Ferroptosis-centered Drug Response Information

General Information of the Drug (ID: ferrodrug0063)
Name
Microcystin-LR
Synonyms
Microcystin-LR; 101043-37-2; Microcystin LR; Cyanoginosin LR; Toxin-LR; Cyanoginosin-LR; MCYST-LR; Toxin I (Microcystis aeruginosa); Microcystis aeruginosa toxin; CHEBI:6925; Cyanoginosin LA, 5-L-arginine-; CHEMBL444092; C49H74N10O12; EQ8332842Y; NSC-733608; C05371; (5R,8S,11R,12S,15S,18S,19S,22R)-15-[3-(diaminomethylideneamino)propyl]-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-1,5,12,19-tetramethyl-2-methylidene-8-(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid; Akerstox; toxin I, cyanobacterium; Microcystin-a; 1,7-anhydro[D-alanyl-L-leucyl-(3S)-3-methyl-D-beta-aspartyl-L-arginyl-(2S,3S,4E,6E,8S,9S)-3-amino-4,5,6,7-tetradehydro-9-methoxy-2,6,8-trimethyl-10-phenyldecanoyl-D-gamma-glutamyl-2,3-didehydro-N-methylalanine]; cyclo[2,3-didehydro-N-methylalanyl-D-alanyl-L-leucyl-erythro-3-methyl-D-beta-aspartyl-L-arginyl-(2S,3S,4E,6E,8S,9S)-3-amino-4,5,6,7-tetradehydro-9-methoxy-2,6,8-trimethyl-10-phenyldecanoyl-D-gamma-glutamyl]; cyclo[D-alanyl-L-leucyl-(3S)-3-methyl-D-beta-aspartyl-L-arginyl-(2S,3S,4E,6E,8S,9S)-3-amino-4,5,6,7-tetradehydro-9-methoxy-2,6,8-trimethyl-10-phenyldecanoyl-D-gamma-glutamyl-2,3-didehydro-N-methylalanyl]; MCLR; 5-L-Argininecyanoginosin LA; 5-L-Arginine-microcystin LA; cyclo(Ala-Leu-MAsp-Arg-Adda-isoGlu-Mdha); microcystin-la, 5-l-arginine-; UNII-EQ8332842Y; HSDB 7751; toxin t-17 (Microcystis aeruginosa); Toxin T 17 (Microcystis aeruginosa); BRN 4779759; Toxin, blue green alga, Microcystis aeruginosa; Cyanoginosin-LR;MC-LR;Toxin T 17 (Microcystis aeruginosa); MICROCYSTIN-LR [HSDB]; MICROCYSTIN-LR [IARC]; GTPL4735; DTXSID3031654; SCHEMBL21245230; HY-P0072; BDBM50061067; NSC733608; CS-5404; NSC 733608; Q6839436; 1,7-ANHYDRO(D-ALANYL-L-LEUCYL-(3S)-3-METHYL-D-.BETA.-ASPARTYL-L-ARGINYL-(2S,3S,4E,6E,8S,9S)-3-AMINO-4,5,6,7-TETRADEHYDRO-9-METHOXY-2,6,8-TRIMETHYL-10-PHENYLDECANOYL-D-.GAMMA.-GLUTAMYL-2,3-DIDEHYDRO-N-METHYLALANINE); 15-(3-Guanidino-propyl)-8-isobutyl-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenyl-hepta-1,3-dienyl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21heptaaza-cyclopentacosane-11,22-dicarboxylic acid; 15-(3-Guanidino-propyl)-8-isobutyl-18-(6-methoxy-3,5-dimethyl-7-phenyl-hepta-1,3-dienyl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21heptaaza-cyclopentacosane-11,22-dicarboxylic acid; 8-[3-amino(imino)methylaminopropyl]-15-isobutyl-5-[6-methoxy-3,5-dimethyl-7-phenyl-(1E,3E)-1,3-heptadienyl]-4,11,18,22-tetramethyl-21-methylene-3,7,10,14,17,20,23-heptaoxo-2,6,9,13,16,19,22-heptaazacyclopentacosane-1,12-dicarboxylic acid; CYCLO(2,3-DIDEHYDRO-N-METHYLALANYL-D-ALANYL-L-LEUCYL-(3S)-3-METHYL-D-.BETA.-ASPARTYL-L-ARGINYL-(2S,3S,4E,6E,8S,9S)-3-AMINO-9-METHOXY-2,6,8-TRIMETHYL-10-PHENYL-4,6-DECADIENOYL-D-.GAMMA.-GLUTAMYL); CYCLO(2,3-DIDEHYDRO-N-METHYLALANYL-D-ALANYL-L-LEUCYL-ERYTHRO-3-METHYL-D-.BETA.-ASPARTYL-L-ARGINYL-(2S,3S,4E,6E,8S,9S)-4,5,6,7-TETRADEHYDRO-9-METHOXY-2,6,8-TRIMETHYL-10-PHENYL-3-AMINODECANOYL-D-.GAMMA.-GLUTAMYL)

