1,4-Naphthoquinone
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Basic Info
| Common Name | 1,4-Naphthoquinone(F05478) |
| 2D Structure | |
| 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. |
| FRCD ID | F05478 |
| CAS Number | 130-15-4 |
| PubChem CID | 8530 |
| Formula | C10H6O2 |
| IUPAC Name | naphthalene-1,4-dione |
| InChI Key | FRASJONUBLZVQX-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H |
| Canonical SMILES | C1=CC=C2C(=O)C=CC(=O)C2=C1 |
| Isomeric SMILES | C1=CC=C2C(=O)C=CC(=O)C2=C1 |
| Synonyms |
alpha-Naphthoquinone
1,4-NAPHTHOQUINONE
130-15-4
naphthalene-1,4-dione
1,4-Naphthalenedione
p-Naphthoquinone
NAPHTHOQUINONE
1,4-Naphthylquinone
USAF CY-10
1,4-dihydronaphthalene-1,4-dione
|
| Classifies |
Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Naphthalenes |
| Subclass | Naphthoquinones |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Naphthoquinones |
| Alternative Parents | |
| Molecular Framework | Aromatic homopolycyclic compounds |
| Substituents | Naphthoquinone - Aryl ketone - Quinone - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic homopolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as naphthoquinones. These are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 158.156 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Complexity | 227 |
| Monoisotopic Mass | 158.037 |
| Exact Mass | 158.037 |
| XLogP | 1.7 |
| Formal Charge | 0 |
| Heavy Atom Count | 12 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9606 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.8620 |
| P-glycoprotein Substrate | Non-substrate | 0.6646 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6387 |
| Non-inhibitor | 0.8382 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8285 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6497 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7650 |
| CYP450 2D6 Substrate | Non-substrate | 0.9100 |
| CYP450 3A4 Substrate | Non-substrate | 0.6931 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9232 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.8085 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.5518 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.7633 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8310 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.5354 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8962 |
| Non-inhibitor | 0.9243 | |
| AMES Toxicity | AMES toxic | 0.9457 |
| Carcinogens | Non-carcinogens | 0.9182 |
| Fish Toxicity | High FHMT | 0.9120 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9985 |
| Honey Bee Toxicity | High HBT | 0.7678 |
| Biodegradation | Not ready biodegradable | 0.7741 |
| Acute Oral Toxicity | II | 0.7364 |
| Carcinogenicity (Three-class) | Non-required | 0.5631 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.4544 | LogS |
| Caco-2 Permeability | 1.9213 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.8888 | LD50, mol/kg |
| Fish Toxicity | -0.0635 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 2.1846 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Diacetyl/l-Xylulose Reductase Mediates Chemical Redox Cycling in Lung Epithelial Cells. | Chem Res Toxicol | 2017 Jul 17 | 28595002 |
| Antibacterial Activity of Juglone against Staphylococcus aureus: From Apparent toProteomic. | Int J Mol Sci | 2016 Jun 18 | 27322260 |
| 5-O-Acyl plumbagins inhibit DNA polymerase activity and suppress the inflammatory response. | Arch Biochem Biophys | 2015 May 1 | 25748000 |
| Effects of several quinones on insulin aggregation. | Sci Rep | 2014 Jul 10 | 25008537 |
| Ability of the oriental fruit moth Grapholita molesta (Lepidoptera: Tortricidae) to detoxify juglone, the main secondary metabolite of the non-host plant walnut. | J Chem Ecol | 2011 Oct | 21901444 |
| Oxidation of carbaryl in aqueous solution by membrane anodic fenton treatment. | J Agric Food Chem | 2002 Apr 10 | 11929293 |
| Regulation of aflatoxin production by naphthoquinones of walnut (Juglans regia). | J Agric Food Chem | 2000 Sep | 10995372 |
| Differential toxicity of juglone (5-hydroxy-1,4-naphthoquinone) and related naphthoquinones to saturniid moths. | J Chem Ecol | 1994 Jul | 24242656 |
Targets
- 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
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 ]
- 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
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 ]
- 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
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 ]
- 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 ]
- 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
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 ]