CHEBI:173097 - liproxstatin-1

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ChEBI Name liproxstatin-1
ChEBI ID CHEBI:173097
Definition An azaspiro compound that is 1'H-spiro[piperidine-4,2'-quinoxaline] in which the hydrogen at position 3' is replaced by a (3-chlorobenzyl)amino group. It is a potent inhibitor of ferroptosis.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB12744611, eMolecules:16251679, ZINC000015862369
Download Molfile XML SDF
Formula C19H21ClN4
Net Charge 0
Average Mass 340.860
Monoisotopic Mass 340.14547
InChI InChI=1S/C19H21ClN4/c20-15-5-3-4-14(12-15)13-22-18-19(8-10-21-11-9-19)24-17-7-2-1-6-16(17)23-18/h1-7,12,21,24H,8-11,13H2,(H,22,23)
InChIKey YAFQFNOUYXZVPZ-UHFFFAOYSA-N
SMILES ClC1=CC(CNC2=NC3=CC=CC=C3NC22CCNCC2)=CC=C1
Roles Classification
Chemical Role(s): radical scavenger
A role played by a substance that can react readily with, and thereby eliminate, radicals.
antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): ferroptosis inhibitor
Any substance that inhibits the process of ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.
Application(s): cardioprotective agent
Any protective agent that is able to prevent damage to the heart.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing liproxstatin-1 (CHEBI:173097) has role antioxidant (CHEBI:22586)
liproxstatin-1 (CHEBI:173097) has role cardioprotective agent (CHEBI:77307)
liproxstatin-1 (CHEBI:173097) has role ferroptosis inhibitor (CHEBI:173084)
liproxstatin-1 (CHEBI:173097) has role radical scavenger (CHEBI:48578)
liproxstatin-1 (CHEBI:173097) is a azaspiro compound (CHEBI:35624)
liproxstatin-1 (CHEBI:173097) is a monochlorobenzenes (CHEBI:83403)
liproxstatin-1 (CHEBI:173097) is a organic heterotricyclic compound (CHEBI:26979)
liproxstatin-1 (CHEBI:173097) is a secondary amino compound (CHEBI:50995)
IUPAC Name
N-(3-chlorobenzyl)-1'H-spiro[piperidine-4,2'-quinoxalin]-3'-amine
Synonyms Sources
Lip-1 ChEBI
liproxstatin 1 ChEBI
liproxstatin1 ChEBI
N-[(3-chlorophenyl)methyl]-1'H-spiro[piperidine-4,2'-quinoxalin]-3'-amine IUPAC
Manual Xref Database
20387119 ChemSpider
View more database links
Registry Number Type Source
950455-15-9 CAS Registry Number ChEBI
Citations
Klobucar K, Côté JP, French S, Borrillo L, Guo ABY, Serrano-Wu MH, Lee KK, Hubbard B, Johnson JW, Gaulin JL, Magolan J, Hung DT, Brown ED (2021)
Chemical Screen for Vancomycin Antagonism Uncovers Probes of the Gram-Negative Outer Membrane.
ACS chemical biology 16, 929-942 [PubMed:33974796]
[show Abstract]
Tao N, Li K, Liu J, Fan G, Sun T (2021)
Liproxstatin-1 alleviates bleomycin-induced alveolar epithelial cells injury and mice pulmonary fibrosis via attenuating inflammation, reshaping redox equilibrium, and suppressing ROS/p53/α-SMA pathway.
Biochemical and biophysical research communications 551, 133-139 [PubMed:33735625]
[show Abstract]
Qu XF, Liang TY, Wu DG, Lai NS, Deng RM, Ma C, Li X, Li HY, Liu YZ, Shen HT, Chen G (2021)
Acyl-CoA synthetase long chain family member 4 plays detrimental role in early brain injury after subarachnoid hemorrhage in rats by inducing ferroptosis.
CNS neuroscience & therapeutics 27, 449-463 [PubMed:33314758]
[show Abstract]
Guo Y, Du J, Xiao C, Xiang P, Deng Y, Hei Z, Li X (2021)
Inhibition of ferroptosis-like cell death attenuates neuropathic pain reactions induced by peripheral nerve injury in rats.
European journal of pain (London, England) 25, 1227-1240 [PubMed:33497529]
[show Abstract]
Zhao X, Gao M, Liang J, Chen Y, Wang Y, Wang Y, Xiao Y, Zhao Z, Wan X, Jiang M, Luo X, Wang F, Sun X (2021)
SLC7A11 Reduces Laser-Induced Choroidal Neovascularization by Inhibiting RPE Ferroptosis and VEGF Production.
Frontiers in cell and developmental biology 9, 639851 [PubMed:33681224]
[show Abstract]
Chen J, Yang L, Geng L, He J, Chen L, Sun Q, Zhao J, Wang X (2021)
Inhibition of Acyl-CoA Synthetase Long-Chain Family Member 4 Facilitates Neurological Recovery After Stroke by Regulation Ferroptosis.
