1,2-Naphthoquinone
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Basic Info
| Common Name | 1,2-Naphthoquinone(F05477) |
| 2D Structure | |
| Description | 1,2-Naphthoquinone or ortho-naphthoquinone is a polycyclic aromatic organic compound with formula C10H6O2. This double ketone (quinone) is a reactive metabolite of naphthalene and is found in diesel exhaust particles. The accumulation of this toxic metabolite in rats from doses of naphthalene has been shown to cause eye damage, including the formation of cataracts. 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 | F05477 |
| CAS Number | 524-42-5 |
| PubChem CID | 10667 |
| Formula | C10H6O2 |
| IUPAC Name | naphthalene-1,2-dione |
| InChI Key | KETQAJRQOHHATG-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H |
| Canonical SMILES | C1=CC=C2C(=C1)C=CC(=O)C2=O |
| Isomeric SMILES | C1=CC=C2C(=C1)C=CC(=O)C2=O |
| Synonyms |
.beta.-Naphthoquinone
1,2-NAPHTHOQUINONE
524-42-5
1,2-Naphthalenedione
naphthalene-1,2-dione
o-Naphthoquinone
beta-Naphthoquinone
1,2-Naphthaquinone
1,2-Naftochinon
1,2-Naftochinon [Czech]
|
| 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 - Cyclic ketone - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - 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 | 253 |
| Monoisotopic Mass | 158.037 |
| Exact Mass | 158.037 |
| XLogP | 1.5 |
| 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+ | 0.9569 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.8218 |
| P-glycoprotein Substrate | Non-substrate | 0.6626 |
| P-glycoprotein Inhibitor | Inhibitor | 0.6346 |
| Non-inhibitor | 0.7559 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8384 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7042 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7774 |
| CYP450 2D6 Substrate | Non-substrate | 0.8948 |
| CYP450 3A4 Substrate | Non-substrate | 0.6537 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9061 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.8150 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.5770 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.6630 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8436 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.5999 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9319 |
| Non-inhibitor | 0.8994 | |
| AMES Toxicity | AMES toxic | 0.9108 |
| Carcinogens | Non-carcinogens | 0.9254 |
| Fish Toxicity | High FHMT | 0.9462 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9978 |
| Honey Bee Toxicity | High HBT | 0.7243 |
| Biodegradation | Not ready biodegradable | 0.8648 |
| Acute Oral Toxicity | II | 0.5817 |
| Carcinogenicity (Three-class) | Non-required | 0.5254 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.3519 | LogS |
| Caco-2 Permeability | 1.8495 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.6376 | LD50, mol/kg |
| Fish Toxicity | -0.1454 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.2250 | pIGC50, ug/L |
Targets
- General Function:
- Methylumbelliferyl-acetate deacetylase activity
- Specific Function:
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
- Gene Name:
- CES2
- Uniprot ID:
- O00748
- Molecular Weight:
- 61806.41 Da
References
- Hyatt JL, Wadkins RM, Tsurkan L, Hicks LD, Hatfield MJ, Edwards CC, Ross CR 2nd, Cantalupo SA, Crundwell G, Danks MK, Guy RK, Potter PM: Planarity and constraint of the carbonyl groups in 1,2-diones are determinants for selective inhibition of human carboxylesterase 1. J Med Chem. 2007 Nov 15;50(23):5727-34. Epub 2007 Oct 17. [17941623 ]
- 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:
- Protein tyrosine/threonine phosphatase activity
- Specific Function:
- Dual specificity phosphatase that dephosphorylates MAP kinase MAPK1/ERK2 on both 'Thr-183' and 'Tyr-185', regulating its activity during the meiotic cell cycle.
- Gene Name:
- DUSP1
- Uniprot ID:
- P28562
- Molecular Weight:
- 39297.37 Da
References
- Liu T, Lin Y, Wen X, Jorissen RN, Gilson MK: BindingDB: a web-accessible database of experimentally determined protein-ligand binding affinities. Nucleic Acids Res. 2007 Jan;35(Database issue):D198-201. Epub 2006 Dec 1. [17145705 ]
- General Function:
- Ubiquitin protein ligase binding
- Specific Function:
- Involved in redox regulation of the cell. Can reduce H(2)O(2) and short chain organic, fatty acid, and phospholipid hydroperoxides. May play a role in the regulation of phospholipid turnover as well as in protection against oxidative injury.
- Gene Name:
- PRDX6
- Uniprot ID:
- P30041
- Molecular Weight:
- 25034.715 Da
References
- Takayama N, Iwamoto N, Sumi D, Shinkai Y, Tanaka-Kagawa T, Jinno H, Kumagai Y: Peroxiredoxin 6 is a molecular target for 1,2-naphthoquinone, an atmospheric electrophile, in human pulmonary epithelial A549 cells. J Toxicol Sci. 2011;36(6):817-21. [22129745 ]
- General Function:
- Transmembrane receptor protein tyrosine phosphatase activity
- Specific Function:
- Protein tyrosine-protein phosphatase required for T-cell activation through the antigen receptor. Acts as a positive regulator of T-cell coactivation upon binding to DPP4. The first PTPase domain has enzymatic activity, while the second one seems to affect the substrate specificity of the first one. Upon T-cell activation, recruits and dephosphorylates SKAP1 and FYN. Dephosphorylates LYN, and thereby modulates LYN activity (By similarity).
