Ferroptosis-centered Drug Response Information

General Information of the Drug (ID: ferrodrug0092)
Name
Ursolic Acid
Synonyms
Ursolic acid; 77-52-1; Prunol; Malol; Urson; 3beta-Hydroxyurs-12-en-28-oic acid; Micromerol; (3beta)-3-Hydroxyurs-12-en-28-oic acid; (+)-Ursolic acid; NSC-4060; CCRIS 7123; CHEBI:9908; NSC 167406; ursolic-acid; EINECS 201-034-0; NSC-167406; UNII-P3M2575F3F; AI3-03109; HSDB 7685; P3M2575F3F; CHEMBL169; Urs-12-en-28-oic acid, 3beta-hydroxy-; NSC 4060; .beta.-Ursolic acid; (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid; Bungeolic acid; URSOLIC ACID (USP-RS); URSOLIC ACID [USP-RS]; 3beta-Hydroxy-12-ursen-28-ic acid; NSC4060; Prunol;Urson;Malol; MFCD00009621; SMR000445681; SR-01000779684; Urs-12-en-28-oic acid, 3-hydroxy-, (3.beta.)-; TNP00103; (3 beta)-3-hydroxyurs-12-en-28-oic acid; 6Q5; Urs-12-en-28-oic acid, 3-hydroxy-, (3beta)-; 3beta-hydroxy-Urs-12-en-28-oic acid; 3B-HYDROXYURS-12-EN-28-OIC ACID; Prestwick3_000089; Ursolic acid, >=90%; URSOLIC ACID [MI]; URSOLIC ACID [HSDB]; URSOLIC ACID [INCI]; SCHEMBL70205; BSPBio_000018; MLS000728569; MLS002154196; MLS002207073; URSOLIC ACID [WHO-DD]; BPBio1_000020; N-Ethylhydroxylaminehydrochloride; DTXSID70883221; Ursolic acid, analytical standard; WCGUUGGRBIKTOS-GPOJBZKASA-N; 3beta-Hydroxyurs-12-en-28-oate; HMS2095A20; HMS2231P19; (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,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; 3beta-hydroxy-Urs-12-en-28-oate; HY-N0140; BDBM50148911; 3beta-Hydroxy-12-ursen-28-oic Acid; AKOS005228010; AKOS016023773; 3.beta.-hydroxy-Urs-12-en-28-oate; CCG-208282; CS-3799; DB15588; LMPR0106180007; (3beta)-3-Hydroxyurs-12-en-28-oate; (3beta)-3-hydroxy-Urs-12-en-28-oate; AS-35119; 3.beta.-hydroxy-Urs-12-en-28-oic acid; (3beta)-3-hydroxy-Urs-12-en-28-oic acid; AB00513802; U0065; C08988; A839123; Q416260; Q-201916; SR-01000779684-4; SR-01000779684-5; (3.BETA.)-3-HYDROXYURS-12-EN-28-OIC ACID; BRD-K68185022-001-02-3; BRD-K68185022-001-14-8; URSOLIC ACID (CONSTITUENT OF HOLY BASIL LEAF); Ursolic acid, primary pharmaceutical reference standard; AF479D19-631E-48F1-8ABA-FB2A806046FA; URSOLIC ACID (CONSTITUENT OF HOLY BASIL LEAF) [DSC]; (3beta,5beta,18alpha,20beta)-3-hydroxyurs-12-en-28-oic acid; Ursolic acid, European Pharmacopoeia (EP) Reference Standard; '(3beta,5beta,18alpha,20beta)-3-hydroxyurs-12-en-28-oic acid'; Ursolic acid, United States Pharmacopeia (USP) Reference Standard; (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylicacid

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Structure
Formula
C30H48O3
IUPAC Name
(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Canonical SMILES
CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1C)C)C(=O)O
InChI
InChI=1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1
InChIKey
WCGUUGGRBIKTOS-GPOJBZKASA-N
PubChem CID
64945
Full List of Ferroptosis Target Related to This Drug
Ferritin light chain (FTL)
 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 Suppressor
Responsed Disease Osteosarcoma ICD-11: 2B51
 Disease Info 
Pathway Response Ferroptosis hsa04216
Autophagy hsa04140
Apoptosis hsa04210
Cell Process Cell ferroptosis
Cell proliferation
Cell apoptosis
Cell autophagy
In Vitro Model HOS cells Osteosarcoma Homo sapiens CVCL_0312
143B cells Osteosarcoma Homo sapiens CVCL_2270
In Vivo Model
NU/NU mice (the Fourth Military Medical University, Shaanxi, China) were injected with 143B cells (100 uL, 5 x 107 cells/mL, i.h.). Seven days after the injection, the mice were divided into 6 different groups (n= 3) and intraperitoneally injected with different drugs twice a week. Then, on day 28, the mice were sacrificed, and the tumours in the different groups were weighed. Body weight and tumour size were measured every 3 days from day 7 to day 28. The tumour tissue was fixed with 4% paraformaldehyde, embedded in paraffin, and cut into 4 um thick sections for haematoxylin-eosin (H&E) and immunofluorescence staining.

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Response regulation Ursolic acid inhibited tumour cell proliferation and promoted the apoptosis of a variety of osteosarcoma cells. Mechanistic studies showed that ursolic acid degraded ferritin by activating autophagy and induced intracellular overload of ferrous ions, leading to ferroptosis. Ferritin, which includes ferritin light peptide 1 (FTL1) and ferritin heavy peptide 1 (FTH1).
Ferritin heavy chain (FTH1)
 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 Osteosarcoma ICD-11: 2B51
 Disease Info 
Pathway Response Ferroptosis hsa04216
Autophagy hsa04140
Apoptosis hsa04210
Cell Process Cell ferroptosis
Cell proliferation
Cell apoptosis
Cell autophagy
In Vitro Model HOS cells Osteosarcoma Homo sapiens CVCL_0312
143B cells Osteosarcoma Homo sapiens CVCL_2270
In Vivo Model
NU/NU mice (the Fourth Military Medical University, Shaanxi, China) were injected with 143B cells (100 uL, 5 x 107 cells/mL, i.h.). Seven days after the injection, the mice were divided into 6 different groups (n= 3) and intraperitoneally injected with different drugs twice a week. Then, on day 28, the mice were sacrificed, and the tumours in the different groups were weighed. Body weight and tumour size were measured every 3 days from day 7 to day 28. The tumour tissue was fixed with 4% paraformaldehyde, embedded in paraffin, and cut into 4 um thick sections for haematoxylin-eosin (H&E) and immunofluorescence staining.

    Click to Show/Hide
Response regulation Ursolic acid inhibited tumour cell proliferation and promoted the apoptosis of a variety of osteosarcoma cells. Mechanistic studies showed that ursolic acid degraded ferritin by activating autophagy and induced intracellular overload of ferrous ions, leading to ferroptosis. Ferritin, which includes ferritin light peptide 1 (FTL1) and ferritin heavy peptide 1 (FTH1).
References
Ref 1 The Synergistic Reducing Drug Resistance Effect of Cisplatin and Ursolic Acid on Osteosarcoma through a Multistep Mechanism Involving Ferritinophagy. Oxid Med Cell Longev. 2021 Dec 21;2021:5192271. doi: 10.1155/2021/5192271. eCollection 2021.