ContaminantDB: 1,4-Naphthoquinone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (5)XML

Record Information

Version

1.0

Creation Date

2014-09-08 02:39:04 UTC

Update Date

2026-04-16 22:40:25 UTC

Accession Number

CHEM003597

Identification

Common Name

1,4-Naphthoquinone

Class

Small Molecule

Description

1,4-Naphthoquinone or para-naphthoquinone is an organic compound derived from naphthalene. Several isomeric naphthoquinones are known, notably 1,2-naphthoquinone. 1,4-Naphthoquinone forms volatile yellow triclinic crystals and has a sharp odor similar to benzoquinone. It is almost insoluble in cold water, slightly soluble in petroleum ether, and more soluble in polar organic solvents. In alkaline solutions it produces a reddish-brown color. Vitamin K is a derivative of 1,4-naphthoquinone. It is a planar molecule with one aromatic ring fused to a quinone subunit. Naphthalene is a constituent of jet fuel, diesel fuel and cigarette smoke. It is also a byproduct of incomplete combustion and hence is an ubiquitous environmental pollutant. The typical air concentration of naphthalene in cities is about 0.18 ppb.

Contaminant Sources

Clean Air Act Chemicals
FooDB Chemicals
HPV EPA Chemicals
T3DB toxins
Tobacco Smoke Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Cigarette Toxin
Ester
Food Toxin
Fuel
Industrial/Workplace Toxin
Organic Compound
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,4-Dihydro-1,4-diketonaphthalene	ChEBI
1,4-Naphthalenedione	ChEBI
1,4-NQ	ChEBI
[1,4]Naphthoquinon	ChEBI
alpha-Naphthoquinone	ChEBI
Naphthoquinone	ChEBI
p-Naphthoquinone	ChEBI
a-Naphthoquinone	Generator
Α-naphthoquinone	Generator
Succivil	MeSH

Chemical Formula

C₁₀H₆O₂

Average Molecular Mass

158.153 g/mol

Monoisotopic Mass

158.037 g/mol

CAS Registry Number

130-15-4

IUPAC Name

1,4-dihydronaphthalene-1,4-dione

Traditional Name

naphthoquinone

SMILES

O=C1C=CC(=O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H

InChI Key

FRASJONUBLZVQX-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Aryl ketone
Quinone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthoquinone (CHEBI:27418 )
a small molecule (CPD0-954 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Actin Filament
Cell junction
Cell surface
Cytoplasm
Cytoplasmic vesicle
Cytoskeleton
Cytosol
Endoplasmic reticulum
Extracellular
Extracellular matrix
Intermediate Filament
Lysosome
Membrane Fraction
Microsome
Microtubule
Mitochondrial Membrane
Mitochondrion
Peroxisome
Plasma Membrane
Ribosome
Sarcoplasmic Reticulum
Soluble Fraction
Tubulin

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Apoptosis	Not Available	map04210
Cell cycle	Not Available	map04110
Antiviral Agents	Not Available	Not Available
Oxidative phosphorylation	Not Available	map00190
Endocytosis	Not Available	map04144
Metabolic Pathways	Not Available	Not Available
Naphthalene Degradation	Not Available	Not Available
Fanconi anemia pathway	Not Available	map03460
Two Component System	Not Available	Not Available
Renin-angiotensin system	Not Available	map04614
Quinolines	Not Available	Not Available
Proteasome	Not Available	Not Available
N-glycan biosynthesis	Not Available	map00510
Homologous recombination	Not Available	map03440
Fatty Acid Degradation	Not Available	Not Available
Arachidonic Acid Metabolism	SMP00075	map00590
Antifungal Agents	Not Available	Not Available
Aflatoxin Biosynthesis	Not Available	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	126°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.83 g/L	ALOGPS
logP	1.61	ALOGPS
logP	1.49	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	46.18 m³·mol⁻¹	ChemAxon
Polarizability	15.43 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-1900000000-c1d8a7cd50dab2243638	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-c91d1d0c196a75db8099	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-7023e1d6ad6bb601f4af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9800000000-704e8571b85c1e233d67	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-8ab4a16729cf8089e223	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-8ab4a16729cf8089e223	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-2900000000-6c220c84a505df1ccf10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-6d3211f5b01d2864ea9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-2f0324ec6d5eecc4a333	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9800000000-2c096a2117fab889955c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-3f5765b536b8e874a7de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-3f5765b536b8e874a7de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-6900000000-dee23989cd0e111e875b	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0zi0-4900000000-aff14fc4ebdec6f27f11	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is a toxic chemical found in cigarettes or generated by tobacco combustion.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0244221

FooDB ID

FDB000340

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

8215

ChEBI ID

27418

PubChem Compound ID

Not Available

Kegg Compound ID

C02617

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=26684482

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217

1,4-Naphthoquinone (CHEM003597)

Structure for CHEM003597: 1,4-Naphthoquinone