    Click to Show/Hide
Structure
3D MOL
2D MOL
Formula
C49H74N10O12
IUPAC Name
(5R,8S,11R,12S,15S,18S,19S,22R)-15-[3-(diaminomethylideneamino)propyl]-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-1,5,12,19-tetramethyl-2-methylidene-8-(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid
Canonical SMILES
CC1C(NC(=O)C(NC(=O)C(C(NC(=O)C(NC(=O)C(NC(=O)C(=C)N(C(=O)CCC(NC1=O)C(=O)O)C)C)CC(C)C)C(=O)O)C)CCCN=C(N)N)C=CC(=CC(C)C(CC2=CC=CC=C2)OC)C
InChI
InChI=1S/C49H74N10O12/c1-26(2)23-37-46(66)58-40(48(69)70)30(6)42(62)55-35(17-14-22-52-49(50)51)45(65)54-34(19-18-27(3)24-28(4)38(71-10)25-33-15-12-11-13-16-33)29(5)41(61)56-36(47(67)68)20-21-39(60)59(9)32(8)44(64)53-31(7)43(63)57-37/h11-13,15-16,18-19,24,26,28-31,34-38,40H,8,14,17,20-23,25H2,1-7,9-10H3,(H,53,64)(H,54,65)(H,55,62)(H,56,61)(H,57,63)(H,58,66)(H,67,68)(H,69,70)(H4,50,51,52)/b19-18+,27-24+/t28-,29-,30-,31+,34-,35-,36+,37-,38-,40+/m0/s1
InChIKey
ZYZCGGRZINLQBL-GWRQVWKTSA-N
PubChem CID
445434
Full List of Ferroptosis Target Related to This Drug
Unspecific Target
In total 1 item(s) under this Target
Experiment 1 Reporting the Ferroptosis-centered Drug Act on This Target [1]
Responsed Disease Injury of intra-abdominal organs ICD-11: NB91
 Disease Info 
Responsed Regulator Cyclic AMP-dependent transcription factor ATF-4 (ATF4) Driver
 Regulator Info 
Pathway Response Glutathione metabolism hsa00480
Ferroptosis hsa04216
Cell Process Cell ferroptosis
In Vitro Model hLCs (Liver cells)
In Vivo Model
In total, 90 common carp susceptible to MC-LR were obtained from Hulan Fishing Ground (Harbin, China) and acclimatized in 100 L glass aquaria (15 fish per tank) containing continuously aerated water at 23 under a 12 h light-dark cycle for 10 days prior to the experiments. Following acclimation, the fish in MC-LR treatment (M) group (45 fish in 3 tanks) were exposed to 10 ug/L of MC-LR for 15 days. The baseline mean body weights of the fish in the control (C) and M groups were 2.11 ± 0.03 and 2.12 ± 0.01 g, respectively.

    Click to Show/Hide
Response regulation Microcystin-LR induces intestinal injury. Lesion morphological features (vacuolization, deformation and dilation of the endoplasmic reticulum [ER], absence of mitochondrial cristae in mid-intestine), up-regulated mRNA expressions of ER stress (eukaryotic translation initiation factor 2-alpha kinase 3, endoplasmic reticulum to nucleus signaling 1, activating transcription factor [ATF] 6, ATF4, DNA damage-inducible transcript 3), iron accumulation, and down-regulated activity of glutathione peroxidase (GPx) and glutathione (GSH) content were all typical characteristics of ferroptosis in intestinal tissue following MC-LR exposure.
References
Ref 1 Microcystin-LR induces ferroptosis in intestine of common carp (Cyprinus carpio). Ecotoxicol Environ Saf. 2021 Oct 15;223:112610. doi: 10.1016/j.ecoenv.2021.112610. Epub 2021 Aug 5.