Structure via PubChem · Public domain (PubChem)
naphthazarin
Sign in to saveAlso known as 5,8-dihydroxynaphthoquinone, naphthazarone, 5,8-dihydroxy-1,4-naphthalenedione, naphthazarine, 5,8-dihydroxy-1,4-naphthosemiquinone
Naphthazarin, often called 5,8-dihydroxy-1,4-naphthoquinone or 5,8-dihydroxy-1,4-naphthalenedione (IUPAC), is a naturally occurring organic compound with formula , formally derived from 1,4-naphthoquinone through replacement of two hydrogen atoms by hydroxyl (OH) groups. It is thus one of many dihydroxynaphthoquinone structural isomers.
Chemical data
- Formula
- C10H6O4
- Molecular weight
- 190.15 g/mol
- IUPAC name
- 5,8-dihydroxynaphthalene-1,4-dione
- SMILES
- C1=CC(=C2C(=O)C=CC(=O)C2=C1O)O
- InChIKey
- RQNVIKXOOKXAJQ-UHFFFAOYSA-N
- XLogP
- 1.8
- Polar surface area
- 74.6 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
28,735 papers- Fe(III)-Naphthazarin Metal-Phenolic Networks for Glutathione-Depleting Enhanced Ferroptosis-Apoptosis Combined Cancer Therapy.Small (Weinheim an der Bergstrasse, Germany) · 2023
- An overview on the antibacterial properties of juglone, naphthazarin, plumbagin and lawsone derivatives and their metal complexes.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2023
- Stimulation of Suicidal Erythrocyte Death by Naphthazarin.Basic & clinical pharmacology & toxicology · 2015
- The microtubule depolymerizing agent naphthazarin induces both apoptosis and autophagy in A549 lung cancer cells.Apoptosis : an international journal on programmed cell death · 2011
- Naphthazarin Mounted on the Manganese Carbonate Nanocube Induced Enrichment of Endogenous Copper and Fenton-like Reaction for Enhanced Chemodynamic Therapy.ACS applied bio materials · 2025
via PubMed
Wikidata facts
- Mass
- 190.027
Show 4 more facts
- canonical SMILES
- C1=CC(=C2C(=O)C=CC(=O)C2=C1O)O
- chemical formula
- C₁₀H₆O₄
- subject has role
- antineoplastic
- Commons category
- Naphthazarin
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
Naphthazarin, often called 5,8-dihydroxy-1,4-naphthoquinone or 5,8-dihydroxy-1,4-naphthalenedione (IUPAC), is a naturally occurring organic compound with formula , formally derived from 1,4-naphthoquinone through replacement of two hydrogen atoms by hydroxyl (OH) groups. It is thus one of many dihydroxynaphthoquinone structural isomers.
Naphthazarin is soluble in 1,4-dioxane from which it crystallizes as deep red needles that melt at 228−232 °C.
Excerpted from Wikipedia’s “naphthazarin” article, available under the CC BY-SA 4.0 licence.