Basic information
- CAS
136164-66-4- Standard SMILES
CCCCCCCCC/C(=C\C1=C(C)C(=O)C(OC)=C(OC)C1=O)C(=O)O- InChIKey
AALSSIXXBDPENJ-FYWRMAATSA-N- Molecular formula
- C21H30O6
- Average molar mass
- 378.5 g/mol
- Monoisotopic mass
- 378.20423868
Overview
Erenapurstat is an orally bioavailable inhibitor of apurinic/apyrimidinic endonuclease 1/reduction-oxidation (redox) effector factor-1 (APE1/Ref-1; APEX1), with potential anti-angiogenic and antineoplastic activities. Upon administration, erenapurstat selectively targets and binds to APE1/Ref-1. This inhibits the redox-dependent signaling activity of APE1/Ref-1, by preventing the reduction and activation of numerous APE1/Ref-1-dependent oncogenic transcription factors (TFs), such as nuclear factor kappa B (NF-kB), AP-1, STAT3, p53, NRF2 and HIF-1alpha, that are involved in signaling, cell proliferation, tumor progression and survival of cancer cells. Therefore, this agent inhibits the activation of multiple TF-mediated signaling pathways and inhibits tumor cell proliferation and survival. APE1/Ref-1, a multifunctional protein overexpressed in many cancer cell types, plays a key role as a redox regulator of transcription factor activation and in base excision repair upon DNA damage. It drives cancer cell proliferation, migration, drug resistance, angiogenesis and inflammation and its expression level correlates with increased tumor aggressiveness and decreased patient survival. Erenapurstat specifically blocks the redox activity of APE1/Ref-1 and does not affect its ability to act as a DNA repair endonuclease.
Names & identifiers
- Preferred name
- APE1/Ref-1 Redox Inhibitor APX3330
- IUPAC
- (2E)-2-[(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methylidene]undecanoic acid
- English name
- E 3330
- Molecular formula
- C21H30O6
- Molecular weight
- 378.46
Names & synonyms
Show more names
Database identifiers
- CAS
136164-66-4- PubChem CID
- 6439397
- DTXSID
DTXSID201121926- ChEMBL
CHEMBL578390- UNII
- 11267UI968
- EC Number
- 693-030-4
- Nikkaji
- J529.202F
Properties
Computed structural properties
- XLogP
- 5.3
- Topological polar surface area
- 89.9 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 12
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 666
Physicochemical properties
- Melting point
- 56 · 56-57 °C
- Boiling point
- 542.2 · 542.2±50.0 °C(Predicted)
- Density
- 1.13 · 1.13±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 20 mg/mL · DMSO: >20mg/mL
- form
- powder
- pka
- 4.29 · 4.29±0.19(Predicted)
- color
- red to orange
- InChI
- 1S/C21H30O6/c1-5-6-7-8-9-10-11-12-15(21(24)25)13-16-14(2)17(22)19(26-3)20(27-4)18(16)23/h13H,5-12H2,1-4H3,(H,24,25)/b15-13+
- InChIKey
- AALSSIXXBDPENJ-FYWRMAATSA-N
- SMILES
- CCCCCCCCC\C(=C/C1=C(C)C(=O)C(OC)=C(OC)C1=O)C(O)=O
- FDA UNII
- 11267 UI968 · 11267UI968
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07,GHS09
- Signal word
- Warning
- Hazard statements
- 302 · H302-H411
- Precautionary statements
- 273 · P273-P312-P501
- WGK Germany
- 3 · WGK 3
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 · Aquatic Chronic 4
Safety & regulation
GHS classification
GHS Classification
H413 (100%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]
P273, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS09
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H411
- Hazard Classifications
- Aquatic Chronic 4
- Precautionary statements
- P273-P312-P501
Chemistry & industry
Applications
UsesE 3330 is a potent and selective APE1 inhibitor used in the treatment for age related macular degeneration.
UsesE3330 has been used in the inhibition of endothelial cancer cells and apurinic/apyrimidinic endodeoxyribonuclease 1 (APEX1).
Suppliers43 total
Related reactions
Compound notes
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