naphthalene (CHEBI:16482)

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CHEBI:16482 - naphthalene

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ChEBI Name	naphthalene

ChEBI ID	CHEBI:16482

Definition	An aromatic hydrocarbon comprising two fused benzene rings. It occurs in the essential oils of numerous plant species e.g. magnolia.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:44619, CHEBI:7472, CHEBI:14638, CHEBI:25469

Supplier Information	ChemicalBook:CB2472212, eMolecules:26755049, eMolecules:482250, ZINC000000967522

Download	Molfile XML SDF

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1.8188 -1.5937 0.0059 C 0 0 0 0 0 0 0 0 0 0 0 0

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5.7541 -4.6657 0.1740 C 0 0 0 0 0 0 0 0 0 0 0 0

4.6337 -5.4793 0.1102 C 0 0 0 0 0 0 0 0 0 0 0 0

3.3686 -4.9161 0.0524 C 0 0 0 0 0 0 0 0 0 0 0 0

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1.9605 -2.9723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0

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4.7496 -6.5843 0.1053 H 0 0 0 0 0 0 0 0 0 0 0 0

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Wikipedia	License
Naphthalene is an organic compound with formula C10H8. It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings. It is the main ingredient of traditional mothballs.
Read full article at Wikipedia

Formula

C10H8

Net Charge

Average Mass

128.17052

Monoisotopic Mass

128.06260

InChI

InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H

InChIKey

UFWIBTONFRDIAS-UHFFFAOYSA-N

SMILES

c1ccc2ccccc2c1

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Gallus gallus (NCBI:txid9031)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Chemical Role(s):	environmental contaminant Any minor or unwanted substance introduced into the environment that can have undesired effects.

Biological Role(s):	volatile oil component Any plant metabolite that is found naturally as a component of a volatile oil. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. carcinogenic agent A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities. (via polycyclic arene ) apoptosis inhibitor Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

Application(s):	endocrine disruptor Any compound that can disrupt the functions of the endocrine (hormone) system (via polycyclic arene )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	naphthalene (CHEBI:16482) has role apoptosis inhibitor (CHEBI:68494) naphthalene (CHEBI:16482) has role carcinogenic agent (CHEBI:50903) naphthalene (CHEBI:16482) has role environmental contaminant (CHEBI:78298) naphthalene (CHEBI:16482) has role mouse metabolite (CHEBI:75771) naphthalene (CHEBI:16482) has role plant metabolite (CHEBI:76924) naphthalene (CHEBI:16482) has role volatile oil component (CHEBI:27311) naphthalene (CHEBI:16482) is a ortho-fused bicyclic arene (CHEBI:35426) naphthalene (CHEBI:16482) is a naphthalenes (CHEBI:25477)

Incoming	1,2-naphthoquinone (CHEBI:34055) has parent hydride naphthalene (CHEBI:16482) 1,4-naphthoquinone (CHEBI:27418) has parent hydride naphthalene (CHEBI:16482) 1-naphthyl isothiocyanate (CHEBI:35455) has parent hydride naphthalene (CHEBI:16482) chlorinated naphthalene (CHEBI:156062) has parent hydride naphthalene (CHEBI:16482) dimethylnaphthalene (CHEBI:48853) has parent hydride naphthalene (CHEBI:16482) methylnaphthalene (CHEBI:50715) has parent hydride naphthalene (CHEBI:16482) naphthalene 1,2-oxide (CHEBI:52431) has parent hydride naphthalene (CHEBI:16482) naphthalene-2,6-dicarboxylic acid (CHEBI:44460) has parent hydride naphthalene (CHEBI:16482) naphthol (CHEBI:35682) has parent hydride naphthalene (CHEBI:16482) naphthylacetic acid (CHEBI:35629) has parent hydride naphthalene (CHEBI:16482) nitronaphthalene (CHEBI:50631) has parent hydride naphthalene (CHEBI:16482) tetralin (CHEBI:35008) has parent hydride naphthalene (CHEBI:16482)

IUPAC Name

naphthalene

Synonyms	Sources
naftaleno	ChEBI
naftalina	ChEBI
naphtalène	ChEBI
naphtaline	ChEBI
Naphthalen	ChEBI
Naphthalene	KEGG COMPOUND
NAPHTHALENE	PDBeChem
naphthalene	UniProt
Naphthalin	NIST Chemistry WebBook

Manual Xrefs	Databases
1312	PPDB
C00001259	KNApSAcK
C00829	KEGG COMPOUND
c0333	UM-BBD
HMDB0029751	HMDB
Naphthalene	Wikipedia
NAPHTHALENE	MetaCyc
NPY	PDBeChem
View more database links

