T3DB: 1,4-Naphthoquinone

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

Targets (5)

Record Information

Version

2.0

Creation Date

2014-09-08 02:39:04 UTC

Update Date

2014-12-24 20:26:54 UTC

Accession Number

T3D4637

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.

Compound Type

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

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
1,4-dihydro-1,4-Diketonaphthalene
1,4-Naphthalenedione
alpha-Naphthoquinone
Naphthoquinone
P-Naphthoquinone

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

InChIKey=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
LogP	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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-1900000000-c1d8a7cd50dab2243638	2021-09-24	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-c91d1d0c196a75db8099	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-7023e1d6ad6bb601f4af	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9800000000-704e8571b85c1e233d67	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-8ab4a16729cf8089e223	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-8ab4a16729cf8089e223	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-2900000000-6c220c84a505df1ccf10	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-6d3211f5b01d2864ea9b	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-2f0324ec6d5eecc4a333	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9800000000-2c096a2117fab889955c	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-3f5765b536b8e874a7de	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-3f5765b536b8e874a7de	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-6900000000-dee23989cd0e111e875b	2021-10-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0zi0-4900000000-aff14fc4ebdec6f27f11	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View 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

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

27418

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

T3D4637.pdf

General References

Waidyanatha S, Rappaport SM: Hemoglobin and albumin adducts of naphthalene-1,2-oxide, 1,2-naphthoquinone and 1,4-naphthoquinone in Swiss Webster mice. Chem Biol Interact. 2008 Mar 27;172(2):105-14. doi: 10.1016/j.cbi.2008.01.004. Epub 2008 Jan 16. [18291356 ]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Amine oxidase [flavin-containing] A

General Function:: Serotonin binding
Specific Function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular Weight:: 59681.27 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
Inhibitory	7.7 uM	Not Available	BindingDB 24776

References

Coelho Cerqueira E, Netz PA, Diniz C, Petry do Canto V, Follmer C: Molecular insights into human monoamine oxidase (MAO) inhibition by 1,4-naphthoquinone: evidences for menadione (vitamin K3) acting as a competitive and reversible inhibitor of MAO. Bioorg Med Chem. 2011 Dec 15;19(24):7416-24. doi: 10.1016/j.bmc.2011.10.049. Epub 2011 Oct 20. [22071524 ]

Target Details

2. Amine oxidase [flavin-containing] B

General Function:: Primary amine oxidase activity
Specific Function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular Weight:: 58762.475 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
Inhibitory	1.5 uM	Not Available	BindingDB 24776

References

Coelho Cerqueira E, Netz PA, Diniz C, Petry do Canto V, Follmer C: Molecular insights into human monoamine oxidase (MAO) inhibition by 1,4-naphthoquinone: evidences for menadione (vitamin K3) acting as a competitive and reversible inhibitor of MAO. Bioorg Med Chem. 2011 Dec 15;19(24):7416-24. doi: 10.1016/j.bmc.2011.10.049. Epub 2011 Oct 20. [22071524 ]

Target Details

3. DNA topoisomerase 2-alpha

General Function:: Ubiquitin binding
Specific Function:: Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Essential during mitosis and meiosis for proper segregation of daughter chromosomes. May play a role in regulating the period length of ARNTL/BMAL1 transcriptional oscillation (By similarity).
Gene Name:: TOP2A
Uniprot ID:: P11388
Molecular Weight:: 174383.88 Da

References

Gurbani D, Kukshal V, Laubenthal J, Kumar A, Pandey A, Tripathi S, Arora A, Jain SK, Ramachandran R, Anderson D, Dhawan A: Mechanism of inhibition of the ATPase domain of human topoisomerase IIalpha by 1,4-benzoquinone, 1,2-naphthoquinone, 1,4-naphthoquinone, and 9,10-phenanthroquinone. Toxicol Sci. 2012 Apr;126(2):372-90. doi: 10.1093/toxsci/kfr345. Epub 2012 Jan 4. [22218491 ]

Target Details

4. Dual specificity mitogen-activated protein kinase kinase 1

General Function:: Receptor signaling protein tyrosine phosphatase activity
Specific Function:: Dual specificity protein kinase which acts as an essential component of the MAP kinase signal transduction pathway. Binding of extracellular ligands such as growth factors, cytokines and hormones to their cell-surface receptors activates RAS and this initiates RAF1 activation. RAF1 then further activates the dual-specificity protein kinases MAP2K1/MEK1 and MAP2K2/MEK2. Both MAP2K1/MEK1 and MAP2K2/MEK2 function specifically in the MAPK/ERK cascade, and catalyze the concomitant phosphorylation of a threonine and a tyrosine residue in a Thr-Glu-Tyr sequence located in the extracellular signal-regulated kinases MAPK3/ERK1 and MAPK1/ERK2, leading to their activation and further transduction of the signal within the MAPK/ERK cascade. Depending on the cellular context, this pathway mediates diverse biological functions such as cell growth, adhesion, survival and differentiation, predominantly through the regulation of transcription, metabolism and cytoskeletal rearrangements. One target of the MAPK/ERK cascade is peroxisome proliferator-activated receptor gamma (PPARG), a nuclear receptor that promotes differentiation and apoptosis. MAP2K1/MEK1 has been shown to export PPARG from the nucleus. The MAPK/ERK cascade is also involved in the regulation of endosomal dynamics, including lysosome processing and endosome cycling through the perinuclear recycling compartment (PNRC), as well as in the fragmentation of the Golgi apparatus during mitosis.
Gene Name:: MAP2K1
Uniprot ID:: Q02750
Molecular Weight:: 43438.65 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
IC50	0.38 uM	Not Available	BindingDB 24776

References

Fedorov O, Marsden B, Pogacic V, Rellos P, Muller S, Bullock AN, Schwaller J, Sundstrom M, Knapp S: A systematic interaction map of validated kinase inhibitors with Ser/Thr kinases. Proc Natl Acad Sci U S A. 2007 Dec 18;104(51):20523-8. Epub 2007 Dec 11. [18077363 ]

Target Details

5. M-phase inducer phosphatase 2

General Function:: Protein tyrosine phosphatase activity
Specific Function:: Tyrosine protein phosphatase which functions as a dosage-dependent inducer of mitotic progression. Required for G2/M phases of the cell cycle progression and abscission during cytokinesis in a ECT2-dependent manner. Directly dephosphorylates CDK1 and stimulates its kinase activity. The three isoforms seem to have a different level of activity.
Gene Name:: CDC25B
Uniprot ID:: P30305
Molecular Weight:: 64986.745 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
IC50	2.76 uM	Not Available	BindingDB 24776

References

Cao S, Murphy BT, Foster C, Lazo JS, Kingston DG: Bioactivities of simplified adociaquinone B and naphthoquinone derivatives against Cdc25B, MKP-1, and MKP-3 phosphatases. Bioorg Med Chem. 2009 Mar 15;17(6):2276-81. doi: 10.1016/j.bmc.2008.10.090. Epub 2008 Nov 8. [19028102 ]

1,4-Naphthoquinone (T3D4637)

Structure for T3D4637: 1,4-Naphthoquinone

Targets

Binding/Activity Constants

References

Binding/Activity Constants

References

References

Binding/Activity Constants

References

Binding/Activity Constants

References