D-Lactic acid
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Identification
- Generic Name
- D-Lactic acid
- DrugBank Accession Number
- DB03066
- Background
A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed)
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 90.0779
Monoisotopic: 90.031694058 - Chemical Formula
- C3H6O3
- Synonyms
- (−)-lactic acid
- (R)-(−)-lactic acid
- (R)-lactic acid
- D-2-Hydroxypropanoic acid
- D-2-Hydroxypropionic acid
- D-Milchsäure
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism U(S)-2-haloacid dehalogenase Not Available Pseudomonas 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
Pathway Category Pyruvate Kinase Deficiency Disease Pyruvate Metabolism Metabolic Leigh Syndrome Disease Pyruvate Dehydrogenase Complex Deficiency Disease Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency) Disease Pyruvaldehyde Degradation Metabolic Primary Hyperoxaluria II, PH2 Disease - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Alcohol / Aliphatic acyclic compound / Alpha-hydroxy acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- 2-hydroxypropanoic acid (CHEBI:42111)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 3Q6M5SET7W
- CAS number
- 10326-41-7
- 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[C@@H](O)C(O)=O
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
- HMDB0001311
- KEGG Compound
- C00256
- PubChem Compound
- 61503
- PubChem Substance
- 46505962
- ChemSpider
- 55423
- BindingDB
- 50420196
- 1742994
- ChEBI
- 42111
- ChEMBL
- CHEMBL358850
- ZINC
- ZINC000004658562
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- LAC
- PDB Entries
- 1c0k / 1c0q / 1c0r / 1p11 / 1p12 / 1qh9 / 1w3q / 2flt / 2fn7 / 2imp … show 33 more
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 52.8 °C PhysProp pKa 3.83 MERCK INDEX (1996) - Predicted Properties
Property Value Source Water Solubility 562.0 mg/mL ALOGPS logP -0.79 ALOGPS logP -0.47 Chemaxon logS 0.79 ALOGPS pKa (Strongest Acidic) 3.78 Chemaxon pKa (Strongest Basic) -3.7 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 57.53 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 18.84 m3·mol-1 Chemaxon Polarizability 8.05 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9487 Blood Brain Barrier + 0.7 Caco-2 permeable - 0.8957 P-glycoprotein substrate Non-substrate 0.7355 P-glycoprotein inhibitor I Non-inhibitor 0.9794 P-glycoprotein inhibitor II Non-inhibitor 0.9847 Renal organic cation transporter Non-inhibitor 0.958 CYP450 2C9 substrate Non-substrate 0.817 CYP450 2D6 substrate Non-substrate 0.9323 CYP450 3A4 substrate Non-substrate 0.7699 CYP450 1A2 substrate Non-inhibitor 0.9677 CYP450 2C9 inhibitor Non-inhibitor 0.8844 CYP450 2D6 inhibitor Non-inhibitor 0.9757 CYP450 2C19 inhibitor Non-inhibitor 0.9797 CYP450 3A4 inhibitor Non-inhibitor 0.9814 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.984 Ames test Non AMES toxic 0.9407 Carcinogenicity Non-carcinogens 0.5587 Biodegradation Ready biodegradable 0.8464 Rat acute toxicity 1.3737 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9911 hERG inhibition (predictor II) Non-inhibitor 0.9649
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 108.4665215 predictedDarkChem Lite v0.1.0 [M-H]- 108.4631215 predictedDarkChem Lite v0.1.0 [M-H]- 108.8024215 predictedDarkChem Lite v0.1.0 [M-H]- 108.6972215 predictedDarkChem Lite v0.1.0 [M-H]- 114.300446 predictedDeepCCS 1.0 (2019) [M-H]- 108.4665215 predictedDarkChem Lite v0.1.0 [M-H]- 108.4631215 predictedDarkChem Lite v0.1.0 [M-H]- 108.8024215 predictedDarkChem Lite v0.1.0 [M-H]- 108.6972215 predictedDarkChem Lite v0.1.0 [M-H]- 114.300446 predictedDeepCCS 1.0 (2019) [M+H]+ 110.2740215 predictedDarkChem Lite v0.1.0 [M+H]+ 110.6893215 predictedDarkChem Lite v0.1.0 [M+H]+ 109.1337215 predictedDarkChem Lite v0.1.0 [M+H]+ 109.0833215 predictedDarkChem Lite v0.1.0 [M+H]+ 117.1008 predictedDeepCCS 1.0 (2019) [M+H]+ 110.2740215 predictedDarkChem Lite v0.1.0 [M+H]+ 110.6893215 predictedDarkChem Lite v0.1.0 [M+H]+ 109.1337215 predictedDarkChem Lite v0.1.0 [M+H]+ 109.0833215 predictedDarkChem Lite v0.1.0 [M+H]+ 117.1008 predictedDeepCCS 1.0 (2019) [M+Na]+ 108.9649215 predictedDarkChem Lite v0.1.0 [M+Na]+ 108.6472215 predictedDarkChem Lite v0.1.0 [M+Na]+ 108.9489215 predictedDarkChem Lite v0.1.0 [M+Na]+ 108.7153215 predictedDarkChem Lite v0.1.0 [M+Na]+ 125.450485 predictedDeepCCS 1.0 (2019) [M+Na]+ 108.9649215 predictedDarkChem Lite v0.1.0 [M+Na]+ 108.6472215 predictedDarkChem Lite v0.1.0 [M+Na]+ 108.9489215 predictedDarkChem Lite v0.1.0 [M+Na]+ 108.7153215 predictedDarkChem Lite v0.1.0 [M+Na]+ 125.450485 predictedDeepCCS 1.0 (2019)
Targets
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1. Details(S)-2-haloacid dehalogenase
- 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
Transporters
1. DetailsMonocarboxylate transporter 2
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
2. DetailsMonocarboxylate transporter 1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
3. DetailsMonocarboxylate transporter 4
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52