Natural Product (NP) Details

General Information of the NP (ID: NP2665)
Name
Alpha lipoic acid
Synonyms
dl-Thioctic acid; thioctic acid; alpha-Lipoic acid; 1077-28-7; lipoic acid; 5-(1,2-Dithiolan-3-yl)pentanoic acid; DL-alpha-Lipoic acid; 1,2-dithiolane-3-pentanoic acid; alpha Lipoic Acid; Thioctacid; Biletan; 6,8-Thioctic acid; 6-Thioctic acid; Lipothion; dl-Lipoic acid; DL-6,8-Thioctic acid; Liposan; Thioctsan; Tioctacid; Rac-lipoate; 1,2-Dithiolane-3-valeric acid; 6,8-Dithiooctanoic acid; alpha-Liponsaeure; DL-6-Thioctic acid; Thioctic acid dl-form; 62-46-4; alpha-liponic acid; Thioktsaeure; Tioctidasi; (RS)-Lipoic acid; 5-(1,2-Dithiolan-3-yl)valeric acid; espa-lipon; 5-(Dithiolan-3-yl)valeric acid; Acetate-replacing factor; 5-(dithiolan-3-yl)pentanoic acid; 6,8-Thiotic acid; Thioctansaeure; 6-Thiotic acid; DL-1,2-Dithiolane 3-valeric acid; (+-)-Lipoic acid; MFCD00005474; Thioctsaeure; liponic acid; Thiooctic acid; DL-.alpha.-Lipoic acid; (+/-)-1,2-Dithiolane-3-pentanoic acid; DL-1,2-Dithiolane-3-valeric acid; lipoate; NSC 90788; Lipoic acid, alpha; NSC 628502; (RS)-thioctic acid; (+-)-1,2-Dithiolane-3-pentanoic acid; .alpha.-Liponic acid; CHEBI:16494; Lip(S2); DL-1,2-Dithiolan-3-valeriansaeure; (.+-.)-Lipoic acid; 1,2-DITHIOLANE-3-VALERIC ACID, (+-)-; (RS)-.alpha.-Lipoic acid; 5-[3-(1,2-dithiolanyl)]pentanoic acid; CHEMBL33864; (.+-.)-.alpha.-Lipoic acid; NSC90788; NSC-90788; NCGC00016032-06; DSSTox_CID_5508; Protogen A; (+/-)-alpha-Lipoic acid; DL-Thioctic acid, 98+%; DSSTox_RID_77816; DSSTox_GSID_25508; Berlition; Thiogamma; (R)-(+)-alpha-Lipoic acid;R-(+)-Thioctic acid; L-Thioctic acid; Thioktsaeure [German]; biomolipon; duralipon; Alipure; AlphaLipogamma; Thiotacid; biomo lipon; espa lipon; Alpha Lipogamma; Alpha-Lipogamma; Pyruvate oxidation factor; DL-Thiocticacid; Pleomix Alpha; Thioctacide T; Verla Lipon; AlphaLipon Stada; .alpha.-Lipoic acid; Alpha Lippon AL; alpha-Liponsaeure [German]; Alpha Lipon Stada; Alpha-Lipon Stada; 5-(1,2)Dithiolan-3-yl-pentanoic acid; 5-[1,2]Dithiolan-3-yl-pentanoic acid; Liponsaureratiopharm; alpha-lipon 300; SMR000058198; CAS-1077-28-7; Liponsaure-ratiopharm; 1189471-66-6; (+-)-Thioctic acid; alpha Liponsaure von ct; Tioctidasi acetate replacing factor; SR-01000737460; (RS)-alpha-Lipoic acid; EINECS 200-534-6; EINECS 214-071-2; (+-)-alpha-lipoic acid; BRN 0081853; BRN 0122410; Alpha Lipoic; Alphalipoic-acid; a-lipoic acid; DL-1,2-Dithiolan-3-valeriansaeure [German]; Thioctic acid [INN:BAN:JAN]; HSDB 7818; alpha-lipoic-acid; D,L-Lipoic acid; Thiotomin (TN); D,L-Thioctic acid; lipoic acid (LA); LIPOIC-ACID; Thioctic acid (JAN); ()-alpha-Lipoic acid; PubChem14559; Spectrum_001618; 5-(1,2-dithiolan-3-yl)-pentanoate; Thioctic acid, dl-form; R-(+)-alpaLipoic acid; 1,2-Dithiolane-3-pentanoic acid, (+-)-; Spectrum2_001605; Spectrum3_001188; Spectrum4_000217; Spectrum5_001298; (S)-(-)-Thiocticacid; (+/-)-a-Lipoic acid; cid_864; (.+-.)-Thioctic acid; Lipoic acid, alpha [NF]; ACMC-209ug2; bmse000542; Epitope ID:150922; (+/-)-?-Lipoic acid; (.+/-.)