Ferroptosis-centered Drug Response Information

General Information of the Drug (ID: ferrodrug0087)
Name
Bilirubin
Synonyms
bilirubin; 635-65-4; Hematoidin; Hemetoidin; Bilirubin IX-alpha; Cholerythrin; Bilibubin; Bilirubin IX.alpha.; 3-[2-[[3-(2-carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid; Bilirubin IXalpha; RFM9X3LJ49; 21H-Biline-8,12-dipropanoic acid, 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-; (4z,15z)-bilirubin ix.alpha.; CHEBI:16990; 93891-87-3; Disodium bilirubinate IXalpha; NSC-26685; PHEOPHYTIN; Biline-8,12-dipropionic acid, 1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-; 1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionic acid; 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid; 3-(2-((3-(2-carboxyethyl)-4-methyl-5-((Z)-(3-methyl-5-oxo-4-vinyl-1H-pyrrol-2(5H)-ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-methyl-5-((Z)-(4-methyl-5-oxo-3-vinyl-1H-pyrrol-2(5H)-ylidene)methyl)-1H-pyrrol-3-yl)propanoic acid; Calcium bilirubinate; Basinite; EINECS 211-239-7; Bilirubin IX alpha; MFCD00005499; NSC 26685; UNII-RFM9X3LJ49; BRN 0074376; Bilirubin test; AI3-23078; CCRIS 9347; bilirubin-IXalpha; bilirubin(Z,Z); Bilirubin,(S); 3-[5-[(Z)-(4-Ethenyl-3-Methyl-5-Oxidanylidene-Pyrrol-2-Ylidene)methyl]-2-[[5-[(Z)-(3-Ethenyl-4-Methyl-5-Oxidanylidene-Pyrrol-2-Ylidene)methyl]-3-(3-Hydroxy-3-Oxopropyl)-4-Methyl-1h-Pyrrol-2-Yl]methyl]-4-Methyl-1h-Pyrrol-3-Yl]propanoic Acid; EINECS 299-468-9; Bilirubin, 98%; (Z,Z)-Bilirubin IXa; BILIRUBIN [MI]; Spectrum5_000410; bmse000627; BILIRUBIN [WHO-DD]; SCHEMBL19065; (4Z,15Z)-Bilirubin IXa; BSPBio_002531; 5-26-15-00523 (Beilstein Handbook Reference); SPECTRUM1500857; BILIRUBIN TEST [VANDF]; CHEMBL501680; GTPL4577; SCHEMBL5086205; DTXSID8060905; S00334a; BCP13520; HY-N0323; BDBM50442897; CCG-38548; HSCI1_000394; s5116; STL564421; AKOS015895627; Bilirubin, purum, >=95.0% (UV); SDCCGMLS-0066651.P001; NCGC00095645-01; 18422-02-1; 3-{2-({3-(2-Carboxyethyl)-4-methyl-5-[(Z)-(3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl]-1H-pyrrol-2-yl}methyl)-4-methyl-5-[(Z)-(4-methyl-5-ox; AC-20194; AC-34137; Disodium 1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-2,17-divinyl-21H-biline-8,12-dipropionate; CS-0008888; -ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-; -(3-methyl-5-oxo-4-vinyl-1H-pyrrol-2(5H); B-2500; B-2501; C00486; methyl-5-((Z)-(4-methyl-5-oxo-3-vinyl-1H-; 3-(2-((3-(2-carboxyethyl)-4-methyl-5-((Z); Bilirubin, >=98% (EmM/453 = 60), powder; Q104219; SR-05000002757; SR-05000002757-1; pyrrol-2(5H)-ylidene)methyl)-1H-pyrrol-3-yl)propanoic acid; 1,3,6,7-TETRAMETHYL-4,5-DICARBOXYETHYL-2,8-DIVINYL-(B-13)-DIHYDROBILENONE; 1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-Biline-8,12-dipropionate; 1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-Biline-8,12-dipropionic acid; 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-Biline-8,12-dipropanoate; 2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoic acid; 21H-Biline-8,12-dipropanoic acid, 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-, calcium salt; 21H-Biline-8,12-dipropanoic acid, 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-, disodium salt; 21H-Biline-8,12-dipropanoic acid,2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-; 3,18-diethenyl-2,7,13,17-tetramethyl-1,19-dioxo-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoic acid; 3-(2-((3-(2-carboxyethyl)-4-methyl-5-((3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-methyl-5-((4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-3-yl)propanoate; 3-(2-((3-(2-carboxyethyl)-4-methyl-5-((3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-methyl-5-((4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-3-yl)propanoic acid; 3-(2-((3-(2-carboxyethyl)-4-methyl-5-((Z)-(3-methyl-5-oxo-4-vinyl-1H-pyrrol-2(5H)-ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-methyl-5-((Z)-(4-methyl-5-oxo-3-vinyl-1H-pyrrol-2(5H)-ylidene)methyl)-1H-pyrr; 3-(2-((3-(2-carboxyethyl)-4-methyl-5-((Z)-(3-methyl-5-oxo-4-vinyl-1H-pyrrol-2(5H)-ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-methyl-5-((Z)-(4-methyl-5-oxo-3-vinyl-1H-pyrrol-2(5H)-ylidene)methyl)-1H-pyrrol-3-yl)propanoicacid; 3-(2-((3-(2-Carboxyethyl)-4-methyl-5-[(Z)-(3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl]-1H-pyrrol-2-yl)methyl)-4-methyl-5-[(Z)-(4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene; 3-(2-((3-(2-Carboxyethyl)-4-methyl-5-[(Z)-(3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl]-1H-pyrrol-2-yl)methyl)-4-methyl-5-[(Z)-(4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene #; 3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid; 3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid; 3-[2-[[3-(2-carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoate; 3-[2-[[3-(2-carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid; 3-[2-[[3-(2-carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoate; 3-[2-[[3-(2-carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid; 3-[2-[[3-(2-carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoicacid; 3-[2-[3-(2-Carboxy-ethyl)-4-methyl-5-(3-methyl-5-oxo-4-vinyl-1,5-dihydro-pyrrol-2-ylidenemethyl)-1H-pyrrol-2-ylmethyl]-4-methyl-5-(4-methyl-5-oxo-3-vinyl-1,5-dihydro-pyrrol-2-ylidenemethyl)-1H-pyrrol-; 3Q9; 8,12-bis(2-carboxyethyl)-2,7,13,17-tetramethyl-3,18-divinylbiladiene-ac-1,19(21H,24H)-dione; Bilirubin: 21H-Biline-8,12-dipropanoicacid,2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-,