Registry Numbers	Types	Sources
1421310	Reaxys Registry Number	Reaxys
3347	Gmelin Registry Number	Gmelin
91-20-3	CAS Registry Number	KEGG COMPOUND
91-20-3	CAS Registry Number	NIST Chemistry WebBook
91-20-3	CAS Registry Number	ChemIDplus

Citations

Mijaylova Nacheva P, Esquivel Sotelo A (2016)
Removal of naphthalene and phenanthrene using aerobic membrane bioreactor.
Biodegradation 27, 83-93 [PubMed:26895256]
[show Abstract]

Hewage D, Silva WR, Cao W, Yang DS (2016)
La-Activated Bicyclo-oligomerization of Acetylene to Naphthalene.
Journal of the American Chemical Society 138, 2468-2471 [PubMed:26875834]
[show Abstract]

Jaleta KT, Hill SR, Birgersson G, Tekie H, Ignell R (2016)
Chicken volatiles repel host-seeking malaria mosquitoes.
Malaria journal 15, 354 [PubMed:27439360]
[show Abstract]

Background

Anopheles arabiensis is a dominant vector of malaria in sub-Saharan Africa, which feeds indoors and outdoors on human and other vertebrate hosts, making it a difficult species to control with existing control methods. Novel methods that reduce human-vector interactions are, therefore, required to improve the impact of vector control programmes. Investigating the mechanisms underlying the host discrimination process in An. arabiensis could provide valuable knowledge leading to the development of novel control technologies. In this study, a host census and blood meal analysis were conducted to determine the host selection behaviour of An. arabiensis. Since mosquitoes select and discriminate among hosts primarily using olfaction, the volatile headspace of the preferred non-human host and non-host species, were collected. Using combined gas chromatography and electroantennographic detection analysis followed by combined gas chromatography and mass spectrometry, the bioactive compounds in the headspace collections were identified. The efficiency of the identified non-host compounds to repel host-seeking malaria mosquitoes was tested under field conditions.

Results

The host census and blood meal analyses demonstrated that An. arabiensis strongly prefers human blood when host seeking indoors, while it randomly feeds on cattle, goats and sheep when found outdoors. However, An. arabiensis avoids chickens despite their relatively high abundance, indicating that chickens are a non-host species for this vector. Eleven bioactive compounds were found in the headspace of the non-host species. Six of these were species-specific, out of which four were identified using combined gas chromatography and mass spectrometry. When tested in the field, the chicken-specific compounds, isobutyl butyrate, naphthalene, hexadecane and trans-limonene oxide, and the generic host compounds, limonene, cis-limonene oxide and β-myrcene, significantly reduced trap catches within the house compared to a negative control. A significant reduction in trap catch was also observed when suspending a caged chicken next to the trap.

Conclusions

Non-host volatiles repel host-seeking An. arabiensis and thus play a significant role in host discrimination. As such, this study demonstrates that non-host volatiles can provide protection to humans at risk of mosquito-vectored diseases in combination with established control programmes.

Krång AS (2007)
Naphthalene disrupts pheromone induced mate search in the amphipod Corophium volutator (Pallas).
Aquatic toxicology (Amsterdam, Netherlands) 85, 9-18 [PubMed:17850896]
[show Abstract]

Kokel D, Li Y, Qin J, Xue D (2006)
The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans.
Nature chemical biology 2, 338-345 [PubMed:16699520]
[show Abstract]

Voets M, Antes I, Scherer C, Müller-Vieira U, Biemel K, Barassin C, Marchais-Oberwinkler S, Hartmann RW (2005)
Heteroaryl-substituted naphthalenes and structurally modified derivatives: selective inhibitors of CYP11B2 for the treatment of congestive heart failure and myocardial fibrosis.
Journal of medicinal chemistry 48, 6632-6642 [PubMed:16220979]
[show Abstract]

Xing B (2001)
Sorption of naphthalene and phenanthrene by soil humic acids.
Environmental pollution (Barking, Essex : 1987) 111, 303-309 [PubMed:11202734]
[show Abstract]

Pandya U, Saini MK, Jin GF, Awasthi S, Godley BF, Awasthi YC (2000)
Dietary curcumin prevents ocular toxicity of naphthalene in rats.
Toxicology letters 115, 195-204 [PubMed:10814889]
[show Abstract]

Last Modified

06 July 2020

CHEBI:16482 - naphthalene

Background

Results

Conclusions

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