Lipoic acid

Details

• Internal ID: 794b7d06-f1af-4700-a11e-a194fb7d5d92
• Taxonomy: Organoheterocyclic compounds > Dithiolanes > Lipoic acids and derivatives
• IUPAC Name: 5-[(3R)-dithiolan-3-yl]pentanoic acid
• SMILES (Canonical): C1CSSC1CCCCC(=O)O
• SMILES (Isomeric): C1CSS[C@@H]1CCCCC(=O)O
• InChI: InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1
• InChI Key: AGBQKNBQESQNJD-SSDOTTSWSA-N
• Popularity: 9,731 references in papers

Physical and Chemical Properties

• 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

• 1200-22-2
• (R)-lipoic acid
• (R)-5-(1,2-Dithiolan-3-yl)pentanoic acid
• (R)-alpha-Lipoic acid
• (R)-(+)-1,2-Dithiolane-3-pentanoic acid
• R-(+)-Thioctic acid
• Heparlipon
• (+)-alpha-Lipoic acid
• R-alpha-Lipoic acid
• Thioctic acid d-form
• D-Thioctic acid
• Berlition
• Thiogamma
• Lipoec
• Tiobec
• (R)-1,2-Dithiolane-3-pentanoic acid
• Tioctic Acid
• R-Lipoic acid
• (R)-(+)-lipoic acid
• (R)-6,8-thioctic acid
• 5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid
• 5-[(3R)-dithiolan-3-yl]pentanoic acid
• 1,2-Dithiolane-3-pentanoic acid, (3R)-
• (R)-1,2-Dithiolane-3-valeric Acid
• Thioderm
• (R)-(+)-Lipoate
• alpha-(+)-Lipoic acid
• Tiobec Retard
• R-Lipoate
• 1,2-Dithiolane-3R-pentanoic acid
• Byodinoral 300
• (r)-(+)-alpha-lipoic acid
• R-(+)-Lipoic acid
• R-LA
• UNII-VLL71EBS9Z
• MFCD01631142
• VLL71EBS9Z
• (R)-(+)-a-Lipoic acid
• (3R)-1,2-Dithiolane-3-pentanoic Acid
• R-(+)-alpha-Lipoic acid
• CHEMBL134342
• CHEBI:30314
• 1,2-Dithiolane-3-pentanoic acid, (R)-
• (+/-)-alpha-Lipoic acid
• acetate replacing factor
• DRG-0236
• Thioctanoic acid
• C8-H14-O2-S2
• 5-(1,2-dithiolan-3-yl)valerianesyre
• (+)-thioctic acid
• (R)-Thioctic Acid
• R-alpha Lipoic acid
• ARLIPOIC ACID
• Losartan/thioctic acid
• (+)-a-Lipoic acid
• Thioctic acid, d form
• delta-[3-(1,2-dithiacyclopentyl)]pentanoic acid
• (y)-alpha-Lipoic Acid
• (+)-|A-Lipoic acid
• (?)-alpha-Lipoic Acid
• (R)-5-(1,2-Dithiolan-3-yl)pentanoicacid
• R)-(+)--Lipoic acid
• D02EVF
• D05YSU
• SCHEMBL7924
• (+)- alpha -Lipoic acid
• ARLIPOIC ACID [INN]
• Lopac0_001129
• (R)-(+)-?-Lipoic Acid
• GTPL4822
• DTXSID20152651
• INV-144
• AGBQKNBQESQNJD-SSDOTTSWSA-N
• D-THIOCTIC ACID [WHO-DD]
• .ALPHA.-LIPOIC ACID, D-
• HMS3263B19
• THIOCTIC ACID D-FORM [MI]
• Tox21_501129
• BDBM50106731
• LMFA01130001
• s3998
• (R)-6,8-DITHIOOCTANOIC ACID
• AKOS015892879
• AC-8133
• CCG-205204
• CS-5076
• CS-O-30809
• DB00166
• LP01129
• SDCCGSBI-0051097.P002
• 5-[(3R)-3-dithiolanyl]pentanoic acid
• NCGC00094396-01
• NCGC00094396-02
• NCGC00094396-03
• NCGC00094396-04
• NCGC00094396-05
• NCGC00094396-06
• NCGC00261814-01
• AC-11124
• AS-11009
• HY-18733
• ( inverted question mark)-alpha-Lipoic Acid
• EU-0101129
• L0207
• (R)-(+)--Lipoic acid;R-(+)-Thioctic acid
• 1,2-Dithiolane-3-valeric acid (()-), ()-
• T 5625
• (R)-(+)-alpha-Lipoic acid, analytical standard
• EN300-7352963
• A804416
• SR-01000076163
• (R)-(+)-1,2-Dithiolane-3-pentanoic acid, 97%
• (R)-(+)-alpha-Lipoic acid, >=98.0% (HPLC)
• J-004243
• Q-201824
• SR-01000076163-1
• Q27887203
• Z1269228108
• ( inverted question mark)-1,2-Dithiolane-3-pentanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

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

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	1 nM	IC50	PMID: 18181565
CHEMBL1293237	P54132	Bloom syndrome protein	7943.3 nM; 7943.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL230	P35354	Cyclooxygenase-2	0 nM	IC50	PMID: 17976864
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	501.2 nM	Potency	via Super-PRED
CHEMBL1293298	Q01453	Peripheral myelin protein 22	33807.8 nM	Potency	via CMAUP
CHEMBL3401	O75469	Pregnane X receptor	2800 nM	EC50	PMID: 20966043
CHEMBL1293235	P02545	Prelamin-A/C	35481.3 nM; 354.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	891.3 nM; 891.3 nM	Potency; Potency	via Super-PRED; via CMAUP

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

• Liriodendron tulipifera
• Solanum lycopersicum

Cross-Links

• PubChem: 6112
• NPASS: NPC166287
• ChEMBL: CHEMBL134342
• LOTUS: LTS0102878
• wikiData: Q27887203