-Lipoic acid; ACMC-1BU44; SCHEMBL51065; BSPBio_002835; DL-Thioctic acid (oxidized); KBioGR_000853; KBioSS_002098; 5-19-07-00237 (Beilstein Handbook Reference); MLS000069736; MLS001332379; MLS001332380; MLS002153365; DivK1c_000912; SPECTRUM1503941; (R)-(+)- a-Lipoic acid; SPBio_001609; DTXSID7025508; BDBM10515; HMS502N14; KBio1_000912; KBio2_002098; KBio2_004666; KBio2_007234; KBio3_002335; NINDS_000912; thioctic acid (alpha-lipoic acid); HMS1922M22; HMS3649H08; HMS3885I16; Pharmakon1600-01503941; ACT14091; ALBB-030318; BCP13221; BCP14048; BCP18944; HY-N0492; Tox21_110285; Tox21_201808; Tox21_303092; BBL013878; CCG-39063; dl-1,2-Dithiolane-3-pentanoic acid; NSC628502; NSC758651; s3996; SBB003484; STK801969; ()-1,2-Dithiolane-3-pentanoic acid; AKOS000121582; AKOS016339634; Tox21_110285_1; AM84329; CS-4370; EBD2203019; KS-1322; LS40210; MCULE-1034910084; NSC-628502; NSC-758651; IDI1_000912; DL-THIOCTIC ACID (OXIDIZED) 25G; NCGC00016032-02; NCGC00016032-03; NCGC00016032-04; NCGC00016032-05; NCGC00016032-07; NCGC00016032-08; NCGC00016032-09; NCGC00016032-11; NCGC00090872-01; NCGC00090872-02; NCGC00090872-03; NCGC00090872-04; NCGC00090872-05; NCGC00256970-01; NCGC00259357-01; (+/-)-alpha-Lipoic acid, >=98.0%; AC-22673; AK-68233; AK-72974; BP-31070; NCI60_042014; O217; R)-(+)-; A-Lipoic acid OOEthyAoEthAEa; ST073359; SY010902; (R)-(+)-(c) paragraph sign-Lipoic acid; SBI-0051871.P002; 5-(1,2-Dithiolan-3-yl)pentanoic acid #; AB0010770; DB-050522; 1,2-Dithiolane-3-pentanoic acid, (+/-)-; 1,2-Dithiolane-3-valeric acid, (.+-.)-; FT-0622068; FT-0625429; FT-0670812; FT-0670813; L0058; 1,2-Dithiolane-3-pentanoic acid, (.+-.)-; 1,2-Dithiolane-3-valeric acid, (.+/-.)-; 1,2-Dithiolane-3-pentanoic acid, (.+/-.)-; 3049-EP2316827A1; C00725; D00086; J10446; M-5249; AB00052393_09; (+/-)?-?1,2-?Dithiolane-?3-?Pentanoic Acid; Q312229; 1,2-Dithiolane-3-pentanoic acid, (+-)- (9CI); J-002007; J-520421; SR-01000737460-2; SR-01000737460-6; F2191-0208; Thioctic acid, European Pharmacopoeia (EP) Reference Standard; (+/-)-alpha-Lipoic acid, BioReagent, cell culture tested, >=99%; (+/-)-alpha-Lipoic acid, synthetic, >=99% (titration), powder; 5,5-dideuterio-5-(3,4,4-trideuteriodithiolan-3-yl)pentanoic acid; Alpha Lipoic Acid, United States Pharmacopeia (USP) Reference Standard; (R)-(+)-1,2-Dithiolane-3-pentanoic acid; R-(+)-Thioctic acid; R-(+)-alpha-Lipoic acid; AfAE'A centa' notA inverted exclamation markAfasA'A; AfAE'Adaggeratrade mark?-Lipoic Acid; Thioctic acid containing impurity B, European Pharmacopoeia (EP) Reference Standard; Thioctic acid for system suitability, European Pharmacopoeia (EP) Reference Standard; Thioctic Acid;1,2-Dithiolane-3-pentanoic acid;5-(1,2-Dithiolan-3-yl)valeric acid
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Species Origin Spinacia oleracea ...     Click to Show/Hide
Spinacia oleracea
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Caryophyllales
Family: Chenopodiaceae
Genus: Spinacia
Species: Spinacia oleracea
Disease Parkinson's disease [ICD-11: 8A00] Investigative [1]
Structure
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2D MOL

3D MOL

    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C8H14O2S2
PubChem CID
864
Canonical SMILES
C1CSSC1CCCCC(=O)O
InChI
1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)
InChIKey
AGBQKNBQESQNJD-UHFFFAOYSA-N
CAS Number
CAS 1077-28-7
ChEBI ID
CHEBI:16494
Herb ID
HBIN033360
TTD Drug ID
D0P6PQ
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Radiation      Breast cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation		 Induction Apoptosis
                    In-vitro Model MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 ALA significantly promoted apoptotic cell death when combined with RT, as reflected by Annexin V staining, expression of apoptosis-related factors, mitochondrial damages as well as cell morphological changes and reduction of cell numbers.
