CHEBI:173106 - ferroptocide

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ChEBI Name ferroptocide
ChEBI ID CHEBI:173106
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H36ClN3O7
Net Charge 0
Average Mass 586.080
Monoisotopic Mass 585.22418
InChI InChI=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
InChIKey LLYJISDUHFXOHK-GOCONZMPSA-N
SMILES C[C@@H]1CC[C@@]23C[C@H](O)C(=O)[C@@]2(O)[C@]1(C)[C@@H](C[C@H]([C@@H]3C)C1=CCN2N(C1)C(=O)N(C2=O)C1=CC=CC=C1)OC(=O)CCl
Roles Classification
Biological Role(s): 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.
thioredoxin inhibitor
Any substance which inhibits thioredoxin, a group of small redox proteins.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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
FTC
Note: (2021-05-28) Used as an abbreviation.
 ChEBI
Manual Xref Database
WO2020210158 Patent
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Registry Number Type Source
34613802 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
31086302 PubMed citation Europe PMC
Last Modified
28 May 2021
General Comment
2021-05-28 Relevant articles: https://doi.org/10.1096/fasebj.2021.35.S1.03356