Ferroptosis-centered Drug Response Information

General Information of the Drug (ID: ferrodrug0111)
Name
Naringenin
Synonyms
naringenin; 480-41-1; Salipurol; (S)-Naringenin; (S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one; pelargidanon; naringetol; (2S)-Naringenin; salipurpol; Naringenine; Asahina; NARIGENIN; NSC 11855; CCRIS 5839; (-)-(2S)-Naringenin; C15H12O5; UNII-HN5425SBF2; NSC 34875; HN5425SBF2; CHEBI:17846; AI3-23355; Flavanone, 4',5,7-trihydroxy-; (S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; (-)-Naringenin; YSO1; EINECS 207-550-2; NSC-11855; 2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; CHEMBL9352; NARINGENIN, (-)-; 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2S)-; DTXSID1022392; (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one; 5,7,4'-Trihydroxyflavanone; (S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone; (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one; 5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-chroman-4-one; (-)-(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one; (R,S)-Naringenin; 5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one; NSC-34875; (S)-2,3-dihydo-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (S)-; SR-01000721771; (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one; 4',5,7-trihydroxyflavan-4-one; Nari; BE-14348A; 2uxu; 4deu; S-Dihydrogenistein; pelargidanon 1602; Spectrum_000247; 4eh3; NARINGENIN [MI]; Spectrum2_000325; Spectrum3_000567; Spectrum4_000124; Spectrum5_001423; NARINGENIN [INCI]; 4',5,7-triOH-Flavone; 4',5,7-Trihydroxyflavanon; SCHEMBL20570; BSPBio_001954; KBioGR_000508; KBioSS_000727; MLS000574861; BIDD:ER0116; DivK1c_000118; SPECTRUM1500746; SPBio_000329; 4',5, 7-Trihydroxyflavanone; DTXCID302392; BDBM23419; HMS500F20; KBio1_000118; KBio2_000727; KBio2_003295; KBio2_005863; KBio3_001454; FTVWIRXFELQLPI-ZDUSSCGKSA-N; NINDS_000118; (2S)-5,7,4'-trihydroxyflavone; AIDS001417; HMS2202M06; (2S)-4',5,7-trihydroxyflavanone; HY-N0100; TNP00287; (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one; CCG-38601; LMPK12140001; Phytochemistry 8: 127 (1969); s2394; AKOS016843490; CS-6421; DB03467; FS-4072; SDCCGMLS-0066570.P001; (2S)-4',5,7-trihydroxyflavan-4-one; IDI1_000118; NCGC00016457-01; NCGC00016457-02; NCGC00016457-03; NCGC00017346-01; NCGC00163598-01; AC-33954; CAS-480-41-1; Flavanone, 4',5,7-trihydroxy- (8CI); SMR000156272; FT-0617134; SW219329-1; C00509; EN300-303163; A827427; Q418374; Q-100666; SR-01000721771-3; SR-01000721771-4; BRD-K08832567-001-02-4; BRD-K08832567-001-06-5; 2,3-Dihydro-5,6-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 4H-1-Benzopyran-4-one,2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2S)-; 13308-00-4

    Click to Show/Hide
Structure
Formula
C15H12O5
IUPAC Name
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Canonical SMILES
C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O
InChI
InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1
InChIKey
FTVWIRXFELQLPI-ZDUSSCGKSA-N
PubChem CID
439246
Full List of Ferroptosis Target Related to This Drug
Nuclear factor erythroid 2-related factor 2 (NFE2L2)
 Target Info 
In total 1 item(s) under this Target
Experiment 1 Reporting the Ferroptosis-centered Drug Act on This Target [1]
Target for Ferroptosis Marker/Suppressor
Responsed Disease Ischemia/reperfusion injury ICD-11: DB98
 Disease Info 
Pathway Response Fatty acid metabolism hsa01212
Ferroptosis hsa04216
Cell Process Cell ferroptosis
In Vitro Model CHO-S/H9C2 cells Normal Cricetulus griseus CVCL_A0TS
In Vivo Model
20 Sprague Dawley (SD) rats (6-8 weeks, 200-220 g) were acquired from the Second Clinical College of Guangzhou University of Traditional Chinese Medicine, and were weighed, coded, and randomly assigned to experimental groups. Rats were divided into Sham group, MI/R group, MI/R +NAR (low dose, 10 mg/kg/d) group, and MI/R +NAR (high dose, 50 mg/kg/d) group. For MI/R model, rats were anaesthetized by intraperitoneal injection of 1% pentobarbital sodium (60 mg/kg) and then received mechanical ventilation from an animal ventilator after endotracheal intubation.

    Click to Show/Hide
Response regulation Naringenin alleviated MI/R-induced pathological damage, inflammation and lipid peroxidation in myocardial tissue of rats. NAR adjusted the NRF2 /System xc - /GPX4 axis and improved ferroptosis. In conclusion, NAR can alleviate myocardial ischemia-reperfusion injury by regulating the Nrf2/System xc-/GPX4 axis to inhibit ferroptosis.
References
Ref 1 Naringenin alleviates myocardial ischemia/reperfusion injury by regulating the nuclear factor-erythroid factor 2-related factor 2 (Nrf2) /System xc-/ glutathione peroxidase 4 (GPX4) axis to inhibit ferroptosis. Bioengineered. 2021 Dec;12(2):10924-10934. doi: 10.1080/21655979.2021.1995994.