Target and Pathway
Target(s) Acetylcholinesterase (AChE)  Molecule Info  [3]
Prostaglandin G/H synthase 2 (COX-2)  Molecule Info  [4]
BioCyc Aspirin-triggered lipoxin biosynthesis Click to Show/Hide
2 Aspirin triggered resolvin D biosynthesis
3 C20 prostanoid biosynthesis
4 Aspirin triggered resolvin E biosynthesis
KEGG Pathway Arachidonic acid metabolism Click to Show/Hide
2 Metabolic pathways
3 NF-kappa B signaling pathway
4 VEGF signaling pathway
5 TNF signaling pathway
6 Retrograde endocannabinoid signaling
7 Serotonergic synapse
8 Ovarian steroidogenesis
9 Oxytocin signaling pathway
10 Regulation of lipolysis in adipocytes
11 Leishmaniasis
12 Pathways in cancer
13 Chemical carcinogenesis
14 MicroRNAs in cancer
15 Small cell lung cancer
16 Glycerophospholipid metabolism
17 Cholinergic synapse
NetPath Pathway IL1 Signaling Pathway Click to Show/Hide
2 TSH Signaling Pathway
3 IL4 Signaling Pathway
4 TGF_beta_Receptor Signaling Pathway
5 IL5 Signaling Pathway
Panther Pathway Endothelin signaling pathway Click to Show/Hide
2 Inflammation mediated by chemokine and cytokine signaling pathway
3 Toll receptor signaling pathway
4 CCKR signaling map ST
5 Muscarinic acetylcholine receptor 1 and 3 signaling pathway
6 Muscarinic acetylcholine receptor 2 and 4 signaling pathway
7 Nicotinic acetylcholine receptor signaling pathway
Pathwhiz Pathway Arachidonic Acid Metabolism Click to Show/Hide
2 Phospholipid Biosynthesis
Pathway Interaction Database Calcineurin-regulated NFAT-dependent transcription in lymphocytes Click to Show/Hide
2 S1P1 pathway
3 C-MYB transcription factor network
4 Signaling mediated by p38-alpha and p38-beta
5 Calcium signaling in the CD4+ TCR pathway
6 ATF-2 transcription factor network
WikiPathways Prostaglandin Synthesis and Regulation Click to Show/Hide
2 Arachidonic acid metabolism
3 Aryl Hydrocarbon Receptor
4 Quercetin and Nf-kB/ AP-1 Induced Cell Apoptosis
5 Spinal Cord Injury
6 Integrated Pancreatic Cancer Pathway
7 Eicosanoid Synthesis
8 Selenium Micronutrient Network
9 Monoamine Transport
10 Biogenic Amine Synthesis
11 Acetylcholine Synthesis
References
Reference 1 Alpha-Lipoic acid alleviates ferroptosis in the MPP + -induced PC12 cells via activating the PI3K/Akt/Nrf2 pathway. Cell Biol Int. 2021 Feb;45(2):422-431.
Reference 2 Synergistic Tumoricidal Effects of Alpha-Lipoic Acid and Radiotherapy on Human Breast Cancer Cells via HMGB1. Cancer Res Treat. 2021 Jul;53(3):685-694.
Reference 3 Multi-target-directed ligands to combat neurodegenerative diseases. J Med Chem. 2008 Feb 14;51(3):347-72.
Reference 4 Investigations concerning the COX/5-LOX inhibiting and hydroxyl radical scavenging potencies of novel 4,5-diaryl isoselenazoles. Eur J Med Chem. 2008 Jun;43(6):1152-9.
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