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alpha Lipoic acid

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 824c05e5-dd4f-49ef-bad4-8322fe5473fb
Taxonomy Organoheterocyclic compounds > Dithiolanes > Lipoic acids and derivatives
IUPAC Name 5-(dithiolan-3-yl)pentanoic acid
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)
InChI Key AGBQKNBQESQNJD-UHFFFAOYSA-N
Popularity 5,187 references in papers

Physical and Chemical Properties

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Molecular Formula C8H14O2S2
Molecular Weight 206.30 g/mol
Exact Mass 206.04352203 g/mol
Topological Polar Surface Area (TPSA) 87.90 Ų
XlogP 1.70
Atomic LogP (AlogP) 2.79
H-Bond Acceptor 3
H-Bond Donor 1
Rotatable Bonds 5

Synonyms

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dl-Thioctic acid
1077-28-7
alpha-Lipoic acid
5-(1,2-Dithiolan-3-yl)pentanoic acid
1,2-dithiolane-3-pentanoic acid
DL-alpha-Lipoic acid
alpha Lipoic Acid
Biletan
62-46-4
6,8-Thioctic acid
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of alpha Lipoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9821 98.21%
Caco-2 - 0.6593 65.93%
Blood Brain Barrier + 0.8000 80.00%
Human oral bioavailability + 0.6286 62.86%
Subcellular localzation Mitochondria 0.7380 73.80%
OATP2B1 inhibitior - 0.8483 84.83%
OATP1B1 inhibitior + 0.9473 94.73%
OATP1B3 inhibitior + 0.9480 94.80%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior - 0.8666 86.66%
P-glycoprotein inhibitior - 0.9729 97.29%
P-glycoprotein substrate - 0.9356 93.56%
CYP3A4 substrate - 0.6240 62.40%
CYP2C9 substrate + 0.6107 61.07%
CYP2D6 substrate - 0.8602 86.02%
CYP3A4 inhibition - 0.9365 93.65%
CYP2C9 inhibition - 0.9071 90.71%
CYP2C19 inhibition - 0.9025 90.25%
CYP2D6 inhibition - 0.9232 92.32%
CYP1A2 inhibition - 0.9046 90.46%
CYP2C8 inhibition - 0.9241 92.41%
CYP inhibitory promiscuity - 0.9301 93.01%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.7700 77.00%
Carcinogenicity (trinary) Non-required 0.6359 63.59%
Eye corrosion - 0.5711 57.11%
Eye irritation + 0.9629 96.29%
Skin irritation - 0.6292 62.92%
Skin corrosion - 0.8138 81.38%
Ames mutagenesis - 0.9600 96.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6324 63.24%
Micronuclear - 0.8500 85.00%
Hepatotoxicity + 0.5125 51.25%
skin sensitisation - 0.6998 69.98%
Respiratory toxicity + 0.6889 68.89%
Reproductive toxicity + 0.6133 61.33%
Mitochondrial toxicity - 0.5750 57.50%
Nephrotoxicity - 0.6675 66.75%
Acute Oral Toxicity (c) III 0.7853 78.53%
Estrogen receptor binding - 0.7272 72.72%
Androgen receptor binding - 0.8749 87.49%
Thyroid receptor binding - 0.8056 80.56%
Glucocorticoid receptor binding - 0.8662 86.62%
Aromatase binding - 0.7500 75.00%
PPAR gamma - 0.5284 52.84%
Honey bee toxicity - 0.9680 96.80%
Biodegradation + 0.5250 52.50%
Crustacea aquatic toxicity - 0.6900 69.00%
Fish aquatic toxicity + 0.7602 76.02%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 501.2 nM
 Potency
 via Super-PRED
CHEMBL2095174 Q9UBE0 SUMO-activating enzyme 620 nM
 IC50
 via Super-PRED
CHEMBL1947 P10828 Thyroid hormone receptor beta-1 891.3 nM
 Potency
 via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL4040 P28482 MAP kinase ERK2 96.68% 83.82%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.09% 96.09%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 90.94% 95.17%
CHEMBL2581 P07339 Cathepsin D 90.47% 98.95%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.00% 99.17%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 87.56% 93.00%
CHEMBL5255 O00206 Toll-like receptor 4 85.69% 92.50%
CHEMBL340 P08684 Cytochrome P450 3A4 85.58% 91.19%
CHEMBL221 P23219 Cyclooxygenase-1 85.18% 90.17%
CHEMBL4618 P09960 Leukotriene A4 hydrolase 82.75% 97.86%
CHEMBL4330 Q9NS75 Cysteinyl leukotriene receptor 2 82.45% 98.00%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 82.29% 95.50%
CHEMBL217 P14416 Dopamine D2 receptor 81.91% 95.62%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.36% 95.89%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Hyacinthoides non-scripta

Cross-Links

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PubChem 864
LOTUS LTS0084509
wikiData Q312229