Ferroptosis-centered Drug Response Information

General Information of the Drug (ID: ferrodrug0102)
Name
Oleanolic acid
Synonyms
OLEANOLIC ACID; 508-02-1; Oleanic acid; Caryophyllin; Astrantiagenin C; Giganteumgenin C; Virgaureagenin B; Oleanol; 3beta-Hydroxyolean-12-en-28-oic acid; oleonolic acid; CCRIS 6493; NSC-114945; UNII-6SMK8R7TGJ; 6SMK8R7TGJ; Gledigenin 1; EINECS 208-081-6; (3-beta)-3-Hydroxyolean-12-en-28-oic acid; (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid; CHEBI:37659; NSC114945; 3-beta-Hydroxyolean-12-en-28-oic acid; Olean-12-en-28-oic acid, 3-hydroxy-, (3beta)-; Olean-12-en-28-oic acid, 3beta-hydroxy-; Olean-12-en-28-oic acid, 3-beta-hydroxy-; DTXSID50858790; NSC 114945; Olean-12-en-28-oic acid, 3-hydroxy-, (3-beta)-; (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid; OleanolicAcid; OLEANOLIC ACID (USP-RS); OLEANOLIC ACID [USP-RS]; MFCD00064914; (4aS,5S,6aS,6bR,8R,8aR,10S,12aR,12bR,14bS)-10-Hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid; SMR000445561; OLEANOLIC_ACID; CHEMBL168; (3.beta.)-3-Hydroxyolean-12-en-28-oic acid; Olean-12-en-28-oic acid, 3-hydroxy-, (3.beta.)-; oleanolic-acid; OleanolsA currencyure; Oleanoic Acid Hydrate; Olean-12-en-28-oic acid, 3.beta.-hydroxy-; Oleanolic acid, >=97%; OLEANOLIC ACID [MI]; SCHEMBL71070; MLS000697656; MLS002207133; OLEANOLIC ACID [INCI]; GTPL3306; OLEANOLIC ACID [WHO-DD]; MIJYXULNPSFWEK-GTOFXWBISA-N; DTXCID701474453; HMS2232D15; Oleanolic acid (OA)(Compound 1); Oleanolic acid, analytical standard; (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid; EX-A1991; HY-N0156; BDBM50346601; 3-beta-Hydroxyolean-12-en-28-oate; 3beta-hydroxy-Olean-12-en-28-oate; AKOS015951416; AC-8026; CCG-208530; CS-3800; LMPR0106150004; 3.beta.-hydroxy-Olean-12-en-28-oate; 3beta-hydroxy-Olean-12-en-28-oic acid; NCGC00017222-10; (2S,5S,10S,18S,1R,14R,15R,20R)-18-hydroxy-1,2,8,8,15,19,19-heptamethylpentacyc lo[12.8.0.0<2,11>.0<5,10>.0<15,20>]docos-11-ene-5-carboxylic acid; AS-35338; BP-25410; (3-beta)-3-Hydroxyolean-12-en-28-oate; (3?)-3-Hydroxyolean-12-en-28-oic acid; 3.beta.-hydroxy-Olean-12-en-28-oic acid; (3beta)-3-hydroxyolean-12-en-28-oic acid; (3.beta.)-3-hydroxy-Olean-12-en-28-oate; C17148; EN300-342251; (3.beta.)-3-hydroxy-Olean-12-en-28-oic acid; (3.beta.)-3-beta-hydroxy-Olean-12-en-28-oate; 3.BETA.-HYDROXYOLEAN-12-EN-28-OIC ACID; Olean-12-en-28-oic acid, 3-hydroxy-, (3b)-; Q418628; OLEANOLIC ACID (CONSTITUENT OF BANABA LEAF); Q-100572; (3.beta.)-3-beta-hydroxy-Olean-12-en-28-oic acid; OLEANOLIC ACID (CONSTITUENT OF HOLY BASIL LEAF); Oleanolic acid, primary pharmaceutical reference standard; C7EE6ACC-7175-4947-B524-FF8479525DA1; OLEANOLIC ACID (CONSTITUENT OF BANABA LEAF) [DSC]; OLEANOLIC ACID (CONSTITUENT OF HOLY BASIL LEAF) [DSC]; Oleanolic acid, European Pharmacopoeia (EP) Reference Standard; Oleanolic acid, United States Pharmacopeia (USP) Reference Standard; (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylicacid

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Status
Investigative
Drug Type
Small molecular drug
Structure
Formula
C30H48O3
IUPAC Name
(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Canonical SMILES
CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1)C)C(=O)O)C
InChI
InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30-/m0/s1
InChIKey
MIJYXULNPSFWEK-GTOFXWBISA-N
PubChem CID
10494
TTD Drug ID
D0SJ2Q
Full List of Ferroptosis Target Related to This Drug
Long-chain-fatty-acid--CoA ligase 4 (ACSL4)
 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 Driver
Responsed Disease Cervical cancer ICD-11: 2C77
 Disease Info 
Pathway Response Fatty acid metabolism hsa01212
Ferroptosis hsa04216
Cell Process Cell ferroptosis
Cell proliferation
In Vitro Model HeLa cells Endocervical adenocarcinoma Homo sapiens CVCL_0030
In Vivo Model
Male BALB/c Nude mice (20 ± 2g, 5 weeks old) were supplied by Hangzhou Ziyuan Experimental Animal Technology Co. LTD (SYXK-20180049) for this study. The nude mice were kept under specefic pathogen free (SPF) conditions for one week, and 5x107 Hela cells were injected under the left axillary skin after acclimatization. The tumors of Hela cell-inoculated mice were measured every 3 days after modeling, and tumor>=0.5 cm in diameter were considered successful. The tumor-bearing mice were randomly divided into control group (n = 6), 40 mg/kg OA group (n = 6) and 80 mg/kg OA group (n = 6). 40 mg/kg OA group and 80 mg/kg OA group both received subcutaneous injection modeling and control mice received saline intraperitoneal injections. The 40 mg/kg OA group and 80 mg/kg OA group received daily intraperitoneal injections of 40 mg/kg OA and 80 mg/kg OA for 15 days.

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Response regulation Oleanolic acid (OA) significantly reduced the viability and proliferative capacity of Hela cells. OA activated ferroptosis in Hela cells by promoting ACSL4 expression, thereby reducing the survival rate of Hela cells. Therefore, promotion of ACSL4-dependent ferroptosis by OA may be a potential approach for the treatment of cervical cancer.
References
Ref 1 Oleanolic acid inhibits cervical cancer Hela cell proliferation through modulation of the ACSL4 ferroptosis signaling pathway. Biochem Biophys Res Commun. 2021 Mar 19;545:81-88. doi: 10.1016/j.bbrc.2021.01.028. Epub 2021 Feb 3.