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CHEBI:173106 - ferroptocide

ChEBI IDCHEBI:173106
ChEBI Nameferroptocide
Stars
DefinitionA triazolopyridazine that is 5,8-dihydro-1H-[1,2,4]triazolo[1,2-a]pyridazine-1,3(2H)-dione substituted by phenyl and (2S,3aS,4S,5S,7R,8S,8aS,9R)-7-[(chloroacetyl)oxy]-2,8a-dihydroxy-4,8,9-trimethyl-1-oxooctahydro-1H-3a,8-propanoazulen-5-yl groups at positions 2 and 6, respectively. It is a small molecule inhibitor of thioredoxin, a key component of the antioxidant system in cells. It induces rapid ferroptotic death in immortalized cancer cell lines and primary cancer cells from patients.
Last Modified28 May 2021
SubmitterAdnan
DownloadsMolfile
FormulaC30H36ClN3O7
Net Charge0
Average Mass586.085
Monoisotopic Mass585.22418
SMILESC[C@@H]1CC[C@@]23C[C@H](O)C(=O)[C@@]2(O)[C@]1(C)[C@H](OC(=O)CCl)C[C@@H](C1=CCn2c(=O)n(-c4ccccc4)c(=O)n2C1)[C@@H]3C
InChIInChI=1S/C30H36ClN3O7/c1-17-9-11-29-14-22(35)25(37)30(29,40)28(17,3)23(41-24(36)15-31)13-21(18(29)2)19-10-12-32-26(38)34(27(39)33(32)16-19)20-7-5-4-6-8-20/h4-8,10,17-18,21-23,35,40H,9,11-16H2,1-3H3/t17-,18+,21-,22+,23-,28+,29+,30-/m1/s1
InChIKeyLLYJISDUHFXOHK-GOCONZMPSA-N
Roles Classification
Biological Roles:
thioredoxin inhibitor  Any substance which inhibits thioredoxin, a group of small redox proteins.
ferroptosis inducer  Any substance that induces or promotes ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
ferroptocide (CHEBI:173106) has role antineoplastic agent (CHEBI:35610)
ferroptocide (CHEBI:173106) has role ferroptosis inducer (CHEBI:173085)
ferroptocide (CHEBI:173106) has role thioredoxin inhibitor (CHEBI:173108)
ferroptocide (CHEBI:173106) is a benzenes (CHEBI:22712)
ferroptocide (CHEBI:173106) is a carbotricyclic compound (CHEBI:38032)
ferroptocide (CHEBI:173106) is a carboxylic ester (CHEBI:33308)
ferroptocide (CHEBI:173106) is a cyclic ketone (CHEBI:3992)
ferroptocide (CHEBI:173106) is a organochlorine compound (CHEBI:36683)
ferroptocide (CHEBI:173106) is a secondary alcohol (CHEBI:35681)
ferroptocide (CHEBI:173106) is a tertiary alcohol (CHEBI:26878)
ferroptocide (CHEBI:173106) is a triazolopyridazine (CHEBI:48384)
IUPAC Name 
(2S,3aS,4S,5R,7R,8S,8aS,9R)-5-(1,3-dioxo-2-phenyl-2,3,5,8-tetrahydro-1H-[1,2,4]triazolo[1,2-a]pyridazin-6-yl)-2,8a-dihydroxy-4,8,9-trimethyl-1-oxooctahydro-1H-3a,8-propanoazulen-7-yl chloroacetate
Synonym  Source
FTCChEBI
Manual XrefsDatabases
WO2020210158Patent
Registry NumbersSources
Reaxys:34613802Reaxys
Citations