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Status
Investigative
Drug Type
Small molecular drug
Structure
Formula
C33H36N4O6
IUPAC Name
3-[2-[[3-(2-carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid
Canonical SMILES
CC1=C(NC(=C1CCC(=O)O)CC2=C(C(=C(N2)C=C3C(=C(C(=O)N3)C)C=C)C)CCC(=O)O)C=C4C(=C(C(=O)N4)C=C)C
InChI
InChI=1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-
InChIKey
BPYKTIZUTYGOLE-IFADSCNNSA-N
PubChem CID
5280352
TTD Drug ID
D0O8ZV
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 Diabetes mellitus ICD-11: 5A10
 Disease Info 
Pathway Response Fatty acid metabolism hsa01212
Ferroptosis hsa04216
Cell Process Cell ferroptosis
In Vitro Model MIN6 cells Insulinoma Mus musculus CVCL_0431
In Vivo Model
BALB/c mouse are used as recipients and donors in the transplantation. Fifteen diabetic BALB/c mice were randomly divided into 5 groups (3 mice in each group). Then, 250 IEQ islets pretreated with or without bilirubin (20 uM) for 48 h were transplanted into the subrenal site of the diabetic mouse. Ferrin 1 (10 uM) and DFO (10 mM) pretreated islets were also transplanted for comparison. Following, the non-fasting glucose level and bodyweight was the mice were recorded daily.

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Response regulation Bilirubin protects transplanted islets by inhibiting ferroptosis through multiple mechanisms, including ROS scavenging ability, iron-chelating property, and upregulation of Nrf2/HO-1 signaling pathway. Bilirubin could improve islet viability and function through inhibiting ferroptosis, which could be of clinic interest to apply bilirubin into the islet transplantation system. Islet transplantation is an attractive treatment for type 1 diabetic patients.
References
Ref 1 Bilirubin Protects Transplanted Islets by Targeting Ferroptosis. Front Pharmacol. 2020 Jun 16;11:907. doi: 10.3389/fphar.2020.00907. eCollection 2020.