- Gene Name:
- PTPRC
- Uniprot ID:
- P08575
- Molecular Weight:
- 147253.075 Da
References
- Urbanek RA, Suchard SJ, Steelman GB, Knappenberger KS, Sygowski LA, Veale CA, Chapdelaine MJ: Potent reversible inhibitors of the protein tyrosine phosphatase CD45. J Med Chem. 2001 May 24;44(11):1777-93. [11356112 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Tyrosine-protein phosphatase which acts as a regulator of endoplasmic reticulum unfolded protein response. Mediates dephosphorylation of EIF2AK3/PERK; inactivating the protein kinase activity of EIF2AK3/PERK. May play an important role in CKII- and p60c-src-induced signal transduction cascades. May regulate the EFNA5-EPHA3 signaling pathway which modulates cell reorganization and cell-cell repulsion. May also regulate the hepatocyte growth factor receptor signaling pathway through dephosphorylation of MET.
- Gene Name:
- PTPN1
- Uniprot ID:
- P18031
- Molecular Weight:
- 49966.44 Da
References
- Ahn JH, Cho SY, Ha JD, Chu SY, Jung SH, Jung YS, Baek JY, Choi IK, Shin EY, Kang SK, Kim SS, Cheon HG, Yang SD, Choi JK: Synthesis and PTP1B inhibition of 1,2-naphthoquinone derivatives as potent anti-diabetic agents. Bioorg Med Chem Lett. 2002 Aug 5;12(15):1941-6. [12113814 ]
- General Function:
- Serine hydrolase activity
- Specific Function:
- Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
- Gene Name:
- ACHE
- Uniprot ID:
- P22303
- Molecular Weight:
- 67795.525 Da
References
- Hyatt JL, Wadkins RM, Tsurkan L, Hicks LD, Hatfield MJ, Edwards CC, Ross CR 2nd, Cantalupo SA, Crundwell G, Danks MK, Guy RK, Potter PM: Planarity and constraint of the carbonyl groups in 1,2-diones are determinants for selective inhibition of human carboxylesterase 1. J Med Chem. 2007 Nov 15;50(23):5727-34. Epub 2007 Oct 17. [17941623 ]
- General Function:
- Transcriptional activator activity, rna polymerase ii transcription factor binding
- Specific Function:
- Phosphorylation-dependent transcription factor that stimulates transcription upon binding to the DNA cAMP response element (CRE), a sequence present in many viral and cellular promoters. Transcription activation is enhanced by the TORC coactivators which act independently of Ser-133 phosphorylation. Involved in different cellular processes including the synchronization of circadian rhythmicity and the differentiation of adipose cells.
- Gene Name:
- CREB1
- Uniprot ID:
- P16220
- Molecular Weight:
- 36687.86 Da
References
- Endo A, Sumi D, Iwamoto N, Kumagai Y: Inhibition of DNA binding activity of cAMP response element-binding protein by 1,2-naphthoquinone through chemical modification of Cys-286. Chem Biol Interact. 2011 Jul 15;192(3):272-7. doi: 10.1016/j.cbi.2011.04.003. Epub 2011 Apr 20. [21530497 ]
- General Function:
- Peptidyl-cysteine s-nitrosylase activity
- Specific Function:
- Has both glyceraldehyde-3-phosphate dehydrogenase and nitrosylase activities, thereby playing a role in glycolysis and nuclear functions, respectively. Participates in nuclear events including transcription, RNA transport, DNA replication and apoptosis. Nuclear functions are probably due to the nitrosylase activity that mediates cysteine S-nitrosylation of nuclear target proteins such as SIRT1, HDAC2 and PRKDC. Modulates the organization and assembly of the cytoskeleton. Facilitates the CHP1-dependent microtubule and membrane associations through its ability to stimulate the binding of CHP1 to microtubules (By similarity). Glyceraldehyde-3-phosphate dehydrogenase is a key enzyme in glycolysis that catalyzes the first step of the pathway by converting D-glyceraldehyde 3-phosphate (G3P) into 3-phospho-D-glyceroyl phosphate. Component of the GAIT (gamma interferon-activated inhibitor of translation) complex which mediates interferon-gamma-induced transcript-selective translation inhibition in inflammation processes. Upon interferon-gamma treatment assembles into the GAIT complex which binds to stem loop-containing GAIT elements in the 3'-UTR of diverse inflammatory mRNAs (such as ceruplasmin) and suppresses their translation.
- Gene Name:
- GAPDH
- Uniprot ID:
- P04406
- Molecular Weight:
- 36053.0 Da
References
- Miura T, Kakehashi H, Shinkai Y, Egara Y, Hirose R, Cho AK, Kumagai Y: GSH-mediated S-transarylation of a quinone glyceraldehyde-3-phosphate dehydrogenase conjugate. Chem Res Toxicol. 2011 Nov 21;24(11):1836-44. doi: 10.1021/tx200025y. Epub 2011 Sep 1. [21827172 ]
- General Function:
- Triglyceride lipase activity
- Specific Function:
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
- Gene Name:
- CES1
- Uniprot ID:
- P23141
- Molecular Weight:
- 62520.62 Da
References
- Hyatt JL, Wadkins RM, Tsurkan L, Hicks LD, Hatfield MJ, Edwards CC, Ross CR 2nd, Cantalupo SA, Crundwell G, Danks MK, Guy RK, Potter PM: Planarity and constraint of the carbonyl groups in 1,2-diones are determinants for selective inhibition of human carboxylesterase 1. J Med Chem. 2007 Nov 15;50(23):5727-34. Epub 2007 Oct 17. [17941623 ]