Dihydrolipoic Acid
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Identification
- Generic Name
- Dihydrolipoic Acid
- DrugBank Accession Number
- DB03760
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 208.341
Monoisotopic: 208.059171136 - Chemical Formula
- C8H16O2S2
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UGlycine cleavage system H protein, mitochondrial Not Available Humans UDihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrial Not Available Humans U[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 3, mitochondrial Not Available Humans UAminomethyltransferase Not Available Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099) - 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
- Not Available
- 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 medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Fatty Acyls
- Sub Class
- Fatty acids and conjugates
- Direct Parent
- Medium-chain fatty acids
- Alternative Parents
- Thia fatty acids / Monocarboxylic acids and derivatives / Carboxylic acids / Alkylthiols / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic acyclic compound / Alkylthiol / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Medium-chain fatty acid / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- dihydrolipoic acid (CHEBI:45230)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 00K1YL9Q69
- CAS number
- 462-20-4
- InChI Key
- IZFHEQBZOYJLPK-SSDOTTSWSA-N
- InChI
- InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)/t7-/m1/s1
- IUPAC Name
- (6R)-6,8-disulfanyloctanoic acid
- SMILES
- [H][C@](S)(CCS)CCCCC(O)=O
References
- Synthesis Reference
Martin Klatt, "Method for producing lipoic acid and dihydrolipoic acid." U.S. Patent US20040044227, issued March 04, 2004.
US20040044227- General References
- Not Available
- External Links
- KEGG Compound
- C02147
- PubChem Compound
- 9834298
- PubChem Substance
- 46508127
- ChemSpider
- 8010019
- BindingDB
- 16436
- ChEBI
- 45230
- ChEMBL
- CHEMBL1235647
- ZINC
- ZINC000003869601
- PDBe Ligand
- RED
- PDB Entries
- 1dxm / 1wor / 1y8n / 1y8o / 1y8p / 2pnr / 2q8i / 8tq0
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.103 mg/mL ALOGPS logP 2.24 ALOGPS logP 2.2 Chemaxon logS -3.3 ALOGPS pKa (Strongest Acidic) 4.91 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 55.94 m3·mol-1 Chemaxon Polarizability 23.27 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9464 Blood Brain Barrier + 0.8108 Caco-2 permeable - 0.5625 P-glycoprotein substrate Non-substrate 0.7794 P-glycoprotein inhibitor I Non-inhibitor 0.9791 P-glycoprotein inhibitor II Non-inhibitor 0.9427 Renal organic cation transporter Non-inhibitor 0.9149 CYP450 2C9 substrate Non-substrate 0.7662 CYP450 2D6 substrate Non-substrate 0.8649 CYP450 3A4 substrate Non-substrate 0.7601 CYP450 1A2 substrate Non-inhibitor 0.75 CYP450 2C9 inhibitor Non-inhibitor 0.8379 CYP450 2D6 inhibitor Non-inhibitor 0.9536 CYP450 2C19 inhibitor Non-inhibitor 0.9442 CYP450 3A4 inhibitor Non-inhibitor 0.952 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.946 Ames test Non AMES toxic 0.8632 Carcinogenicity Non-carcinogens 0.783 Biodegradation Ready biodegradable 0.8503 Rat acute toxicity 2.2957 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9515 hERG inhibition (predictor II) Non-inhibitor 0.9129
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0ki6-7900000000-b1ad1e3fbadb23cbbd47 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a6u-0910000000-9ec5111dff0ea7ab3e7b Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0290000000-cf7772104a28246d89a8 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0ac9-6920000000-5ba64ad4e2ea4b84a13e Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0v00-1900000000-f47953c8b22be181db49 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001l-9300000000-4626d6f7c606044014aa Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-9300000000-ca3419538b04eb934b85 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 141.79771 predictedDeepCCS 1.0 (2019) [M+H]+ 145.33159 predictedDeepCCS 1.0 (2019) [M+Na]+ 154.78163 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- The glycine cleavage system catalyzes the degradation of glycine. The H protein (GCSH) shuttles the methylamine group of glycine from the P protein (GLDC) to the T protein (GCST). Has a pivotal role in the lipoylation of enzymes involved in cellular energetics such as the mitochondrial dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex (DLAT), and the mitochondrial dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex (DLST) (PubMed:36190515)
- Specific Function
- aminomethyltransferase activity
- Gene Name
- GCSH
- Uniprot ID
- P23434
- Uniprot Name
- Glycine cleavage system H protein, mitochondrial
- Molecular Weight
- 18884.37 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
2. DetailsDihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrial
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- As part of the pyruvate dehydrogenase complex, catalyzes the transfers of an acetyl group to a lipoic acid moiety (Probable). The pyruvate dehydrogenase complex, catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links cytoplasmic glycolysis and the mitochondrial tricarboxylic acid (TCA) cycle (Probable)
- Specific Function
- dihydrolipoyllysine-residue acetyltransferase activity
- Gene Name
- DLAT
- Uniprot ID
- P10515
- Uniprot Name
- Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrial
- Molecular Weight
- 68996.03 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Inhibits pyruvate dehydrogenase activity by phosphorylation of the E1 subunit PDHA1, and thereby regulates glucose metabolism and aerobic respiration. Can also phosphorylate PDHA2. Decreases glucose utilization and increases fat metabolism in response to prolonged fasting, and as adaptation to a high-fat diet. Plays a role in glucose homeostasis and in maintaining normal blood glucose levels in function of nutrient levels and under starvation. Plays a role in the generation of reactive oxygen species
- Specific Function
- ATP binding
- Gene Name
- PDK3
- Uniprot ID
- Q15120
- Uniprot Name
- [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 3, mitochondrial
- Molecular Weight
- 46938.485 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
4. DetailsAminomethyltransferase
- Kind
- Protein
- Organism
- Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
- Pharmacological action
- Unknown
- General Function
- The glycine cleavage system catalyzes the degradation of glycine.
- Specific Function
- aminomethyltransferase activity
- Gene Name
- gcvT
- Uniprot ID
- Q9WY54
- Uniprot Name
- Aminomethyltransferase
- Molecular Weight
- 40332.235 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52