APE1/Ref-1 Redox Inhibitor APX3330

HCID 6439397

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

E3330136164-66-4E 3330E-3330APX-3330APX333011267UI968APX 3330(2E)-3-(5-(2,3-Dimethoxy-6-methyl-1,4-benzoquinoyl))-2-nonyl-2-propenoic acidAPE1/REF-1 REDOX INHIBITOR APX3330(2E)-2-[(4,5-Dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)methylene]undecanoic acidUndecanoic acid, 2-((4,5-dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)methylene)-, (E)-
Show more names
CS-1756APX-3330 ,S7445E3330 (APX-3330)E3330, 10 mM in DMSO(E)-2-((4,5-Dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methylene)undecanoic acid
((2E)-2-((4,5-dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)methylene)-undecanoic Acid(2E)-2-((4,5-Dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)methylene)undecanoic acid[(2E)-2-[(4,5-dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)methylene]-undecanoic AcidUNDECANOIC ACID, 2-((4,5-DIMETHOXY-2-METHYL-3,6-DIOXO-1,4-CYCLOHEXADIEN-1-YL)METHYLENE)-, (2E)-Undecanoic acid, 2-[(4,5-dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)methylene]-, (2E)-RefChem:558393APE1/Ref-1 Inhibitor APX3330(2E)-2-[(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methylidene]undecanoic acid

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

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

Safety & regulation

GHS classification

GHS Classification · 3 items

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

Hazard Classes and CategoriesAquatic Chronic 4 (100%)

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

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

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
江苏艾康生物医药研发有限公司025-5885952 15955137747 · [email protected]

Related reactions

2 records

Compound notes

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