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Gamitrinib TPP

CAT: 0804-HY-102007Size: 1 EachDry Ice: NoHazardous: No
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Description
Gamitrinib TPP is a Gamitrinib (GA) mitochondrial matrix inhibitor. Gamitrinib TPP is a mitochondrial targeted HSP90 inhibitor with anti-cancer activity.
CAS Number
1131626-46-4
UNSPSC
12352005
Target
HSP
Type
Reference compound
Related Pathways
Cell Cycle/DNA Damage; Metabolic Enzyme/Protease
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/Gamitrinib_TPP.html
Solubility
10 mM in DMSO
Smiles
O=C(C=C1NC(/C(C)=C/C=C/[C@H](OC)[C@@H](OC(N)=O)/C(C)=C/[C@H](C)[C@H]2O)=O)C(NCCCCCC[P+](C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)=C(C[C@H](C[C@@H]2OC)C)C1=O
Molecular Formula
C52H65N3O8P
Molecular Weight
891.06
References & Citations
[1]Markus D. Siegelin, et al. Exploiting the mitochondrial unfolded protein response for cancer therapy in mice and human cells. J Clin Invest. 2011 Apr 1; 121 (4) : 1349–1360.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
No Development Reported
Isoform
HSP90
Citation 01
Cancer Lett. 2025 Aug 9:632:217977.|Exp Ther Med. 2021 Nov;22 (5) :1246.|bioRxiv. 2024 Jan 2.|bioRxiv. 2024 September 03.|Cancer Lett. 2022 Nov 28:549:215915.|Clin Cancer Res. 2022 May 13;28 (10) :2180-2195.|Elife. 2021 Jun 16:10:e63104.|Front Biosci (Landmark Ed) . 2023 Sep 26;28 (9) :227.|J Invest Dermatol. 2025 Feb 18:S0022-202X (25) 00110-1.|Nature. 2020 Mar;579 (7799) :433-437. |Research Square Preprint. 2020 Sep.|Sci Adv. 2025 Oct 24;11 (43) :eadw6064.|SSRN. 2023 Jul 11.

Chemical Information

Gamitrinib

Gamitrinib is a resorcinolic-based mitochondrial-targeted heat shock protein 90 (Hsp90) family inhibitor, with potential antineoplastic activity. Upon administration, gamitrinib targets and inhibits the activity of Hsp90 heat shock proteins, such as TNF receptor-associated protein-1 (TRAP1). This induces the accumulation of the mitochondrial kinase PINK1 and the cytosolic E3 ubiquitin (Ub) ligase Parkin, ubiquitylates substrate proteins, and induces PINK1/Parkin-dependent mitophagy. Gamitrinib induces acute mitochondrial dysfunction, loss of membrane potential and membrane rupture leading to the induction of apoptosis in susceptible tumor cells. Hsp90, a chaperone complex protein upregulated in a variety of tumor cell types, regulates the folding and degradation of many oncogenic signaling proteins.

CAS Number1131626-46-4
PubChem CID25232582
IUPAC Name6-[[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-9-carbamoyloxy-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-19-yl]amino]hexyl-triphenylphosphanium
Molecular FormulaC52H65N3O8P+
Molecular Weight891.1
XLogP7.8
Topological Polar Surface Area166
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count9
Rotatable Bond Count15
Heavy Atom Count64
Formal Charge1
Complexity1690
SMILES
C[C@H]1C[C@@H]([C@@H]([C@H](/C=C(/[C@@H]([C@H](/C=C\C=C(\C(=O)NC2=CC(=O)C(=C(C1)C2=O)NCCCCCC[P+](C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)/C)OC)OC(=O)N)\C)C)O)OC
InChI
InChI=1S/C52H64N3O8P/c1-35-31-42-47(54-29-18-7-8-19-30-64(39-22-12-9-13-23-39,40-24-14-10-15-25-40)41-26-16-11-17-27-41)44(56)34-43(49(42)58)55-51(59)36(2)21-20-28-45(61-5)50(63-52(53)60)38(4)33-37(3)48(57)46(32-35)62-6/h9-17,20-28,33-35,37,45-46,48,50,57H,7-8,18-19,29-32H2,1-6H3,(H3-,53,54,55,56,58,59,60)/p+1/b28-20-,36-21+,38-33+/t35-,37+,45+,46+,48-,50+/m1/s1
InChIKey
OAUJLFPWRFHSNE-FEHIUCOBSA-O
Chemical Structure
2D Structure
2D structure of Gamitrinib
CAS: 1131626-46-4
CID: 25232582
Formula: C52H65N3O8P+
MW: 891.1
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight891.1
XLogP37.8
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count9
Rotatable Bond Count15
Exact Mass890.45092804
Monoisotopic Mass890.45092804
Topological Polar Surface Area166 Ų
Heavy Atom Count64
Formal Charge1
Complexity1690
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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