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Identification
NameDihydrolipoic Acid
Accession NumberDB03760  (EXPT02769)
Typesmall molecule
Groupsexperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number462-20-4
WeightAverage: 208.341
Monoisotopic: 208.059171136
Chemical FormulaC8H16O2S2
InChI KeyInChIKey=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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassFatty Acids and Conjugates
SubclassThia Fatty Acids
Direct parentThia Fatty Acids
Alternative parentsPolyamines; Enolates; Carboxylic Acids; Alkylthiols
Substituentsenolate; polyamine; carboxylic acid; carboxylic acid derivative; alkylthiol
Classification descriptionThis compound belongs to the thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Non-inhibitor 0.8379
CYP450 2D6 substrate Non-inhibitor 0.9536
CYP450 2C19 substrate Non-inhibitor 0.9442
CYP450 3A4 substrate 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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility1.03e-01 g/lALOGPS
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 area37.3ChemAxon
rotatable bond count7ChemAxon
refractivity55.94ChemAxon
polarizability23.27ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Martin Klatt, “Method for producing lipoic acid and dihydrolipoic acid.” U.S. Patent US20040044227, issued March 04, 2004.

US20040044227
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC02147
PubChem Compound9834298
PubChem Substance46508127
ChemSpider8010019
BindingDB16436
ChEBI18047
ChEMBL
HETRED
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Aminomethyltransferase

Kind: protein

Organism: Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)

Pharmacological action: unknown

Components

Name UniProt ID Details
Aminomethyltransferase Q9WY54 Details

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
  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
  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

2. Glycine cleavage system H protein, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Glycine cleavage system H protein, mitochondrial P23434 Details

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

3. Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrial P10515 Details

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

4. [Pyruvate dehydrogenase [lipoamide]] kinase isozyme 3, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
[Pyruvate dehydrogenase [lipoamide]] kinase isozyme 3, mitochondrial Q15120 Details

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

Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:22