Frontiers in cellular neuroscience 15, 632354 [PubMed:33889074]
[show Abstract]
Li Y, Zeng X, Lu D, Yin M, Shan M, Gao Y (2021)
Erastin induces ferroptosis via ferroportin-mediated iron accumulation in endometriosis.
Human reproduction (Oxford, England) 36, 951-964 [PubMed:33378529]
[show Abstract]
Fan BY, Pang YL, Li WX, Zhao CX, Zhang Y, Wang X, Ning GZ, Kong XH, Liu C, Yao X, Feng SQ (2021)
Liproxstatin-1 is an effective inhibitor of oligodendrocyte ferroptosis induced by inhibition of glutathione peroxidase 4.
Neural regeneration research 16, 561-566 [PubMed:32985488]
[show Abstract]
Cao Y, Li Y, He C, Yan F, Li JR, Xu HZ, Zhuang JF, Zhou H, Peng YC, Fu XJ, Lu XY, Yao Y, Wei YY, Tong Y, Zhou YF, Wang L (2021)
Selective Ferroptosis Inhibitor Liproxstatin-1 Attenuates Neurological Deficits and Neuroinflammation After Subarachnoid Hemorrhage.
Neuroscience bulletin 37, 535-549 [PubMed:33421025]
[show Abstract]
Du J, Wang L, Huang X, Zhang N, Long Z, Yang Y, Zhong F, Zheng B, Lan W, Lin W, Ma W (2021)
Shuganning injection, a traditional Chinese patent medicine, induces ferroptosis and suppresses tumor growth in triple-negative breast cancer cells.
Phytomedicine : international journal of phytotherapy and phytopharmacology 85, 153551 [PubMed:33827043]
[show Abstract]
Southon A, Szostak K, Acevedo KM, Dent KA, Volitakis I, Belaidi AA, Barnham KJ, Crouch PJ, Ayton S, Donnelly PS, Bush AI (2020)
CuII (atsm) inhibits ferroptosis: Implications for treatment of neurodegenerative disease.
British journal of pharmacology 177, 656-667 [PubMed:31655003]
[show Abstract]
Chen Y, Zhang P, Chen W, Chen G (2020)
Ferroptosis mediated DSS-induced ulcerative colitis associated with Nrf2/HO-1 signaling pathway.
Immunology letters 225, 9-15 [PubMed:32540488]
[show Abstract]
Zheng Z, Tang D, Zhao L, Li W, Han J, Hu B, Nie G, He Y (2020)
Liproxstatin-1 Protects Hair Cell-Like HEI-OC1 Cells and Cochlear Hair Cells against Neomycin Ototoxicity.
Oxidative medicine and cellular longevity 2020, 1782659 [PubMed:33343803]
[show Abstract]
Guiney SJ, Adlard PA, Lei P, Mawal CH, Bush AI, Finkelstein DI, Ayton S (2020)
Fibrillar α-synuclein toxicity depends on functional lysosomes.
The Journal of biological chemistry 295, 17497-17513 [PubMed:33453994]
[show Abstract]
Chen X, Zhang B, Liu T, Feng M, Zhang Y, Zhang C, Yao W, Wan L (2019)
Liproxstatin-1 Attenuates Morphine Tolerance through Inhibiting Spinal Ferroptosis-like Cell Death.
ACS chemical neuroscience 10, 4824-4833 [PubMed:31682397]
[show Abstract]
Feng Y, Madungwe NB, Imam Aliagan AD, Tombo N, Bopassa JC (2019)
Liproxstatin-1 protects the mouse myocardium against ischemia/reperfusion injury by decreasing VDAC1 levels and restoring GPX4 levels.
Biochemical and biophysical research communications 520, 606-611 [PubMed:31623831]
[show Abstract]
Kajarabille N, Latunde-Dada GO (2019)
Programmed Cell-Death by Ferroptosis: Antioxidants as Mitigators.
International journal of molecular sciences 20, E4968 [PubMed:31597407]
[show Abstract]
Wenz C, Faust D, Linz B, Turmann C, Nikolova T, Bertin J, Gough P, Wipf P, Schröder AS, Krautwald S, Dietrich C (2018)
t-BuOOH induces ferroptosis in human and murine cell lines.
Archives of toxicology 92, 759-775 [PubMed:28975372]
[show Abstract]
Zilka O, Shah R, Li B, Friedmann Angeli JP, Griesser M, Conrad M, Pratt DA (2017)
On the Mechanism of Cytoprotection by Ferrostatin-1 and Liproxstatin-1 and the Role of Lipid Peroxidation in Ferroptotic Cell Death.
ACS central science 3, 232-243 [PubMed:28386601]
[show Abstract]
Sheng X, Shan C, Liu J, Yang J, Sun B, Chen D (2017)
Theoretical insights into the mechanism of ferroptosis suppression via inactivation of a lipid peroxide radical by liproxstatin-1.
Physical chemistry chemical physics : PCCP 19, 13153-13159 [PubMed:28489094]
[show Abstract]
Last Modified
27 May 2021