Dihydrolipoic Acid

Identification

Name
Dihydrolipoic Acid
Accession Number
DB03760  (EXPT02769)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
00K1YL9Q69
CAS number
462-20-4
Weight
Average: 208.341
Monoisotopic: 208.059171136
Chemical Formula
C8H16O2S2
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][[email protected]](S)(CCS)CCCCC(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAminomethyltransferaseNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
UGlycine cleavage system H protein, mitochondrialNot AvailableHuman
UDihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrialNot AvailableHuman
U[Pyruvate dehydrogenase [lipoamide]] kinase isozyme 3, mitochondrialNot AvailableHuman
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
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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
HET
RED
PDB Entries
1dxm / 1wor / 1y8n / 1y8o / 1y8p / 2pnr / 2q8i

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.103 mg/mLALOGPS
logP2.24ALOGPS
logP2.2ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.91ChemAxon
pKa (Strongest Basic)-9.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity55.94 m3·mol-1ChemAxon
Polarizability23.27 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9464
Blood Brain Barrier+0.8108
Caco-2 permeable-0.5625
P-glycoprotein substrateNon-substrate0.7794
P-glycoprotein inhibitor INon-inhibitor0.9791
P-glycoprotein inhibitor IINon-inhibitor0.9427
Renal organic cation transporterNon-inhibitor0.9149
CYP450 2C9 substrateNon-substrate0.7662
CYP450 2D6 substrateNon-substrate0.8649
CYP450 3A4 substrateNon-substrate0.7601
CYP450 1A2 substrateNon-inhibitor0.75
CYP450 2C9 inhibitorNon-inhibitor0.8379
CYP450 2D6 inhibitorNon-inhibitor0.9536
CYP450 2C19 inhibitorNon-inhibitor0.9442
CYP450 3A4 inhibitorNon-inhibitor0.952
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.946
Ames testNon AMES toxic0.8632
CarcinogenicityNon-carcinogens0.783
BiodegradationReady biodegradable0.8503
Rat acute toxicity2.2957 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9515
hERG inhibition (predictor II)Non-inhibitor0.9129
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
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

Taxonomy

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
Medium-chain fatty acid / Thia fatty acid / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Alkylthiol / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organosulfur compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
dihydrolipoic acid (CHEBI:45230)

Targets

Kind
Protein
Organism
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
Transaminase activity
Specific Function
The glycine cleavage system catalyzes the degradation of glycine.
Gene Name
gcvT
Uniprot ID
Q9WY54
Uniprot Name
Aminomethyltransferase
Molecular Weight
40332.235 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]
  3. 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Aminomethyltransferase activity
Specific 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).
Gene Name
GCSH
Uniprot ID
P23434
Uniprot Name
Glycine cleavage system H protein, mitochondrial
Molecular Weight
18884.37 Da
References
  1. 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Dihydrolipoyllysine-residue acetyltransferase activity
Specific Function
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name
DLAT
Uniprot ID
P10515
Uniprot Name
Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrial
Molecular Weight
68996.03 Da
References
  1. 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Pyruvate dehydrogenase (acetyl-transferring) kinase activity
Specific 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 glucos...
Gene Name
PDK3
Uniprot ID
Q15120
Uniprot Name
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 3, mitochondrial
Molecular Weight
46938.485 Da
References
  1. 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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:18