprot Name
Monocarboxylate transporter 2
Molecular Weight
52199.745 Da
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Symporter activity
Specific Function
Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucin...
Gene Name
SLC16A1
Uniprot ID
P53985
Uniprot Name
Monocarboxylate transporter 1
Molecular Weight
53943.685 Da
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Symporter activity
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...
Gene Name
SLC16A3
Uniprot ID
O15427
Uniprot Name
Monocarboxylate transporter 4
Molecular Weight
49468.9 Da
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]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:22